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O Kane Christopher

Disclosed activity across 1 company

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160050
SEC CIK
0001561313

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Latest disclosed role at each company.

No relationships currently tracked through insider filings.

Disclosed balances

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Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

No balances currently tracked through insider filings.

Past disclosures · reporting ended (1)

No longer tracked through insider filings. These historical balances do not imply present ownership or a zero position.

ASPEN INSURANCE HOLDINGS LTD

Report date February 15, 2019 · Filed February 20, 2019

Section 16 reporting ended · disclosed 2019-02-20. Current position is not established by this disclosure.

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
2017 Performance SharesSEC Table II · derivative / convertible securityDirect17,784 Reported balance After 2019-02-15 transaction · row 1 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 1 · 2019-02-15 · Grant · Acquired 17,784 · Balance 17,784

F1: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3: At the effective time of the Merger, each 2017 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Performance Share.

F2: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

2017 Performance SharesSEC Table II · derivative / convertible securityDirect0 Reported balance After 2019-02-15 transaction · row 2 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 2 · 2019-02-15 · Disposition to issuer · Disposed 17,784 · Balance 0

F1: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F4: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F3: At the effective time of the Merger, each 2017 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Performance Share.

F2: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

Performance Shares (2018 Grant)SEC Table II · derivative / convertible securityDirect41,484 Reported balance After 2019-02-15 transaction · row 3 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 3 · 2019-02-15 · Grant · Acquired 41,484 · Balance 41,484

F1: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

F5: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

Performance Shares (2018 Grant)SEC Table II · derivative / convertible securityDirect0 Reported balance After 2019-02-15 transaction · row 4 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 4 · 2019-02-15 · Disposition to issuer · Disposed 41,484 · Balance 0

F1: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

F5: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

Filing footnotes · ownership attribution and instrument terms

F1: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F2: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

F3: At the effective time of the Merger, each 2017 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Performance Share.

F4: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F5: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

F6: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
February 15, 2019 Filed Feb 15, 2019 22:27 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Disposition to issuerRestricted Share Units (2018 Grant) · Derivative 13,828 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · derivative · entry 6

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 13,828 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F11 · price: At the effective time of the Merger, each 2018 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2018 Restricted Share Unit award, which had not previously been settled.

F10 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason.

F10 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Restricted Share Units were scheduled to vest annually in increments of one third on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason.

Read SEC document
February 15, 2019 Filed Feb 15, 2019 22:27 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Disposition to issuerRestricted Share Units (2017 Grant) · Derivative 5,928 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · derivative · entry 5

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 5,928 shares

Expires not disclosed

F7 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F9 · price: At the effective time of the Merger, each 2017 Restricted Share Unit that was outstanding immediately prior to the effective time of the Merger was cancelled and converted into the right to receive a lump-sum amount in cash, without interest, equal to the product of (x) the sum of (1) $42.75 and (2) any per share accrued dividend equivalents times (y) the number of ordinary shares subject to such 2017 Restricted Share Unit award, which had not previously been settled.

F8 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason.

F8 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Restricted Share Units were scheduled to vest annually in increments of one third on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason.

Read SEC document
February 15, 2019 Filed Feb 15, 2019 22:27 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Disposition to issuerOrdinary Shares 238,494 $42.75 $10,195,618.50
Disclosure

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · nonDerivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F3 · kind: This Form 4 is being filed, in part, as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F4 · shares: At the effective time of the Merger, each outstanding ordinary share of the Issuer was converted into a right to receive a cash payment of $42.75 without any interest and less any applicable withholding tax.

Read SEC document
February 15, 2019 Filed Feb 20, 2019 17:55 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Disposition to issuerPerformance Shares (2018 Grant) · Derivative 41,484 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000006 · wf-form4_155068530580321.xml · derivative · entry 4

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 41,484 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

F5 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

F5 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

Read SEC document
February 15, 2019 Filed Feb 20, 2019 17:55 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantPerformance Shares (2018 Grant) · Derivative 41,484 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000006 · wf-form4_155068530580321.xml · derivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 41,484

Underlying: Ordinary Shares · 41,484 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: At the effective time of the Merger, each 2018 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2018 Performance Share.

