#1Confidential bJ W. R. BERKLEY CORPORATION Investor Primer Year-End 2021 R#2Forward-Looking Information This is a "Safe Harbor" Statement under the Private Securities Litigation Reform Act of 1995. Any forward-looking statements contained herein, including statements related to our outlook for the industry and for our performance for the year 2021 and beyond, are based upon the Company's historical performance and on current plans, estimates and expectations. The inclusion of this forward-looking information should not be regarded as a representation by us or any other person that the future plans, estimates or expectations contemplated by us will be achieved. They are subject to various risks and uncertainties, including but not limited to: • the ongoing COVID-19 pandemic, including the related impact on the U.S. and global economies; • the cyclical nature of the property casualty industry; • • • the impact of significant competition, including new alternative entrants to the industry; the long-tail and potentially volatile nature of the insurance and reinsurance business; product demand and pricing; claims development and the process of estimating reserves; investment risks, including those of our portfolio of fixed maturity securities and investments in equity securities, including investments in financial institutions, municipal bonds, mortgage-backed securities, loans receivable, investment funds, including real estate, merger arbitrage, energy related and private equity investments; • the effects of emerging claim and coverage issues; • the uncertain nature of damage theories and loss amounts; natural and man-made catastrophic losses, including as a result of terrorist activities, epidemics or pandemics, such as COVID-19; • the impact of climate change, which may increase the frequency and severity of catastrophe events; • • • • • • general economic and market activities, including inflation, interest rates, and volatility in the credit and capital markets; the impact of the conditions in the financial markets and the global economy, and the potential effect of legislative, regulatory, accounting or other initiatives taken in response, on our results and financial condition; foreign currency and political risks (including those associated with the United Kingdom's withdrawal from the European Union, or "Brexit") relating to our international operations; our ability to attract and retain key personnel and qualified employees; continued availability of capital and financing; the success of our new ventures or acquisitions and the availability of other opportunities; Confidential • the availability of reinsurance; • our retention under the Terrorism Risk Insurance Program Reauthorization Act of 2019; • the ability or willingness of our reinsurers to pay reinsurance recoverables owed to us; • other legislative and regulatory developments, including those related to business practices in the insurance industry; • credit risk related to our policyholders, independent agents and brokers; • • the availability of dividends from our insurance company subsidiaries; • • • changes in the ratings assigned to us or our insurance company subsidiaries by rating agencies; potential difficulties with technology and/or cyber security issues; the effectiveness of our controls to ensure compliance with guidelines, policies and legal and regulatory standards; and other risks detailed from time to time in the Company's filings with the U.S. Securities and Exchange Commission. These risks and uncertainties could cause our actual results for the year 2021 and beyond to differ materially from those expressed in any forward- looking statement we make. Any projections of growth in our revenues would not necessarily result in commensurate levels of earnings. Forward- looking statements speak only as of the date on which they are made, and the Company undertakes no obligation to update publicly or revise any forward-looking statement, whether as a result of new information, future developments or otherwise.