W R Berkley : 2021 Proxy Statement

W. R. BERKLEY CORPORATION

Notice of 2021 Annual Meeting of Stockholders

and Proxy Statement

W. R. BERKLEY CORPORATION

475 Steamboat Road

Greenwich, Connecticut 06830

Tel: [phone] • www.berkley.com

To our fellow shareholders:

Your vote is important to us, and on behalf of our Board of Directors, we encourage you to cast your ballot on the items discussed in the Proxy Statement using the attached proxy card or by voting via telephone or online.

While 2020 was a year like no other, it was another year of strong performance by our Company in many ways. Our focus on risk-adjusted return continued, but our efforts for much of the year centered on issues surrounding the COVID-19 pandemic and its economic impact. These events affected our employees, customers and communities alike. Our employees demonstrated incredible professional and personal resiliency and continued to support the communities where we live and work by volunteering their time and skills and contributing to worthy causes. Amidst it all, we responsibly grew our business while rewarding shareholders with 10.5% growth in book value per share before share repurchases and dividends. We are proud of not only what we achieved, but also how we accomplished it.

We were able to produce these results because W. R. Berkley Corporation is a company with a long-term perspective, a commitment to managing the insurance cycle and an acute awareness of the potential impact of unforeseen risks. This focus comes about because together, our Board of Directors and our employees are the Company's largest shareholders and have been for many years.

We actively consider environmental, social and governance (ESG) matters, including the impact of climate change, the need for diversity and inclusion, and the importance of our employee's professional growth through education and training. Understanding of and sensitivity to these issues makes our business and our communities better for all our stakeholders. We continue to invest heavily in developing the behaviors and processes that foster innovation at all levels of our organization to enhance our value to our clients and customers and to prepare our employees for the future.

As we look forward to the remainder of 2021 and beyond, we are optimistic about every aspect of our enterprise. Our Company is built to succeed in periods of uncertainty through a constant evaluation of risk and reward in all aspects of our business, and to excel in all phases of market activity. We are well positioned for the current improving economic times.

Direct communication with our independent shareholders remains extremely strong and we look forward to continuing this important dialogue with you, our fellow owners. The resiliency, courage and commitment of our people continue to inspire us, and we thank them for their constant efforts. Their dedication to our values will allow us the opportunity to continue delivering superior risk-adjusted returns and growth in shareholder value in a manner that we can all be proud of for years to come.

Sincerely,

William R. Berkley	W. Robert Berkley, Jr.
Executive Chairman	President and Chief Executive Officer
	"Always do right. This will gratify some people and astonish the rest."

- Mark Twain

W. R. BERKLEY CORPORATION

475 Steamboat Road

Greenwich, Connecticut 06830

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

June 15, 2021

NOTICE IS HEREBY GIVEN that the Annual Meeting of Stockholders (the "Annual Meeting") of W. R. Berkley Corporation (the "Company") will be held online through an audio-only webcast at www.virtualshareholdermeeting.com/WRB2021 on Tuesday, June 15, 2021 at 1:30 p.m. for the following purposes:

1. To elect as directors to serve until their successors are duly elected and qualified the five nominees named in the accompanying proxy statement;
2. To approve an increase in the number of shares reserved under the W. R. Berkley Corporation 2009 Directors Stock Plan (as amended and restated, the "Directors Stock Plan");
3. To consider and cast a non-binding advisory vote on a resolution approving the compensation of the Company's named executive officers pursuant to the compensation disclosure rules of the U.S. Securities and Exchange Commission, or "say-on-pay" vote;
4. To ratify the appointment of KPMG LLP as the independent registered public accounting firm for the Company for the fiscal year ending December 31, 2021; and
5. To consider and act upon any other matters which may properly come before the Annual Meeting or any adjournment thereof.

In accordance with the Company's By-Laws, the Company's Board of Directors has fixed the close of business on April 19, 2021 as the date for determining stockholders of record entitled to receive notice of, and to vote at, the Annual Meeting.

Due to COVID-19-related public health restrictions and for the safety and well-being of our stockholders, the Annual Meeting will be conducted online through an audio-only webcast at www.virtualshareholdermeeting.com/WRB2021. The accompanying Proxy Statement contains information about participating in the Annual Meeting. There will be no physical location for the Annual Meeting. As always, we encourage you to vote your shares prior to the Annual Meeting.

By Order of the Board of Directors,

PHILIP S. WELT

Executive Vice President - General Counsel and

Secretary

Dated: April 27, 2021