Hamilton Insurance Group, Ltd. (HG) Insider Trading

Last 12 months

Insiders bought $3k and sold $6.48M on the open market.

None of the selling was scheduled in advance under a 10b5-1 plan. Chief Underwriting Officer Timothy James Duffin sold $1.97M on Sep 11, 23% of their stake, outside a plan.

Net open-market

−$6.48M

1 buy · 8 sales

Under a 10b5-1 plan

of the value sold

Insiders who bought / sold

1 / 5

executives and directors

Last open-market buy

Apr 2026

Apr 8, 2026

Get an email when HG's executives or directors buy, or make a large sale outside a plan.

Trades · last 2 years

Date	Insider	Trade	Shares	Price	Value	Of their stake	Filing
Sep 10 – 11	Timothy James Duffin Chief Underwriting Officer	SoldNo plan 2 parts	57,000	$34.61 average	$1.97M	23%	Form 4
Sep 3	David A Brown Director	SoldNo plan	50,000	$36.12	$1.81M	8.9%	Form 4
May 18	David A Brown Director	SoldNo plan	37,300	$32.16	$1.2M	6.2%	Form 4
May 15	David A Brown Director	SoldNo plan	12,700	$31.82	$404k	2.1%	Form 4
May 13	Jonathan B. Levenson Group Treasurer	SoldNo plan	6,075	$30.61	$186k	13%	Form 4
May 8	Jonathan B. Levenson Group Treasurer	SoldNo plan	3,030	$30.67	$93k	6.2%	Form 4
May 5	Brian John Deegan Group Chief Accounting Officer	SoldNo plan	11,000	$30.69	$338k	13%	Form 4
Apr 8	Bradley E Cooper Director	Bought	99	$31.01	$3k	New	Form 4
Nov 14, 2025	Alexander James Baker CEO, Hamilton Global Specialty	SoldNo plan	18,350	$26.19	$481k	18%	Form 4
Sep 5, 2025	Keith Donald Bernhard Group Chief Audit Officer	SoldNo plan	47,000	$24.37	$1.15M	47%	Form 4
Aug 15, 2025	Venkatanarayanan Krishnamoorthy Group CTO and Group CDO	SoldNo plan	18,988	$24.00	$456k	23%	Form 4
Aug 13, 2025	Alexander James Baker Chief Risk Officer	Sold10b5-1 plan	6,000	$23.79	$143k	4.9%	Form 4
Aug 13, 2025	Megan Jane Graves CEO, Hamilton Re	SoldNo plan	50,000	$23.75	$1.19M	32%	Form 4
Aug 12, 2025	Megan Jane Graves CEO, Hamilton Re	SoldNo plan	50,000	$23.27	$1.16M	24%	Form 4
Jun 2, 2025	Adrian Joseph Daws CEO, Hamilton Global Specialty	Sold10b5-1 plan	6,000	$22.00	$132k	3.1%	Form 4
May 19, 2025	Therese M Vaughan Director	Bought	4,750	$21.05	$100k	29%	Form 4
May 16, 2025	Megan Jane Thomas CEO, Hamilton Re	SoldNo plan	25,000	$21.02	$526k	11%	Form 4
Mar 19, 2025	Adrian Joseph Daws CEO, Hamilton Global Specialty	Sold10b5-1 plan	3,785	$21.00	$79k	1.9%	Form 4
Mar 14, 2025	Megan Jane Thomas CEO, Hamilton Re	Sold10b5-1 plan	53,256	$20.06	$1.07M	19%	Form 4
Mar 13, 2025	Keith Donald Bernhard Group Chief Audit Officer	SoldNo plan	15,000	$20.30	$305k	13%	Form 4
Mar 11, 2025	Adrian Joseph Daws CEO, Hamilton Global Specialty	Sold10b5-1 plan	139	$21.00	$3k	<0.1%	Form 4
Mar 7, 2025	Adrian Joseph Daws CEO, Hamilton Global Specialty	Sold10b5-1 plan	11,076	$20.69	$229k	5.2%	Form 4
Mar 5, 2025	Alexander James Baker Chief Risk Officer	Sold10b5-1 plan	6,000	—	—	4.7%	Form 4
Jan 21, 2025	Alexander James Baker Chief Risk Officer	Sold10b5-1 plan	4,000	—	—	4.7%	Form 4
Dec 26, 2024	Alexander James Baker Chief Risk Officer	Sold10b5-1 plan	4,000	—	—	4.8%	Form 4
Dec 13, 2024	Alexander James Baker Chief Risk Officer	Sold10b5-1 plan	4,000	—	—	4.6%	Form 4
Dec 12, 2024 – Dec 13, 2024	Venkatanarayanan Krishnamoorthy Group CTO and Group CDO	SoldNo plan 2 parts	11,842	—	—	29%	Form 4
Nov 25, 2024	Brian John Deegan Group Chief Accounting Officer	SoldNo plan	17,500	$19.18	$336k	46%	Form 4