#3LONG-TERM STRATEGY REMAINS CONSTANT Confidential Superior Risk Adjusted Underwriting Results Superior Long-Term Risk-Adjusted Return on Equity and Shareholder Value Creation Above Market Risk-Adjusted Investment Returns Prudent Capital Management Decentralized operating units • Specialized expertise • Close to the customer •Cycle management • Exposure and volatility management • Create new businesses with the right talent •High-quality fixed income portfolio ⚫ Duration management •Individual asset class expertise • Invest for total return while always being conscious of risk •Maintain optimal capital •Optimize capital structure • Allocate capital on a risk-adjusted basis 3#4STRATEGY FOR OPTIMIZING RISK-ADJUSTED RETURN AND LONG- TERM SHAREHOLDER VALUE CREATION OPERATE WHERE KNOWLEDGE IS A COMPETITIVE ADVANTAGE ☐ Primarily commercial lines including excess and surplus lines, admitted lines and specialty 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 ☐ Seek to avoid unfavorable (unpredictable) political or legal environments Long-term ROE target = 15%#5UNIQUE ADVANTAGES AS DECENTRALIZED SPECIALIST UNDERWRITER • • • • • • 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#6TOP TIER RETURN TO SHAREHOLDERS 18.00% RETURN ON EQUITY 16.00% 14.00% 45.00% 12.00% TOTAL SHAREHOLDER RETURN* 40.00% 10.00% 35.00% 8.00% 6.00% 4.00% 2.00% 0.00% 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 30.00% 25.00% 20.00% 15.00% 10.00% 5.00% 0.00% -5.00% 2010 2011 2012 2013 2014 2015 2016 2017 2018 *Annual growth in stock price plus dividends 2019 2020 2021#7W. R. BERKLEY CORPORATION OVERVIEW NET INCOME NET PREMIUMS WRITTEN $ in millions $1,200 $ in millions $10,000 $1,000 $9,000 $800 $8,000 $7,000 $600 $6,000 $400 $5,000 $4,000 $200 $3,000 $2,000 $1,000 $0 2012 2013 2014 2015 2016 2017 2018 $0 2019 2020 2021 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021#8REPORTING IN TWO SEGMENTS OF THE GLOBAL NON-LIFE MARKET 2021 INSURANCE NET PREMIUMS WRITTEN $7.7 BILLION 2021 REINSURANCE & MONOLINE EXCESS NET PREMIUMS WRITTEN $1.1 BILLION Worker's Comp, 15% Short-Tail Lines, 19% Other Liability, 37% Prof. Liability, 14% Commercial Auto, 14% Casualty 65% Property 16% Monoline Excess 19%#9OPERATING THROUGH 56 INDEPENDENTLY MANAGED UNITS 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 REGIONAL PRODUCT SPECIALTY INDUSTRY SPECIALTY REINSURANCE Focused on customers with complex and diverse risks Variety of products distributed to regionally differentiated customers Specialized products for specific lines of insurance Offers coverages tailored to industries with unique exposures A full range of products available globally INTERNATIONAL Focused range of products with local expertise in select non-US markets Admiral Insurance Acadia Berkley Custom Berkley Aspire Berkley Mid-Atlantic Berkley North Pacific Berkley A&H Berkley Cyber Risk Solutions Key Risk Berkley Agribusiness Berkley Luxury Group Berkley Re America Berkley Canada Midwest Employers Berkley Fire & Marine Preferred Employers Berkley Alliance Berkley Asset Protection Berkley Offshore Berkley Re Asia Pacific Berkley Oil & Gas Berkley Re Solutions Berkley Insurance Asia Berkley Insurance Australia Berkley Global Nautilus Berkley Southeast Product Recall Vela Continental Western Berkley Management Berkley Construction Professional Berkley Entertainment & Berkley One Berkley Re UK Berkley International Latinoamerica Protection Berkley Program Specialists W. R. Berkley Europe Confidential Sports Verus Union Standard BerkleyNet Berkley Pro Berkley Select Berkley Small Business Solutions Berkley Surety Gemini Berkley Environmental Berkley Financial Specialists Berkley Healthcare Berkley Human Services Berkley Industrial Comp Berkley Life Sciences Berkley Public Entity Berkley Risk Berkley Technology Carolina Casualty