Company · CIK 0001267395 · SIC 6331 — Fire, Marine & Casualty Insurance · NYSE

ASPEN INSURANCE HOLDINGS LTD · AHL-PD

Insider activity reported against this company. All insider holders · On EDGAR ↗

Period1M 3M 6M 1Y 2Y All datashares as filed — not split-adjusted

Open-market buys & salesbuys $0 · 0sales $6.3M · 11net −$6.3M

Reported at this company — common stock

Trade	Reported (ET)	Insider	Shares	Avg price	Total	Owned after	Δ stake	Flags
Feb 8, 2016 AForm 4 →	Feb 10, 7:22 am EST	Karl MayrDirector	2,556	—	—	2,556	—	plan?
Feb 8, 2016 AForm 4 →	Feb 10, 7:19 am EST	Glyn JonesDirector	10,952	—	—	128,695	—	plan?
Feb 8, 2016 AForm 4 →	Feb 10, 7:16 am EST	Gordon IrelandDirector	2,190	—	—	10,507	—	plan?
Feb 8, 2016 AForm 4 →	Feb 10, 7:14 am EST	Heidi HutterDirector	2,190	—	—	49,451	—	plan?
Feb 8, 2016 AForm 4 →	Feb 10, 7:11 am EST	Gary R. GreggDirector	2,190	—	—	15,080	—	plan?
Feb 8, 2016 AForm 4 →	Feb 10, 7:08 am EST	John Paul CavooresDirector	2,190	—	—	23,557	—	plan?
Feb 8, 2016 AForm 4 →	Feb 10, 7:01 am EST	Richard J S BucknallDirector	2,190	—	—	33,050	—	plan?
Feb 8, 2016 AForm 4 →	Feb 10, 6:57 am EST	Albert BeerDirector	2,190	—	—	17,392	—	plan?
Feb 8, 2016 AForm 4 →	Feb 10, 6:52 am EST	Liaquat AhamedDirector	2,190	—	—	26,897	—	plan?
Nov 19, 2015 SForm 4 →	Nov 20, 7:31 am EST	Christopher O'KaneCEO, Director	63,500	$50.17	$3,185,916	250,199	−20.2%	plan?
Nov 19, 2015 MForm 4 →	Nov 20, 7:31 am EST	Christopher O'KaneCEO, Director	87,719	$23.65	$2,074,554	313,699	—	plan?
Aug 26, 2015 AForm 4 →	Aug 27, 10:03 am EDT	Heidi HutterDirector	2,000	$21.96	$43,920	47,261	—	plan?
Jun 11, 2015 SForm 4 →	Jun 12, 9:44 am EDT	Karen Ann GreenCEO AIUK Ltd AMAL Ltd	7,500	$47.50	$356,250	23,953	−23.8%	plan?
Apr 28, 2015 SForm 4 →	Apr 29, 9:07 am EDT	Brian BoornazianChairman Aspen Re	751	$47.48	$35,657	10,503	−6.67%	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 11:32 am EDT	Ann HaughCOO & CUO Aspen Insurance	1,891	$47.77	$28,901	681	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 11:29 am EDT	Kate VacherDirector of Underwriting	1,891	$47.77	$28,901	17,979	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 11:28 am EDT	Richard Matthew ThorntonGroup Chief Risk Officer	1,576	$47.77	$24,076	568	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 11:26 am EDT	Villers RupertChairman Aspen Insurance	4,412	$47.77	$67,403	72,999	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 11:21 am EDT	Scott KirkGroup CFO	1,103	$47.77	$16,863	5,251	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 11:17 am EDT	Michael CainCEO, ABL & Group GC	2,008	$47.77	$24,219	25,527	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 11:14 am EDT	Lisa Ms. GibbardHead of IT & Shared Services	1,103	$47.77	$16,863	4,919	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 11:09 am EDT	Christopher O'KaneCEO, Director	12,604	$47.77	$192,513	225,980	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 11:04 am EDT	Stephen PostlewhiteCEO Aspen Re	2,364	$47.77	$36,114	16,432	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 10:59 am EDT	Karen Ann GreenCEO AIUK Ltd AMAL Ltd	1,891	$47.77	$28,901	31,453	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 10:57 am EDT	Mario VitaleCEO Aspen Insurance	6,642	$47.77	$112,498	28,834	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 10:55 am EDT	Emil IssaviPresident, Aspen Re	2,701	$47.77	$41,990	22,459	—	plan?