F5 · derivative.exercise_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

F5 · derivative.expiration_date: At the time of grant on February 9, 2018, the 2018 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2018 Performance Share award was tested annually over a three-year period. All vested 2018 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2020. One third of the 2018 Performance Shares were forfeited based on the Issuer's 2018 adjusted annual growth in diluted book value per ordinary share test and two thirds of the 2018 Performance Shares vested at target payout levels in connection with the Merger.

Read SEC document
February 15, 2019 Filed Feb 20, 2019 17:55 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Disposition to issuer2017 Performance Shares · Derivative 17,784 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000006 · wf-form4_155068530580321.xml · derivative · entry 2

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 17,784 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F4 · kind: This Form 4 is being filed as a result of the closing on February 15, 2019 of the merger (the "Merger") as described in the Agreement and Plan of Merger, dated as of August 27, 2018 (the "Merger Agreement") among Aspen Insurance Holdings Limited (the "Issuer"), Highlands Holdings, Ltd., and Highlands Merger Sub, Ltd.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: At the effective time of the Merger, each 2017 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Performance Share.

F2 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

F2 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

Read SEC document
February 15, 2019 Filed Feb 20, 2019 17:55 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Grant2017 Performance Shares · Derivative 17,784 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000006 · wf-form4_155068530580321.xml · derivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,784

Underlying: Ordinary Shares · 17,784 shares

Expires not disclosed

F1 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F1 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: At the effective time of the Merger, each 2017 Performance Share outstanding immediately prior to the Merger was, to the extent not vested, fully vested, and was canceled and converted into the right to receive a lump-sum amount in cash, equal to $42.75, without interest and less any applicable tax withholding, per 2017 Performance Share.

F2 · derivative.exercise_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

F2 · derivative.expiration_date: At the time of grant on February 10, 2017, the 2017 Performance Shares were eligible for vesting following the achievement of certain financial targets by the Issuer. Prior to the Merger, one third of the 2017 Performance Share award was tested annually over a three-year period. All vested 2017 Performance Shares would have been issued following the filing of the annual report on Form 10-K for the year ended December 31, 2019. Two thirds of the 2017 Performance Shares were forfeited based on the Issuer's 2017 and 2018 adjusted annual growth in diluted book value per ordinary share test and one third of the 2017 Performance Shares vested at target payout levels in connection with the Merger.

Read SEC document
February 13, 2019 Filed Feb 15, 2019 22:27 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversion2016 Performance Shares · Derivative 7,909 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · derivative · entry 4

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 7,909 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · derivative.exercise_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

F6 · derivative.expiration_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award was tested annually over a three-year period. All vested 2016 Performance Shares were issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

Read SEC document
February 13, 2019 Filed Feb 15, 2019 22:27 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 2,662 $42.51 $113,161.62
Disclosure

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · nonDerivative · entry 2

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 238,494

F2 · kind: Ordinary shares sold in order to satisfy tax liability upon vesting of previously granted Performance Shares.

Read SEC document
February 13, 2019 Filed Feb 15, 2019 22:27 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 7,909 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000004 · wf-form4_155026961903788.xml · nonDerivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 241,156

F1 · price: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met.

Read SEC document
February 10, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversionRestricted Share Units (2017 Grant) · Derivative 5,928 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · derivative · entry 12

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 5,928

Underlying: Ordinary Shares · 5,928 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F6 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F10 · derivative.exercise_date: Represents 2017 Restricted Share Units granted on February 10, 2017 under our 2013 Share Incentive Plan. One-third of the 2017 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2017 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F10 · derivative.expiration_date: Represents 2017 Restricted Share Units granted on February 10, 2017 under our 2013 Share Incentive Plan. One-third of the 2017 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2017 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
February 10, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 1,530 $42.56 $65,116.80
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · nonDerivative · entry 8

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 233,247

F5 · kind: Ordinary shares withheld in order to satisfy tax liability in connection with previously granted 2017 Restricted Share Units.