W/R/B Underwriting 9#10MANAGING THE INSURANCE CYCLE IS CRITICAL TO LONG-TERM SUCCESS Confidential WRB: Write as much good business as possible WRB: Accelerate growth as price adequacy returns Price Increases High Profitability to various market segments WRB: Capitalize on market Capacity Withdrawal/ Reduced Competition WRB: Slower growth and more selective underwriting Increased Capital Needs a Return + New capacity = Increased competition WRB: Focus on retention; maintain disciplined underwriting dislocations Create new units/divisions to Low Profitability Price Reductions position for market turn WRB: Be willing to sacrifice volume for profitability 10 10#11Year-Over-Year % Change in NPW Q2:05 Confidential YOY Change NPW Note: Quarterly rate changes exclude Treaty Reinsurance NPW growth in 2016 distorted by structured reinsurance treaties. Q4:05 Q2:06 Q4:06 Q2:07 Q4:07 Q2:08 Q4:08 Q2:09 Q4:09 Q2:10 Q4:10 Q2:11 Q4:11 Q2:12 Q4:12 Q2:13 Q4:13 YOY Written Price Change Q2:14 MANAGING THE INSURANCE CYCLE IS CRITICAL TO LONG-TERM SUCCESS Q4:14 Q2:15 Q4:15 Q2:16 Q4:16 Q2:17 Q4:17 Q2:18 Q4:18 Q2:19 Q4:19 Q2:20 Q4:20 Q2:21 Q4:21 YOY Earned Price Change 11 Year-Over-Year % Price Change#12SIGNIFICANTLY LESS VOLATILITY FROM CATASTROPHES Confidential (Percent) RATIO OF EVENT LOSS TO SURPLUS FOR LARGEST EVENTS SINCE 1992* 18% 16.2% 16.4% 16% 13.8% 14% 10.9% 11.4% 12% 9.6% 10% 6.9% 8% 6% 4.3% 4.3% 4.6% 3.9% 4% 2.4% 3.0% 1.7% 2.8% 1.9% 1.1% 0.9% 0.9% 0.8% 2% 0.0% 0.6% 0% 6/30/1992 12/31/1993 6/30/2001 6/30/2005 Hurricane Northridge Sept. 11 Hurricane Andrew Earthquake Katrina Attacks Financial 3/31/2011 9/30/2012 6/30/2017 Crisis as of 2Q11 Storms Storm Sandy 3Q2017 4Q2018 3/31/2009(1) Events Events 9/30/2018 12/31/2019 6/30/2021 COVID-19 Hurricane Ida 2020 (2) (3) Industry Event Loss/Surplus WRB Event Loss/Surplus * Ratio is for end-of-quarter surplus immediately prior to event. (1) Change in surplus from 12/31/2007 peak to date of maximum capital erosion at 3/31/09. Reflects losses offset by earnings. (2) Lloyd's estimate > $114mm (3) RMS estimate $31-44B Sources: PCS; Insurance Information Institute; A.M. Best; WRB bJ 8 12#13Confidential LACK OF VOLATILITY DEMONSTRATED IN OUR RESULTS 90.0% 80.0% 70.0% 60.0% 50.0% 40.0% 30.0% 20.0% 10.0% 0.0% 2007 Accident year loss ratios consistently outperform... 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 20% 18% 16% 14% 12% 10% 8% 6% 4% 2% 0% 2001 2003 2002 ... . With predictably less impact from catastrophes PC Industry WRB PC Industry Points of Cat WRB Points of Cat Source: S&P Global Insights; A.M. Best; WRB Note: 2021 Industry data not yet available *PC Industry through 9 months 2021 Note: Does not include losses associated with COVID-19 2018 2019 2020 2021* 13#14INVESTING FOR THE FUTURE - START UPS NPW ($000) $150,000 Example of a Start Up Based on Actual Results $100,000 $50,000 $0 -$50,000 NUI ($000) $30,000 $25,000 $20,000 $15,000 $10,000 $5,000 T $0 -$5,000 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 Net premiums written -Net Underwriting Income#15ASSET ALLOCATION AT DECEMBER 31, 2021 Duration - 2.4 years; Average quality - AA- CATEGORY Fixed-maturity securities U.S. government State and municipal Mortgage-backed securities Asset-backed securities Corporate bonds Foreign government CARRYING VALUE ($MM) % TOTAL 855.3 3.6% 3,373.3 14.2% 1,072.9 4.5% 4,490.6 18.9% 5,595.7 23.6% 1,214.9 5.1% Total fixed-maturity securities $ 6,602,673 69.9% Equities 941.2 4.0% Real estate Investment funds Cash and cash equivalents Arbitrage trading account Loans receivable Total 1,852.5 7.8% 1,480.6 6.2% 1,568.8 6.6% 1,179.6 5.0% 115.2 0.1% $ 23,740.7 100.0%#16GROSS INVESTMENT INCOME $ in millions $800 $700 $600 $500 $400 $300 $200 $100 $0 Average Annualized Yield Fixed Maturity Non-Fixed Maturity 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 on Fixed Maturity 3.7% 3.5% 3.4% 3.2% 3.2% 3.4% 3.6% 3.4% 2.7% 2.2% Total Average