LONG-TERM STRATEGY

Superior Risk Adjusted Underwriting Results

• Decentralized operating units

• Specialized expertise

• Close to the customer

• Cycle management

• Exposure and volatility management

• Create new businesses with the right talent

Above Market Risk-Adjusted Investment Returns

• High-quality fixed income portfolio

• Duration management

• Individual asset class expertise

• Invest for capital gains as well as income

Prudent Capital Management

• Maintain optimal capital

• Optimize capital structure

• Allocate capital on a risk-adjusted basis

2

Superior Long-Term

Risk-Adjusted Return on Equity

and Shareholder Value Creation

STRATEGY FOR OPTIMIZING RISK-ADJUSTED RETURN AND

LONG-TERM SHAREHOLDER VALUE CREATION

OPERATE WHERE KNOWLEDGE IS A COMPETITIVE ADVANTAGE

Primarily commercial lines: Recently introduced high-net-worth personal lines

Niche player with specialized market knowledge and presence

Emphasize industries and economies with strong margins

Expand selectively in attractive global markets

AVOID UNREWARDED VOLATILITY

Focus on products with low individual policy limits

Issue policies with defined aggregate limits

Avoid unfavorable (unpredictable) political or legal environments

3Long-term ROE target = 15%

Decentralized structure allows us to react quickly to changing market conditions

Specialized knowledge is competitive advantage for independently-managed niche businesses

Business profile and a constant concern for unforeseen risks limit earnings volatility

Conservatively managed balance sheet limits volatility in shareholders’ equity

Meaningful employee ownership promotes long-term perspective

Strategic cycle management and critical capital management enable well-timed growth

Success in development of new businesses offers optimal value creation, notwithstanding cycles

4

UNIQUE ADVANTAGES AS DECENTRALIZED SPECIALIST UNDERWRITER

TOP TIER RETURN TO SHAREHOLDERS

0.00%

2.00%

4.00%

6.00%

8.00%

10.00%

12.00%

14.00%

16.00%

RETURN ON EQUITY

5

0.00%

5.00%

10.00%

15.00%

20.00%

25.00%

30.00%

TOTAL SHAREHOLDER RETURN*

*Annual growth in stock price plus dividends

W. R. BERKLEY CORPORATION OVERVIEW

$0

$1,000

$2,000

$3,000

$4,000

$5,000

$6,000

$7,000

NET PREMIUMS WRITTEN

6

$0

$100

$200

$300

$400

$500

$600

$700

NET INCOME

$ in millions $ in millions

Casualty67%

Property33%

Workers' Comp26%

Other Liability

32% Short-Tail Lines20%

Comm'l Auto11%

Prof. Liability

10%

REPORTING IN TWO SEGMENTS OF THE GLOBAL NON-LIFE MARKET

2017 REINSURANCE NET PREMIUMS WRITTEN$544 MILLION

2017 INSURANCE NET PREMIUMS WRITTEN$5.7 BILLION

7

Berkley is comprised of individual operating units that serve distinct markets requiring specialized

knowledge of a particular territory, market segment, product or type of business

E&S Focused on customers with complex and diverse risks

REGIONALVariety of products distributed to regionally differentiated

customers

PRODUCTSPECIALTYSpecialized products for specific lines of insurance

INDUSTRY SPECIALTYOffers coverages tailored to industries with

unique exposures

REINSURANCEA full range of products

available globally

INTERNATIONALFocused range of products with local expertise in select

non-US markets

Admiral Insurance Acadia Berkley A&H American Mining Berkley Offshore Berkley Re America Berkley Canada