Read SEC document
February 10, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 5,928 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · nonDerivative · entry 7

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 234,777

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

Read SEC document
February 09, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversionRestricted Share Units (2018 Grant) · Derivative 6,915 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · derivative · entry 11

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,828

Underlying: Ordinary Shares · 6,915 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F6 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F9 · derivative.exercise_date: Represents 2018 Restricted Share Units granted on February 9, 2018 under our 2013 Share Incentive Plan, as amended. One-third of the 2018 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2018 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F9 · derivative.expiration_date: Represents 2018 Restricted Share Units granted on February 9, 2018 under our 2013 Share Incentive Plan, as amended. One-third of the 2018 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2018 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
February 09, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 1,785 $42.56 $75,969.60
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · nonDerivative · entry 6

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 228,849

F4 · kind: Ordinary shares withheld in order to satisfy tax liability in connection with previously granted 2018 Restricted Share Units.

Read SEC document
February 09, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 6,915 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · nonDerivative · entry 5

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 230,634

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversionRestricted Share Units (2016 Grant) · Derivative 7,302 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · derivative · entry 10

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 7,302 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F6 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F8 · derivative.exercise_date: Represents 2016 Restricted Share Units granted on February 8, 2016 under our 2013 Share Incentive Plan, as amended. One-third of the 2016 Restricted Share Units vested annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2016 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F8 · derivative.expiration_date: Represents 2016 Restricted Share Units granted on February 8, 2016 under our 2013 Share Incentive Plan, as amended. One-third of the 2016 Restricted Share Units vested annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2016 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversionRestricted Share Units (2015 Part Bonus) · Derivative 2,439 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · derivative · entry 9

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 2,439 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F6 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · derivative.exercise_date: Represents a portion of the Reporting Person's annual bonus for 2015 paid in Restricted Share Units. The Restricted Share Units were granted on February 8, 2016. One-third of the Restricted Share Units vested annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason. Upon vesting of the Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F7 · derivative.expiration_date: Represents a portion of the Reporting Person's annual bonus for 2015 paid in Restricted Share Units. The Restricted Share Units were granted on February 8, 2016. One-third of the Restricted Share Units vested annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason. Upon vesting of the Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 1,884 $42.56 $80,183.04
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · nonDerivative · entry 4

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 223,719

F3 · kind: Ordinary shares withheld in order to satisfy tax liability in connection with previously granted 2016 Restricted Share Units.

Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 7,302 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · nonDerivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 225,603

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 630 $42.56 $26,812.80
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · nonDerivative · entry 2

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 218,301

F2 · kind: Ordinary shares withheld in order to satisfy tax liability in connection with previously granted 2015 Part Bonus Restricted Share Units.

Read SEC document
February 08, 2019 Filed Feb 12, 2019 20:42 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 2,439 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-19-000002 · wf-form4_155000412473504.xml · nonDerivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 218,931

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

Read SEC document
May 10, 2018 Filed May 11, 2018 14:30 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 354 $39.05 $13,823.70
Disclosure

SEC source: 0001561313-18-000009 · wf-form4_152604898434226.xml · nonDerivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 216,492

F1 · price: The Reporting Person is voluntarily reporting the acquisition of ordinary shares from the Issuer's Share Purchase Plan which is otherwise exempt from Form 4 reporting under Rule 16a-3(f) of the SecuritiesExchange Act of 1934, as amended.

Read SEC document
March 05, 2018 Filed Mar 7, 2018 20:36 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversion2015 Performance Shares · Derivative 29,072 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000007 · wf-form4_152045493774488.xml · derivative · entry 6

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 29,072 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F7 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F8 · derivative.exercise_date: Represents 2015 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2015 Performance Share award is tested annually over a three-year period.

F8 · derivative.expiration_date: Represents 2015 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2015 Performance Share award is tested annually over a three-year period.