Annualized yield 4.1% 3.7% 3.9% 3.3% 3.4% 3.3% 3.7% 3.4% 3.0% 3.1%#17NET REALIZED GAINS ON INVESTMENT SALES Confidential 18.0% Realized gains have contributed an average of 2.5% to our ROE over the past several years 16.2% 16.0% 15.0% 1.1% 14.0% 12.9% 15.1% 13.1% 12.5% 3.8% 11.6% 11.8% 12.0% 11.0% 10.9% 1.7% 3.3% 3.8% 1.8% 11.2% 2.0% 10.0% 1.8% 10.8% 8.7% 9.6% 9.8% 4.2% 9.7% 9.2% 9.3% 8.0% 1.5% 7.2% 6.0% 6.7% 4.0% 2.0% 0.0% 2012 2013 2014 2015 2016 2017 2018* 2019* 2020* 2021* Operating ROE (Including OTTI) ROE From Net Realized and Unrealized Gains Before OTTI *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 since 2018 due to the adoption of ASU 2016-01 on January 1, 2018. 17#188% 7% 6% 5% 4% 3% 2% 1% 0% -1% -2% 2Q 06 4Q 06 2Q 07 4Q 07 2Q 08 4Q 08 2Q 09 4Q 09 2Q 10 4Q 10 2Q 11 4Q 11 2Q 12 SIXTY QUARTERS OF FAVORABLE RESERVE DEVELOPMENT Confidential Reserve Development Favorable / (Unfavorable) ―% of Earned Premium 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%. 4Q 12 2Q 13 4Q13 2Q14 Quarterly Reserve Development $ Millions $80 $70 $60 $50 $40 $30 $20 $10 $0 -$10 -$20 4Q14 2Q15 4Q15 2Q16 4Q16 2Q17 4Q17 2Q18 4Q18 2Q19 στον 18 2Q20 4Q20 2Q21 4Q21#19CAPITAL STRUCTURE & DEBT MATURITY PROFILE December 31, 2021 December 31, Capital Profile 2020 ($ millions) Senior notes and other debt $ 2,259 $ 1,623 Subordinated debentures 1,008 1,102 Total debt 3,267 2,725 Common equity 6,653 6,311 Total capitalization $ 9,920 $ 9,036 Debt-to-capital ratio 32.9% 30.2% Proforma for 1Q22 Maturities 29.9% Debt Maturities $700 $600 $470 $500 $427 $400 $400 $350 $300 $250 $200 $100 آلات $185 $300 $250 $650 2022* 2037 2044 2050 2052 2058 2059 2060 2061 Confidential *$76M repaidat maturity on January 3, 2022 Actively manage capital Hybrids add permanence to capital structure Well-balanced debt maturity profile Significant off-balance sheet value remains in various private equity and real estate investments Capital Transactions ▪ Issued subordinated debt in February 2021 ($300M @ 4.125%) Redeemed subordinated debt in March 2021 ($110M @ 5.9%) Issued senior debt in March 2021 ($400M @ 3.55%) Redeemed subordinated debt in June 2021 ($290M @ 5.75%) ■Issued senior debt in September 2021 ($350M @ 3.15%) to partially prefund 2022 maturities Repurchased 1.8M shares for $122M in 2021 ■ 10M shares remain under share repurchase authorization as of 12/31/21 Liquidity Strong liquidity throughout the Group (approx. $1.5 bn) Meaningful growth in operating cash flow ($2.2 bn in 2021) 19#20EXCESS CAPITAL RETURNED TO SHAREHOLDERS ■Net Income Dividends & Share Repurchases $1,200 $1,000 $800 $600 $400 $200 $0 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 10.7% 64.5% 208.6% 59.3% 109.5% 51.2% 61.0% 43.8% 64.8% 55.9% 52.6% 43.0% 43.5% 47.8% 81.1% 46.8% Dividends and shares repurchased as a percent of net income SINCE 1/1/2006, WRB HAS RETURNED $5.3 BILLION (66% OF NET INCOME) TO SHAREHOLDERS THROUGH DIVIDENDS AND SHARE REPURCHASES OR 132% OF 12/31/2005 MARKET CAPITALIZATION#21GROWTH IN DIVIDENDS PER SHARE ■Regular Cash Dividends Special Dividends $1.60 $1.40 $1.20 $1.00 $0.80 11.0% CAGR in regular cash dividends $0.60 $0.40 $0.20 $0.00 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 WRB HAS PAID CASH DIVIDENDS WITHOUT INTERRUPTION SINCE 1976#2290,000% 80,000% 70,000% W. R. BERKLEY CORPORATION'S PERFORMACE VS. THE S&P 500' OVERALL GAIN IN BOOK VALUE PER SHARE WITH DIVIDENDS COMPOUNDED 1973 - 2021 60,000% 50,000% 40,000% 30,000% 20,000% 10,000% % 1974 1975 1976 1977 1978 1979 1980 1981 1982 1983 1984 1985 1986 1987 1988 1989 1990 1991 1992 1993 1994 1995 1996 1997 1998 WRB S&P 500 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. 1999 2000 2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 15,925% 87,869%#23bd R Thank You. > Karen Horvath 203 629 3040 ☑ [email protected] www.berkley.com Confidential "Always do right. This will gratify some people, and astonish the rest." - Mark Twain - 23