Apr 25, 2015 AFForm 4 →	Apr 28, 10:49 am EDT	Brian BoornazianChairman Aspen Re	4,461	$47.77	$69,744	11,254	—	plan?
Feb 25, 2015 FForm 4 →	Feb 26, 6:26 am EST	Brian BoornazianChairman Aspen Re	3,874	$45.81	$177,480	9,483	—	plan?
Feb 25, 2015 SForm 4 →	Feb 26, 6:26 am EST	Brian BoornazianChairman Aspen Re	7,021	$45.80	$321,547	13,357	−34.5%	plan?
Feb 23, 2015 AFForm 4 →	Feb 25, 12:16 pm EST	Brian BoornazianChairman Aspen Re	38,225	$46.04	$467,561	20,378	—	plan?
Feb 23, 2015 AFForm 4 →	Feb 25, 11:16 am EST	Stephen PostlewhiteCEO Aspen Re	20,862	$46.09	$314,628	15,580	—	plan?
Feb 23, 2015 AFForm 4 →	Feb 25, 11:12 am EST	Emil IssaviPresident, Aspen Re	18,914	$46.08	$224,819	21,516	—	plan?
Feb 23, 2015 AFForm 4 →	Feb 25, 11:00 am EST	Karen Ann GreenCEO AIUK Ltd AMAL Ltd	17,387	$46.10	$262,234	30,772	—	plan?
Feb 23, 2015 AFForm 4 →	Feb 25, 10:53 am EST	Mario VitaleCEO Aspen Insurance	40,047	$46.04	$551,376	26,902	—	plan?
Feb 23, 2015 AFForm 4 →	Feb 25, 10:50 am EST	Christopher O'KaneCEO, Director	69,525	$46.04	$1,047,055	221,436	—	plan?
Feb 23, 2015 AFForm 4 →	Feb 25, 10:48 am EST	Kate VacherDirector of Underwriting	16,690	$46.11	$251,739	17,298	—	plan?
Feb 23, 2015 AFForm 4 →	Feb 25, 10:42 am EST	Michael CainCEO, ABL & Group GC	20,862	$46.09	$314,622	24,533	—	plan?
Feb 23, 2015 AFForm 4 →	Feb 25, 10:39 am EST	Villers RupertChairman Aspen Insurance	41,719	$46.06	$628,730	71,409	—	plan?
Feb 12, 2015 SForm 4 →	Feb 13, 2:02 pm EST	Brian BoornazianChairman Aspen Re	1,920	$46.54	$89,350	2,463	−43.8%	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 2:02 pm EST	Brian BoornazianChairman Aspen Re	5,518	$46.07	$101,718	3,530	—	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 1:56 pm EST	Villers RupertChairman Aspen Insurance	4,866	$45.65	$71,031	56,988	—	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 1:53 pm EST	Lisa Ms. GibbardHead of IT & Shared Services	834	$45.65	$12,189	4,522	—	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 1:49 pm EST	Scott KirkGroup CFO	938	$45.65	$13,695	4,854	—	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 1:43 pm EST	Michael CainCEO, ABL & Group GC	2,433	$45.65	$35,516	17,325	—	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 1:39 pm EST	Christopher O'KaneCEO, Director	9,907	$45.65	$144,619	196,735	—	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 1:33 pm EST	Karen Ann GreenCEO AIUK Ltd AMAL Ltd	2,085	$45.65	$30,449	24,763	—	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 1:30 pm EST	Emil IssaviPresident, Aspen Re	2,200	$45.65	$24,879	12,360	—	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 1:25 pm EST	Stephen PostlewhiteCEO Aspen Re	2,607	$45.65	$38,072	8,372	—	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 1:20 pm EST	Mario VitaleCEO Aspen Insurance	4,645	$45.65	$60,943	10,809	—	plan?