Berkley CustomBerkley Mid-

Atlantic

Berkley Cyber Risk

Solutions

Berkley

Agribusiness

Berkley Oil &

GasBerkley Re Asia Pacific Berkley Insurance Asia

Berkley AspireBerkley North

Pacific

Berkley Fire &

MarineBerkley Alliance

Berkley OneBerkley Re Solutions

Berkley Insurance

Australia

Nautilus Berkley SoutheastBerkley Global

Product Recall

Berkley Asset

Protection

Berkley Program

SpecialistsBerkley Re UK

Berkley International

Latinoamerica

Vela Continental Western BerkleyNet

Berkley

Entertainment &

Sports

Berkley Public

EntityW. R. Berkley Europe

Verus Union Standard Berkley ProBerkley

Environmental

Berkley RiskW/R/B Underwriting

Berkley Select Berkley FinSecureBerkley

Technology

Berkley Surety Berkley Healthcare Carolina Casualty

GeminiBerkley Human

Services

Key RiskBerkley Life

Sciences

Midwest EmployersBerkley Luxury

Group

Preferred Employers BerkleyMed

OPERATING THROUGH 53 INDEPENDENTLY MANAGED UNITS

8

High Profitability

Increased CapitalNeeds a Return +New capacity =

Increased competition

PriceReductions

Low Profitability

Capacity Withdrawal

Reduced Competition

Price Increases

MANAGING THE INSURANCE CYCLE IS CRITICAL TO LONG-TERM SUCCESS

9

WRB: Write as much good business as possible

WRB: Be willing to sacrifice volume for profitability

WRB: Focus on

retention;

maintain

disciplined

underwriting

WRB: Slower

growth and

more selective

underwriting

WRB: Capitalize on

market dislocations

Create new

units/divisions to

position for market

turn

WRB: Accelerate

growth as price

adequacy returns

to various market

segments

Note: Quarterly rate changes exclude Treaty Reinsurance

NPW growth in 2016 distorted by structured reinsurance treaties.

MANAGING THE INSURANCE CYCLE IS CRITICAL TO LONG-TERM SUCCESS

10

Q1:0

5

Q3:0

5

Q1:0

6

Q3:0

6

Q1:0

7

Q3:0

7

Q1:0

8

Q3:0

8

Q1:0

9

Q3:0

9

Q1:1

0

Q3:1

0

Q1:1

1

Q3:1

1

Q1:1

2

Q3:1

2

Q1:1

3

Q3:1

3

Q1:1

4

Q3:1

4

Q1:1

5

Q3:1

5

Q1:1

6

Q3:1

6

Q1:1

7

Q3:1

7

Q1:1

8

Q3:1

8

Yea

r-O

ver-

Yea

r %

Pri

ce C

han

ge

Yea

r-O

ver-

Yea

r %

Ch

ange

in N

PW

YOY Change NPW YOY Written Price Change YOY Earned Price Change

9.6%

6.9%

10.9%

13.8%

16.2%

3.0%4.3%

11.4%

4.3%

1.1%2.4%

0.9%0.0%

1.7% 0.9%1.9%

0%2%4%6%8%

10%12%14%16%18%

6/30/1992HurricaneAndrew

12/31/1993NorthridgeEarthquake

6/30/2001Sept. 11Attacks

6/30/2005HurricaneKatrina

Financial Crisisas of

3/31/2009**

3/31/20112Q11 Storms

9/30/2012Storm Sandy

3Q2017Events***

Industry Event Loss/Surplus WRB Event Loss/Surplus

SIGNIFICANTLY LESS VOLATILITY FROM CASTSTROPHES

11

RATIO OF EVENT LOSS TO SURPLUS FOR LARGEST EVENTS SINCE 1992*

*** Ratio is for end-of-quarter surplus immediately prior to event.

*** Change in surplus from 12/31/2007 peak to date of maximum capital erosion at 3/31/09. Reflects losses offset by earnings.

*** Assumes $10B in losses from Hurricane Michael

Sources: PCS; Insurance Information Institute; A.M. Best; WRB

(Percent)

12

0%

2%

4%

6%

8%

10%

12%

14%

16%

18%

20%

. . . With predictably less impact from catastrophes

PC Industry Points of cat WRB Points of Cat

Sources: SNL, A.M. Best, WRB

0%

10%

20%

30%

40%

50%

60%

70%

80%

90%

20072008200920102011201220132014201520162017

Accident year loss ratios consistently outperform . . .