Sep 10 – 11No plan
Timothy James Duffin
Chief Underwriting Officer · sold 57,000 at avg $34.61
$1.97M
23% of stake
Sep 3No plan
David A Brown
Director · sold 50,000 at $36.12
$1.81M
8.9% of stake
May 18No plan
David A Brown
Director · sold 37,300 at $32.16
$1.2M
6.2% of stake
May 15No plan
David A Brown
Director · sold 12,700 at $31.82
$404k
2.1% of stake
May 13No plan
Jonathan B. Levenson
Group Treasurer · sold 6,075 at $30.61
$186k
13% of stake
May 8No plan
Jonathan B. Levenson
Group Treasurer · sold 3,030 at $30.67
$93k
6.2% of stake
May 5No plan
Brian John Deegan
Group Chief Accounting Officer · sold 11,000 at $30.69
$338k
13% of stake
Apr 8
Bradley E Cooper
Director · bought 99 at $31.01
$3k
New position
Nov 14, 2025No plan
Alexander James Baker
CEO, Hamilton Global Specialty · sold 18,350 at $26.19
$481k
18% of stake
Sep 5, 2025No plan
Keith Donald Bernhard
Group Chief Audit Officer · sold 47,000 at $24.37
$1.15M
47% of stake
Aug 15, 2025No plan
Venkatanarayanan Krishnamoorthy
Group CTO and Group CDO · sold 18,988 at $24.00
$456k
23% of stake
Aug 13, 202510b5-1 plan
Alexander James Baker
Chief Risk Officer · sold 6,000 at $23.79
$143k
4.9% of stake
Aug 13, 2025No plan
Megan Jane Graves
CEO, Hamilton Re · sold 50,000 at $23.75
$1.19M
32% of stake
Aug 12, 2025No plan
Megan Jane Graves
CEO, Hamilton Re · sold 50,000 at $23.27
$1.16M
24% of stake
Jun 2, 202510b5-1 plan
Adrian Joseph Daws
CEO, Hamilton Global Specialty · sold 6,000 at $22.00
$132k
3.1% of stake
May 19, 2025
Therese M Vaughan
Director · bought 4,750 at $21.05
$100k
29% of stake
May 16, 2025No plan
Megan Jane Thomas
CEO, Hamilton Re · sold 25,000 at $21.02
$526k
11% of stake
Mar 19, 202510b5-1 plan
Adrian Joseph Daws
CEO, Hamilton Global Specialty · sold 3,785 at $21.00
$79k
1.9% of stake
Mar 14, 202510b5-1 plan
Megan Jane Thomas
CEO, Hamilton Re · sold 53,256 at $20.06
$1.07M
19% of stake
Mar 13, 2025No plan
Keith Donald Bernhard
Group Chief Audit Officer · sold 15,000 at $20.30
$305k
13% of stake
Mar 11, 202510b5-1 plan
Adrian Joseph Daws
CEO, Hamilton Global Specialty · sold 139 at $21.00
$3k
<0.1% of stake
Mar 7, 202510b5-1 plan
Adrian Joseph Daws
CEO, Hamilton Global Specialty · sold 11,076 at $20.69
$229k
5.2% of stake
Mar 5, 202510b5-1 plan
Alexander James Baker
Chief Risk Officer · sold 6,000
—
4.7% of stake
Jan 21, 202510b5-1 plan
Alexander James Baker
Chief Risk Officer · sold 4,000
—
4.7% of stake
Dec 26, 202410b5-1 plan
Alexander James Baker
Chief Risk Officer · sold 4,000
—
4.8% of stake
Dec 13, 202410b5-1 plan
Alexander James Baker
Chief Risk Officer · sold 4,000
—
4.6% of stake
Dec 12, 2024 – Dec 13, 2024No plan
Venkatanarayanan Krishnamoorthy
Group CTO and Group CDO · sold 11,842
—
29% of stake
Nov 25, 2024No plan
Brian John Deegan
Group Chief Accounting Officer · sold 17,500 at $19.18
$336k
46% of stake

How to read this. Insiders sell for many reasons: taxes, diversifying, a house. Open-market buys are rarer and say more. A 10b5-1 plan is a trading schedule set up months in advance, so those sales were not timed on news. Large holders (funds and 10% owners) are listed under Everything but not counted as insiders. If you own or watch HG, we send a push when an executive buys or makes a large sale outside a plan.

Source: SEC Form 4 filings, filed within two business days of each trade and checked for new ones every hour.

Related stocks: Fire, Marine & Casualty Insurance

AHL-PDAspen Insurance Holdings Ltd

SPNTSiriusPoint Ltd.

FIHLFidelis Insurance Holdings Limited

WTMWhite Mountains Insurance Group Ltd.

KNSLKinsale Capital Group Inc.

RLIRLI Corp.

HMNHorace Mann Educators Corp.

SKWDSkyward Specialty Insurance Group, Inc.

Spot a number that looks wrong? Check it in HG's SEC filings or

Download this analysis as a PDF (Pro)

Data sourced from SEC EDGAR filings and third-party price providers. Scores, valuations, and metrics are algorithmic estimates. This is not investment advice. See our Terms and Methodology.

2 of 2 free stocks used today

Keep analysing HG

Create a free account and get 14 days of Premium: every stock and every tool.

Unlimited stocksQuality, fair value and dividends for 10,000+ stocks
Stock screenerFilter on quality, valuation and dividend safety
Portfolio trackerReal return, dividend calendar and portfolio quality
Editable DCFChange the assumptions and watch fair value move
Compare side by sideUp to 10 stocks in one table
Unlimited alertsPrice, P/E, Quality Score and yield

No card. Moves to Free after, unless you upgrade.

Already have an account?

Or come back tomorrow. Stocks on your watchlist are always free to view.