Feb 11, 2015 AFForm 4 →	Feb 13, 1:18 pm EST	Kate VacherDirector of Underwriting	2,085	$45.65	$30,449	11,528	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:45 am EST	Glyn JonesDirector	12,154	—	—	117,743	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:44 am EST	Gordon IrelandDirector	2,762	—	—	8,317	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:41 am EST	Heidi HutterDirector	2,762	—	—	45,261	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:40 am EST	Liaquat AhamedDirector	2,762	—	—	24,707	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:34 am EST	Gary R. GreggDirector	2,762	—	—	12,890	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:33 am EST	Richard J S BucknallDirector	2,762	—	—	30,860	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:29 am EST	Albert BeerDirector	2,762	—	—	15,202	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:27 am EST	Bret D PearlmanDirector	2,762	—	—	6,929	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:16 am EST	Ronald R PressmanDirector	2,762	—	—	12,601	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:11 am EST	John Paul CavooresDirector	2,762	—	—	21,367	—	plan?
Feb 9, 2015 AForm 4 →	Feb 11, 10:10 am EST	Peter O'FlinnDirector	2,762	—	—	21,947	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:45 am EST	Stephen PostlewhiteCEO Aspen Re	3,123	$45.10	$45,055	7,433	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:42 am EST	Villers RupertChairman Aspen Insurance	6,247	$45.10	$90,110	53,236	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:33 am EST	Michael CainCEO, ABL & Group GC	3,123	$45.10	$45,055	15,449	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:30 am EST	Scott KirkGroup CFO	1,041	$45.10	$15,018	4,183	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:27 am EST	Christopher O'KaneCEO, Director	10,411	$45.10	$150,138	193,164	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:24 am EST	Karen Ann GreenCEO AIUK Ltd AMAL Ltd	2,602	$45.10	$37,523	24,012	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:21 am EST	Kate VacherDirector of Underwriting	2,499	$45.10	$36,035	10,777	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:19 am EST	Mario VitaleCEO Aspen Insurance	6,008	$45.10	$79,331	8,834	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:17 am EST	Brian BoornazianChairman Aspen Re	5,761	$45.10	$68,191	3,281	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:14 am EST	Emil IssaviPresident, Aspen Re	2,919	$45.10	$35,855	11,250	—	plan?
Feb 8, 2015 AFForm 4 →	Feb 10, 7:08 am EST	Lisa Ms. GibbardHead of IT & Shared Services	833	$45.10	$12,042	3,955	—	plan?
Feb 3, 2015 SForm 4 →	Feb 5, 4:17 pm EST	Christopher O'KaneCEO, Director	28,669	$45.00	$1,290,105	189,411	−13.1%	plan?
Feb 3, 2015 MForm 4 →	Feb 5, 4:17 pm EST	Christopher O'KaneCEO, Director	28,669	$27.28	$782,090	200,230	—	plan?