Read SEC document
March 05, 2018 Filed Mar 7, 2018 20:36 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversionRestricted Share Units (2015 Grant) · Derivative 7,477 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000007 · wf-form4_152045493774488.xml · derivative · entry 5

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 7,477 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · derivative.exercise_date: Represents 2015 Restricted Share Units granted on March 5, 2015 under our 2013 Share Incentive Plan, as amended. One-third of the 2015 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2015 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F6 · derivative.expiration_date: Represents 2015 Restricted Share Units granted on March 5, 2015 under our 2013 Share Incentive Plan, as amended. One-third of the 2015 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2015 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
March 05, 2018 Filed Mar 7, 2018 20:36 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 13,665 $37.95 $518,586.75
Disclosure

SEC source: 0001561313-18-000007 · wf-form4_152045493774488.xml · nonDerivative · entry 4

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 216,138

F4 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Performance Shares.

Read SEC document
March 05, 2018 Filed Mar 7, 2018 20:36 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 29,072 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000007 · wf-form4_152045493774488.xml · nonDerivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 229,803

F3 · price: Ordinary shares acquired upon mandatory conversion of Performance Shares in accordance with the performance conditions having been met.

Read SEC document
March 05, 2018 Filed Mar 7, 2018 20:36 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 3,515 $37.95 $133,394.25
Disclosure

SEC source: 0001561313-18-000007 · wf-form4_152045493774488.xml · nonDerivative · entry 2

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 200,731

F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units.

Read SEC document
March 05, 2018 Filed Mar 7, 2018 20:36 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 7,477 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000007 · wf-form4_152045493774488.xml · nonDerivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 204,246

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

Read SEC document
February 10, 2018 Filed Feb 13, 2018 23:48 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversionRestricted Share Units (2017 Grant) · Derivative 5,928 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000004 · wf-form4_151856566855485.xml · derivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,856

Underlying: Ordinary Shares · 5,928 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F4 · derivative.exercise_date: Represents 2017 Restricted Share Units granted on February 10, 2017 under our 2013 Share Incentive Plan, as amended. One-third of the 2017 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2017 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F4 · derivative.expiration_date: Represents 2017 Restricted Share Units granted on February 10, 2017 under our 2013 Share Incentive Plan, as amended. One-third of the 2017 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2017 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
February 10, 2018 Filed Feb 13, 2018 23:48 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 2,787 $36.75 $102,422.25
Disclosure

SEC source: 0001561313-18-000004 · wf-form4_151856566855485.xml · nonDerivative · entry 2

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 196,769

F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units.

Read SEC document
February 10, 2018 Filed Feb 13, 2018 23:48 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 5,928 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000004 · wf-form4_151856566855485.xml · nonDerivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 199,556

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

Read SEC document
February 09, 2018 Filed Feb 13, 2018 23:48 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantRestricted Share Units (2018 Grant) · Derivative 20,743 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000004 · wf-form4_151856566855485.xml · derivative · entry 4

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 20,743

Underlying: Ordinary Shares · 20,743 shares

Expires not disclosed

F3 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · derivative.exercise_date: Represents 2018 Restricted Share Units granted on February 9, 2018 under our 2013 Share Incentive Plan, as amended. One-third of the 2018 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2018 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F5 · derivative.expiration_date: Represents 2018 Restricted Share Units granted on February 9, 2018 under our 2013 Share Incentive Plan, as amended. One-third of the 2018 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2018 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:02 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversionRestricted Share Units (2015 Part Bonus) · Derivative 2,438 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000002 · wf-form4_151845134312762.xml · derivative · entry 6

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,439

Underlying: Ordinary Shares · 2,438 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · derivative.exercise_date: Represents a portion of the Reporting Person's annual bonus for 2015 paid in Restricted Share Units. The Restricted Share Units were granted on February 8, 2016. One-third of the Restricted Share Units vest annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason. Upon vesting of the Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F5 · derivative.expiration_date: Represents a portion of the Reporting Person's annual bonus for 2015 paid in Restricted Share Units. The Restricted Share Units were granted on February 8, 2016. One-third of the Restricted Share Units vest annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service, unless terminated without cause or by the Reporting Person for good reason. Upon vesting of the Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:02 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversionRestricted Share Units (2016 Grant) · Derivative 7,302 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000002 · wf-form4_151845134312762.xml · derivative · entry 5

