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Matthew R Roberts

Associate at Skadden Arps Slate Meagher & Flom

Lawyer

New York

Deal Bio

Total Deals15

Valued Deals11

Total Value£ 14.29 B

Avg. Deal Size£ 1.30 B

Market Context

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11 Aug 2021|United States|Property and Casualty Insurance

Target: ROOT INC

Bidder: CARVANA

5 Service Providers

4 Target | 1 Bidder

20 Dealmakers

16 Target | 4 Bidder

£ 90 M

Value

25 Jul 2022|Bermuda|Insurance Brokers

Target: FIDELIS MANAGING GENERAL UNDERWRITER

Bidder: CAPITAL Z PARTNERS

16 Service Providers

1 Target | 8 Bidder | 7 Vendor

27 Dealmakers

3 Target | 15 Bidder | 10 Vendor

n/a

Value

08 Aug 2022|United States|Insurance Brokers

Target: AMERICAN RELIABLE INSURANCE COMPANY (FARM, RANCH, AND EQUINE BUSINESS)

Bidder: EVERETT CASH MUTUAL

7 Service Providers

3 Bidder | 4 Vendor

10 Dealmakers

2 Bidder | 8 Vendor

£ 70 M

Value

07 Oct 2022|United States|Full Line Insurance

Target: HALLMARK FINANCIAL SERVICES (EXCESS & SURPLUS LINES OPERATIONS)

Bidder: CORE SPECIALTY INSURANCE HOLDINGS

5 Service Providers

3 Bidder | 2 Vendor

17 Dealmakers

13 Bidder | 4 Vendor

£ 35 M

Value

15 Jun 2023|Spain|Full Line Insurance

Target: LIBERTY SEGUROS COMPANIA DE SEGUROS Y REASEGUROS SA

Bidder: ASSICURAZIONI GENERALI SPA

15 Service Providers

1 Target | 9 Bidder | 5 Vendor

53 Dealmakers

1 Target | 30 Bidder | 22 Vendor

£ 1.82 B

Value

01 Nov 2023|United States|Property and Casualty Insurance

Target: AMERICAN SURETY COMPANY

Bidder: CORE SPECIALTY INSURANCE HOLDINGS

5 Service Providers

3 Target | 2 Bidder

8 Dealmakers

1 Target | 7 Bidder

n/a

Value

03 Nov 2023|United States|Insurance Brokers

Target: CORVUS INSURANCE

Bidder: THE TRAVELERS COMPANIES INC

6 Service Providers

3 Target | 3 Bidder

34 Dealmakers

21 Target | 13 Bidder

£ 354 M

Value

01 Mar 2024|United States|Insurance Brokers

Target: AMERICAN NATIONAL (SPECIALTY MARKETS GROUP)

Bidder: CORE SPECIALTY INSURANCE HOLDINGS

4 Service Providers

2 Bidder | 2 Vendor

10 Dealmakers

1 Bidder | 9 Vendor

n/a

Value

26 Jun 2024|United Kingdom|Travel and Tourism

Target: AIG TRAVEL

Bidder: ZURICH INSURANCE GROUP

5 Service Providers

3 Bidder | 2 Vendor

13 Dealmakers

7 Bidder | 6 Vendor

£ 472 M

Value

26 Jun 2024|United States|Life Insurance

Target: AIG (GLOBAL PERSONAL TRAVEL INSURANCE BUSINESS)

Bidder: ZURICH INSURANCE LIMITED

6 Service Providers

4 Bidder | 2 Vendor

30 Dealmakers

23 Bidder | 7 Vendor

£ 473 M

Value

27 May 2025|Canada|Insurance Brokers

Target: TRAVELERS (CANADIAN PERSONAL INSURANCE BUSINESS)

Bidder: DEFINITY FINANCIAL CORPORATION

9 Service Providers

3 Bidder | 6 Vendor

67 Dealmakers

23 Bidder | 44 Vendor

£ 1.77 B

Value

10 Jun 2025|United States|Insurance Brokers

Target: ACCESSION RISK MANAGEMENT GROUP

Bidder: BROWN & BROWN INC

11 Service Providers

4 Target | 7 Bidder

45 Dealmakers

29 Target | 16 Bidder

£ 7.25 B

Value

07 Jul 2025|United States|Asset Managers and Custodians

Target: ELMTREE FUNDS

Bidder: BLACKROCK

9 Service Providers

3 Target | 6 Bidder

30 Dealmakers

14 Target | 16 Bidder

n/a

Value

07 Aug 2025|United States|Consumer Lending

Target: COMVEST CREDIT PARTNERS

Bidder: MANULIFE FINANCIAL CORPORATION

8 Service Providers

4 Target | 3 Bidder | 1 Vendor

20 Dealmakers

5 Target | 13 Bidder | 2 Vendor

£ 703 M

Value

18 Sep 2025|United Kingdom|Insurance Brokers

Target: INIGO LIMITED

Bidder: RADIAN GROUP

6 Service Providers

1 Target | 5 Bidder

17 Dealmakers

3 Target | 14 Bidder

£ 1.25 B

Value