WRB PC Industry

LACK OF VOLATILITY DEMONSTRATED IN OUR RESULTS

60.0

61.0

62.0

63.0

64.0

65.0

66.0

67.0

68.0

10 YearAverage

7 YearAverage

5 YearAverage

3 YearAverage

As of December 31, 2017

13

Reported Accident Year Loss Ratio Averages

LOW EXPOSURE PROFILE IS CLEARLY DEMONSTRATED IN ACTIVE PERIODS

Our outperformance appeared to have declined in the 5 year period ended 2017, as catastrophe activity

was benign from 2013 to 2015. However, a return to normalized catastrophe losses in 2016 and a record

level of catastrophe losses in 2017 demonstrated that the performance gap remains, a tribute to our

disciplined underwriting and risk management.

$-

$40

$80

$120

$160

$ Billions

U.S. Insured Cat Losses(2015 Dollars)

Sources: Property Claims Service/ISO; Insurance Information

Institute; Munich Re

Highly rated peers include ACGL, AFG, AGII, AWH, CAN, CB, CINF,

ENH, HIG, LIBERTY MUTUAL, MKL, NAV, RE RLI, THG, TRV,

XL, Y

Investing for the Future – Start Ups

14

-$10,000

$0

$10,000

$20,000

$30,000

$40,000

$50,000

$60,000

$70,000

-$50,000

$0

$50,000

$100,000

$150,000

$200,000

$250,000

$300,000

NUI ($000)NPW ($000)

Example of a Start UpBased on Actual Results

Net premiums written Net Underwriting Income

15

Dual objective of preserving principal

& optimizing return

Managed for the long term; not trading

oriented

Most investments managed in house

Currently maintaining a defensive

position in fixed income markets

Shorter duration – 2.9 years

Maintain quality – AA-

Interest rate risk minimized by

matching assets/liabilities duration

within 1 year

CATEGORY

CARRYING

VALUE

($MM) % TOTAL

Fixed-maturity securities

U.S. government 487.0 2.6%

State and municipal 4,085.4 21.8%

Mortgage-backed securities 1,559.5 8.3%

Asset-backed securities 2,549.9 13.6%

Corporate bonds 4,065.2 21.7%

Foreign government 825.4 4.4%

Total fixed-maturity securities $ 13,572.4 72.4%

Equities 325.3 1.8%

Real estate 1,917.3 10.2%

Investment funds 1,250.4 6.7%

Cash and cash equivalents 876.9 4.7%

Arbitrage trading account 678.3 3.6%

Loans receivable 96.6 0.6%

Total $ 18,717.2 100.0%

ASSET ALLOCATION AT SEPTEMBER 30, 2018

GROSS INVESTMENT INCOME

16

$0

$100

$200

$300

$400

$500

$600

$700

2012 2013 2014 2015 2016 2017 YTD9/30/2017

YTD9/30/2018

$ in millions

Fixed Maturity Non-Fixed Maturity

Average Annualized

Yield on Fixed Maturity 3.7% 3.5% 3.4% 3.2% 3.2% 3.4% 3.3% 3.6%

Total Average

Annualized yield 4.1% 3.7% 3.9% 3.3% 3.4% 3.3% 3.3% 3.8%

NET REALIZED GAINS ON INVESTMENT SALES

17

9.6% 9.9%

11.1%

9.2% 9.3%

6.7%

10.1%

3.3%1.8%

3.8%

1.8%

4.0%

4.2%

2.4%

0.0%

2.0%

4.0%

6.0%

8.0%

10.0%

12.0%

14.0%

16.0%

2012 2013 2014 2015 2016 2017 YTD 2018*

Operating ROE (Including OTTI) ROE From Realized Gains on Investment Sales

12.9%

15.0%

11.0%

13.3%

Realized gains have contributed an average of more than 3% to our ROE over the past several years

11.6%

10.9%

12.5%

*Total ROE and ROE from realized gains on investment sales are reduced by the inclusion of change in unrealized gains

on equity securities within net income in 2018 due to the adoption of ASU 2016-01 on January 1.