Reported at this company — derivatives (options, RSUs, warrants)

Trade	Reported (ET)	Insider	Shares	Avg price	Total	Owned after	Δ stake
Apr 25, 2015 MForm 4 →	Apr 28, 11:26 am EDT	Villers RupertChairman Aspen Insurance	3,001	—	—	6,001	—
Apr 25, 2015 MForm 4 →	Apr 28, 11:21 am EDT	Scott KirkGroup CFO	750	—	—	1,500	—
Apr 25, 2015 MForm 4 →	Apr 28, 11:17 am EDT	Michael CainCEO, ABL & Group GC	1,501	—	—	3,000	—
Apr 25, 2015 MForm 4 →	Apr 28, 11:14 am EDT	Lisa Ms. GibbardHead of IT & Shared Services	750	—	—	1,500	—
Apr 25, 2015 MForm 4 →	Apr 28, 11:09 am EDT	Christopher O'KaneCEO, Director	8,574	—	—	17,146	—
Apr 25, 2015 MForm 4 →	Apr 28, 11:04 am EDT	Stephen PostlewhiteCEO Aspen Re	1,608	—	—	3,214	—
Apr 25, 2015 MForm 4 →	Apr 28, 10:59 am EDT	Karen Ann GreenCEO AIUK Ltd AMAL Ltd	1,286	—	—	2,572	—
Apr 25, 2015 MForm 4 →	Apr 28, 10:57 am EDT	Mario VitaleCEO Aspen Insurance	4,287	—	—	8,573	—
Apr 25, 2015 MForm 4 →	Apr 28, 10:55 am EDT	Emil IssaviPresident, Aspen Re	1,822	—	—	3,643	—
Apr 25, 2015 MForm 4 →	Apr 28, 10:49 am EDT	Brian BoornazianChairman Aspen Re	3,001	—	—	6,001	—
Mar 5, 2015 AForm 4 →	Mar 9, 12:11 pm EDT	Michael CainCEO, ABL & Group GC	3,925	—	—	3,925	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:50 am EDT	Christopher O'KaneCEO, Director	22,431	—	—	22,431	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:49 am EDT	Brian BoornazianChairman Aspen Re	8,411	—	—	8,411	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:46 am EDT	Lisa Ms. GibbardHead of IT & Shared Services	1,962	—	—	1,962	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:44 am EDT	Karen Ann GreenCEO AIUK Ltd AMAL Ltd	3,364	—	—	3,364	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:41 am EDT	Ann HaughCOO & CUO Aspen Insurance	4,205	—	—	4,205	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:40 am EDT	Emil IssaviPresident, Aspen Re	8,411	—	—	8,411	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:38 am EDT	Scott KirkGroup CFO	5,607	—	—	5,607	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:37 am EDT	Stephen PostlewhiteCEO Aspen Re	9,813	—	—	9,813	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:35 am EDT	Richard Matthew ThorntonGroup Chief Risk Officer	3,364	—	—	3,364	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:33 am EDT	Kate VacherDirector of Underwriting	3,364	—	—	3,364	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:31 am EDT	Villers RupertChairman Aspen Insurance	7,851	—	—	7,851	—
Mar 5, 2015 AForm 4 →	Mar 9, 11:29 am EDT	Mario VitaleCEO Aspen Insurance	9,813	—	—	9,813	—
Feb 23, 2015 AMForm 4 →	Feb 25, 12:16 pm EST	Brian BoornazianChairman Aspen Re	68,435	—	—	11,613	—
Feb 23, 2015 AMForm 4 →	Feb 25, 11:16 am EST	Stephen PostlewhiteCEO Aspen Re	35,090	—	—	6,222	—
Feb 23, 2015 AMForm 4 →	Feb 25, 11:12 am EST	Emil IssaviPresident, Aspen Re	35,463	—	—	7,052	—
Feb 23, 2015 AMForm 4 →	Feb 25, 11:12 am EST	Lisa Ms. GibbardHead of IT & Shared Services	6,152	—	—	2,904	—
Feb 23, 2015 AForm 4 →	Feb 25, 11:06 am EST	Ann HaughCOO & CUO Aspen Insurance	4,977	—	—	4,977	—
Feb 23, 2015 AMForm 4 →	Feb 25, 11:05 am EST	Scott KirkGroup CFO	6,871	—	—	1,021	—