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 7,302

Underlying: Ordinary Shares · 7,302 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F4 · derivative.exercise_date: Represents 2016 Restricted Share Units granted on February 8, 2016 under our 2013 Share Incentive Plan, as amended. One-third of the 2016 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2016 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F4 · derivative.expiration_date: Represents 2016 Restricted Share Units granted on February 8, 2016 under our 2013 Share Incentive Plan, as amended. One-third of the 2016 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2016 Restricted Share Units, the Reporting Person shall be entitled to receive a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:02 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 1,146 $37.00 $42,402.00
Disclosure

SEC source: 0001561313-18-000002 · wf-form4_151845134312762.xml · nonDerivative · entry 4

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 193,628

F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units.

Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:02 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 2,438 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000002 · wf-form4_151845134312762.xml · nonDerivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 194,774

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:02 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 3,432 $37.00 $126,984.00
Disclosure

SEC source: 0001561313-18-000002 · wf-form4_151845134312762.xml · nonDerivative · entry 2

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 192,336

F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units.

Read SEC document
February 08, 2018 Filed Feb 12, 2018 16:02 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 7,302 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-18-000002 · wf-form4_151845134312762.xml · nonDerivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 195,768

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

Read SEC document
December 13, 2017 Filed Dec 15, 2017 11:15 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 410 $36.27 $14,870.70
Disclosure

SEC source: 0001561313-17-000012 · wf-form4_151333653293587.xml · nonDerivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 188,466

F1 · price: The Reporting Person is voluntarily reporting the acquisition of ordinary shares from the Issuer's Share Purchase Plan which is otherwise exempt from Form 4 reporting under Rule 16a-3(f) of the Securities Exchange Act of 1934, as amended.

F2 · balance_after: The number of ordinary shares outstanding differs from the Reporting Person's previously filed Form 4 due to a transaction that was exempt from reporting on Form 4.

Read SEC document
April 25, 2017 Filed Apr 27, 2017 18:09 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversionRestricted Share Units (2014 Grant) · Derivative 8,573 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-17-000010 · wf-form4_149331655086515.xml · derivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 8,573 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F4 · derivative.exercise_date: Represents 2014 Restricted Share Units granted on April 25, 2014 under our 2013 Share Incentive Plan as amended. One-third of the 2014 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2014 Restricted Share Units, the Reporting Person shall be entitled to received a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F4 · derivative.expiration_date: Represents 2014 Restricted Share Units granted on April 25, 2014 under our 2013 Share Incentive Plan as amended. One-third of the 2014 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2014 Restricted Share Units, the Reporting Person shall be entitled to received a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
April 25, 2017 Filed Apr 27, 2017 18:09 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 4,030 $51.50 $207,545.00
Disclosure

SEC source: 0001561313-17-000010 · wf-form4_149331655086515.xml · nonDerivative · entry 2

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 206,056

F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units.

Read SEC document
April 25, 2017 Filed Apr 27, 2017 18:09 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 8,573 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-17-000010 · wf-form4_149331655086515.xml · nonDerivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 210,086

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

Read SEC document
March 05, 2017 Filed Mar 7, 2017 15:25 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversionRestricted Share Units (2015 Grant) · Derivative 7,477 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-17-000008 · wf-form4_148890030819628.xml · derivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 7,477

Underlying: Ordinary Shares · 7,477 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Restricted Share Unit represents the right to receive one share of the Issuer's Ordinary Shares.

F4 · derivative.exercise_date: Represents 2015 Restricted Share Units granted on March 5, 2015 under our 2013 Share Incentive Plan. One-third of the 2015 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2015 Restricted Share Units, the Reporting Person shall be entitled to received a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

F4 · derivative.expiration_date: Represents 2015 Restricted Share Units granted on March 5, 2015 under our 2013 Share Incentive Plan. One-third of the 2015 Restricted Share Units vests annually on the anniversary of the grant date over a three-year period, in each case subject to the Reporting Person's continued service. Upon vesting of the 2015 Restricted Share Units, the Reporting Person shall be entitled to received a number of Ordinary Shares equal to the number of Restricted Share Units then vesting.