-$20

-$10

$0

$10

$20

$30

$40

$50

$60

$70

$80

-2%

-1%

0%

1%

2%

3%

4%

5%

6%

7%

8%

1Q

06

3Q

06

1Q

07

3Q

07

1Q

08

3Q

08

1Q

09

3Q

09

1Q

10

3Q

10

1Q

11

3Q

11

1Q

12

3Q

12

1Q

13

3Q

13

1Q

14

3Q

14

1Q

15

3Q

15

1Q

16

3Q

16

1Q

17

3Q

17

1Q

18

3Q

18

Quarterly Reserve Development

Reserve Development Favorable / (Unfavorable) % of Earned Premium

FORTY-SEVEN QUARTERS FAVORABLE RESERVE DEVELOPMENT

18

$ Millions

1Q17 Includes an increase to prior year reserves of $30 million, before tax, or $22 million after tax related to the Ogden rate change.

The Ogden rate is the discount rate used to calculate lump-sum bodily injury payouts in the U.K. and was recently reduced by the

U.K. Ministry of Justice from +2.5% to -0.75%.

CAPITAL STRUCTURE & DEBT MATURITY PROFILE

21

Actively manage capital

Hybrids add permanence to capital

structure

Well-balanced debt maturity profile

9.17 million shares remain under share

repurchase authorization as of 9/30/18

Two $0.50 Special Dividends in 2018

Realized $336 million in gains in 2017 and

$421 million YTD through 9/30/2018

Significant off-balance sheet value in

various private equity and real estate

investments

September 30,

2018

December 31,

2017

($ millions)

Senior notes and other debt $ 1,791 $ 1,769

Subordinated debentures 907 728

Total debt 2,698 2,497

Common equity 5,479 5,411

Total capitalization $ 8,177 $ 7,909

Debt-to-capital ratio 33.0% 31.6%

$450

$300

$427

$250

$350 $350

$400

$185

$-

$50

$100

$150

$200

$250

$300

$350

$400

$450

$500

2019 2020 2022 2037 2044 2053 2056 2058

Debt Maturities

GROWTH IN BOOK VALUE PER SHARE

20

$0.00

$10.00

$20.00

$30.00

$40.00

$50.00

$60.00

$70.00

BOOK VALUE PER SHARE PLUS CUMULATIVE DIVIDENDS AND SHARE REPURCHASE

EXCESS CAPITAL RETURNED TO SHAREHOLDERS

21

$0

$100

$200

$300

$400

$500

$600

$700

$800

$900

Net Income Dividends & Share Repurchases

10.7% 64.5% 208.6% 59.3% 109.5% 51.2% 61.0% 43.8% 64.8% 55.9% 52.6% 43.0% 34.9% 35.8%

Dividends and shares repurchased as a percent of net income

SINCE 1/1/2006, WRB HAS RETURNED $4.0 BILLION (59% OF NET INCOME) TO SHAREHOLDERS THROUGH DIVIDENDS AND SHARE REPURCHASES OR 99% OF MARKET CAPITALIZATION AS

OF 12/31/2005

$0.00

$0.20

$0.40

$0.60

$0.80

$1.00

$1.20

Regular Cash Dividends Special Dividends

GROWTH IN DIVIDENDS PER SHARE

22WRB HAS PAID CASH DIVIDENDS WITHOUT INTERRUPTION SINCE 1976

W. R. BERKLEY CORPORATION’S PERFORMACE VS. THE S&P 500®

23

65,513%

Note: W. R. Berkley Corporation’s book value per share has been adjusted for stock dividends paid from 1975 to 1983. Stock dividends were 6% in each year from 1975 to 1978, 14% in 1979, and 7% in each year from 1980 to 1983. The Company has paid cash dividends each year since 1976

OVERALL GAIN IN BOOK VALUE PER SHARE WITH DIVIDENDS COMPOUNDED

1973-SEPTEMBER 30, 2018

-5,000%

5,000%

15,000%

25,000%

35,000%

45,000%

55,000%

65,000%1

97

3

19

75

19

77

19

79

19

81

19

83

19

85

19

87

19

89

19

91

19

93

19

95

19

97

19

99

20

01

20

03

20

05

20

07

20

09

20

11

20

13

20

15

20

17

WRB S&P 500

9,698%

Sep

tem

ber

30,

2018

“Always do right. This will gratify some people,

and astonish the rest.” - Mark Twain -