Feb 23, 2015 AForm 4 →	Feb 25, 11:01 am EST	Richard Matthew ThorntonGroup Chief Risk Officer	1,383	—	—	1,383	—
Feb 23, 2015 AMForm 4 →	Feb 25, 11:00 am EST	Karen Ann GreenCEO AIUK Ltd AMAL Ltd	28,809	—	—	4,977	—
Feb 23, 2015 AMForm 4 →	Feb 25, 10:53 am EST	Mario VitaleCEO Aspen Insurance	73,412	—	—	16,590	—
Feb 23, 2015 AMForm 4 →	Feb 25, 10:50 am EST	Christopher O'KaneCEO, Director	132,590	—	—	33,179	—
Feb 23, 2015 AMForm 4 →	Feb 25, 10:48 am EST	Kate VacherDirector of Underwriting	28,074	—	—	4,977	—
Feb 23, 2015 AMForm 4 →	Feb 25, 10:42 am EST	Michael CainCEO, ABL & Group GC	34,218	—	—	5,807	—
Feb 23, 2015 AMForm 4 →	Feb 25, 10:39 am EST	Villers RupertChairman Aspen Insurance	68,435	—	—	11,613	—
Feb 11, 2015 MForm 4 →	Feb 13, 2:02 pm EST	Brian BoornazianChairman Aspen Re	3,310	—	—	3,310	—
Feb 11, 2015 MForm 4 →	Feb 13, 1:56 pm EST	Villers RupertChairman Aspen Insurance	3,310	—	—	3,310	—
Feb 11, 2015 MForm 4 →	Feb 13, 1:53 pm EST	Lisa Ms. GibbardHead of IT & Shared Services	567	—	—	567	—
Feb 11, 2015 MForm 4 →	Feb 13, 1:49 pm EST	Scott KirkGroup CFO	638	—	—	638	—
Feb 11, 2015 MForm 4 →	Feb 13, 1:43 pm EST	Michael CainCEO, ABL & Group GC	1,655	—	—	1,655	—
Feb 11, 2015 MForm 4 →	Feb 13, 1:39 pm EST	Christopher O'KaneCEO, Director	6,739	—	—	6,739	—
Feb 11, 2015 MForm 4 →	Feb 13, 1:33 pm EST	Karen Ann GreenCEO AIUK Ltd AMAL Ltd	1,418	—	—	1,419	—
Feb 11, 2015 MForm 4 →	Feb 13, 1:30 pm EST	Emil IssaviPresident, Aspen Re	1,655	—	—	1,655	—
Feb 11, 2015 MForm 4 →	Feb 13, 1:25 pm EST	Stephen PostlewhiteCEO Aspen Re	1,773	—	—	1,773	—
Feb 11, 2015 MForm 4 →	Feb 13, 1:20 pm EST	Mario VitaleCEO Aspen Insurance	3,310	—	—	3,310	—
Feb 11, 2015 MForm 4 →	Feb 13, 1:18 pm EST	Kate VacherDirector of Underwriting	1,418	—	—	1,419	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:45 am EST	Stephen PostlewhiteCEO Aspen Re	2,124	—	—	0	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:42 am EST	Villers RupertChairman Aspen Insurance	4,249	—	—	0	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:33 am EST	Michael CainCEO, ABL & Group GC	2,124	—	—	0	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:30 am EST	Scott KirkGroup CFO	708	—	—	0	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:27 am EST	Christopher O'KaneCEO, Director	7,082	—	—	0	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:24 am EST	Karen Ann GreenCEO AIUK Ltd AMAL Ltd	1,770	—	—	0	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:21 am EST	Kate VacherDirector of Underwriting	1,700	—	—	0	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:19 am EST	Mario VitaleCEO Aspen Insurance	4,249	—	—	0	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:17 am EST	Brian BoornazianChairman Aspen Re	4,249	—	—	0	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:14 am EST	Emil IssaviPresident, Aspen Re	2,124	—	—	0	—
Feb 8, 2015 MForm 4 →	Feb 10, 7:08 am EST	Lisa Ms. GibbardHead of IT & Shared Services	566	—	—	0	—
Feb 3, 2015 MForm 4 →	Feb 5, 4:17 pm EST	Christopher O'KaneCEO, Director	28,669	—	—	0	—
Jan 14, 2015 JForm 4 →	Jan 16, 4:00 pm EST	John A WorthOther	4,822	—	—	0	—