Read SEC document
March 05, 2017 Filed Mar 7, 2017 15:25 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Tax withholdingOrdinary Shares 3,515 $56.35 $198,070.25
Disclosure

SEC source: 0001561313-17-000008 · wf-form4_148890030819628.xml · nonDerivative · entry 2

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 201,513

F2 · kind: Ordinary shares withheld in order to satisfy tax liability upon vesting of previously granted Restricted Share Units.

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March 05, 2017 Filed Mar 7, 2017 15:25 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 GrantOrdinary Shares 7,477 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-17-000008 · wf-form4_148890030819628.xml · nonDerivative · entry 1

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 205,028

F1 · price: Ordinary shares acquired upon mandatory conversion of previously granted Restricted Share Units.

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February 22, 2017 Filed Feb 24, 2017 22:52 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Grant2016 Performance Shares · Derivative 7,908 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-17-000006 · wf-form4_148797673005108.xml · derivative · entry 6

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 7,908

Underlying: Ordinary Shares · 7,908 shares

Expires not disclosed

F3 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F7 · derivative.exercise_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award is tested annually over a three-year period. All vested 2016 Performance Shares will be issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

F7 · derivative.expiration_date: Represents 2016 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2016 Performance Share award is tested annually over a three-year period. All vested 2016 Performance Shares will be issued following the filing of the annual report on Form 10-K for the year ended December 31, 2018.

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February 22, 2017 Filed Feb 24, 2017 22:52 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Grant2015 Performance Shares · Derivative 8,098 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-17-000006 · wf-form4_148797673005108.xml · derivative · entry 5

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 29,072

Underlying: Ordinary Shares · 8,098 shares

Expires not disclosed

F3 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F6 · derivative.exercise_date: Represents 2015 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2015 Performance Share award is tested annually over a three-year period. All vested 2015 Performance Shares will be issued following the filing of the annual report on Form 10-K for the year ended December 31, 2017.

F6 · derivative.expiration_date: Represents 2015 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2015 Performance Share award is tested annually over a three-year period. All vested 2015 Performance Shares will be issued following the filing of the annual report on Form 10-K for the year ended December 31, 2017.

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February 22, 2017 Filed Feb 24, 2017 22:52 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Exercise / conversion2014 Performance Shares · Derivative 66,513 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-17-000006 · wf-form4_148797673005108.xml · derivative · entry 4

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

Underlying: Ordinary Shares · 66,513 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F5 · derivative.exercise_date: Represents mandatory conversion into Issuer's Ordinary Shares of all 2014 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer and filing of the annual report on Form 10-K for the year ended December 31, 2016.

F5 · derivative.expiration_date: Represents mandatory conversion into Issuer's Ordinary Shares of all 2014 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer and filing of the annual report on Form 10-K for the year ended December 31, 2016.

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February 22, 2017 Filed Feb 24, 2017 22:52 UTC ASPEN INSURANCE HOLDINGS LTD AHL · Entity 9774 Grant2014 Performance Shares · Derivative 9,285 Not disclosed Not disclosed
Disclosure

SEC source: 0001561313-17-000006 · wf-form4_148797673005108.xml · derivative · entry 3

O Kane Christopher · CIK 0001561313 · Director · CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 66,513

Underlying: Ordinary Shares · 9,285 shares

Expires not disclosed

F3 · derivative.exercise_price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F3 · price: Each Performance Share represents the right to receive one share of the Issuer's Ordinary Shares.

F4 · derivative.exercise_date: Represents 2014 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2014 Performance Share award is tested annually over a three-year period. All vested 2014 Performance Shares are issued following the filing of the annual report on Form 10-K for the year ended December 31, 2016.

F4 · derivative.expiration_date: Represents 2014 Performance Shares eligible for vesting following the achievement of certain financial targets by the Issuer. One third of the 2014 Performance Share award is tested annually over a three-year period. All vested 2014 Performance Shares are issued following the filing of the annual report on Form 10-K for the year ended December 31, 2016.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.