2020Annual ReportCNA Financial Corporation

Faced with unprecedented challenges in 2020, CNA demonstrated flexibility andresilience as we continued to move forward – strengthening our market visibility,increasing our specialization and deepening our industry partnerships. With a steadfast focus on technology, analytics and collaborative global underwriting, we continue to provide the deep expertise and customized solutions our agents, brokers and policyholders expect.

2020 Financial Highlights

$12.7B

$8.1BNet Written Premium

$2.53Earnings per Share

Shareholders’ Equity

$690MNet Income

$950MDividends Paid

Book Value per Share Excluding Accumulated Other Comprehensive Income

From Year-End 2019, Adjusted for $3.48 Dividends Paid in 2020

6%Increase

In 2020, CNA and the insurance industry rose to meet the many unique challenges presented by the global pandemic. I am immensely proud of how our employees seamlessly transitioned to a remote working environment and how we deployed innovative strategies and tactics to effectively deliver on our commitments to policyholders and to maintain the expert level of support our agents and brokers expect from CNA.

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Strong execution and underlying performance in Property & CasualtyCNA’s resilience and agility in remarkable circumstances allowed us to successfully grow our business as underwriting market conditions strengthened. The global pandemic was a catalyst for claim activity that accelerated already improving Property & Casualty (P&C) insurance pricing, terms and conditions. These hardening market conditions were necessary as the pandemic followed many years of inadequate pricing, elevated frequency and severity of insured catastrophe losses, increasing liability claims costs driven by social inflation, and pressures on investment income due to a protracted low interest rate environment.

In 2020, we achieved 9% Gross Written Premium growth (excluding Captives) and 6% Net Written Premium growth. This robust growth was driven by strong customer retention and new business, both achieving significantly improved pricing and terms and conditions. Notably, we recorded improved underlying margins in each of our three P&C operating segments, and overall we delivered an Underlying Combined Ratio of 93.1% – marking our fourth consecutive year of Underlying Combined Ratio improvement.

Our underlying performance improvement is a function of the core strategic priorities we have institutionalized across CNA over the last four years: continuously enhancing our underwriting-focused culture; attracting, developing and retaining the highest quality talent; advancing our deep specialization through new products and risk solutions; and building long-lasting strategic partnerships with agents and brokers.

The meaningful improvement in our underlying P&C performance offset what otherwise would have been a steeper decline in overall Core Income, which was 25% lower than the prior year, due to losses relating to elevated natural catastrophes, civil unrest and the impacts of COVID-19.

2020 Shareholder Letter

Always building for the futureNotwithstanding unparalleled challenges during the year, CNA’s operating performance was solid. We are tremendously proud of our execution in 2020, and we remain confident in our ability to grow profitably as we continue to evolve and improve our capabilities in order to provide the best insurance solutions for our customers.

Investments in technology and analytics continue to advance our standards of execution. Our improving data management and cloud capabilities have allowed us to launch new tools to enhance the ease of doing business with CNA, while our expanded use of artificial intelligence has enabled predictive insights that augment and supplement the entire underwriting value chain.

As I often observe, our employees are our greatest competitive advantage, and central to our ability to attract and retain top talent is our commitment to Diversity & Inclusion. Our D&I Council and dedicated Employee Resource Groups lead the agenda for engagement across CNA, with education and allyship being critical cornerstones of our ongoing commitment to equality and to building an increasingly inclusive working environment.

2020 marked the sixth consecutive year for which we earned a perfect 100% score on the Human Rights Campaign Foundation’s Corporate Equality Index – the national benchmarking tool on corporate policies and practices pertinent to lesbian, gay, bisexual and transgender employees.

As social unrest unfolded in cities across the United States during the year, racism became a topic of discussion for CNA in a much more transparent way. CNA’s African American Employee Networking Group hosted “A Conversation on Race” where colleagues openly shared experiences. The event significantly increased awareness and empathy across the CNA employee population and sparked ongoing dialogue and action across the company. I cannot emphasize enough that there is no place for intolerance at CNA.

Looking beyond our internal working environment, we continue to support positive improvement within the communities to which our customers belong through volunteerism and corporate philanthropy. Additionally, we utilize our portfolio exposure expertise and Risk Control engineering to help insureds prevent and temper the impacts of climate change, as well as other new and emerging risks.

Excellent financial strengthRobust capital adequacy and strong credit fundamentals reflect the strength and quality of CNA’s balance sheet. We maintain a conservative capital structure, a high-quality investment portfolio, and excellent liquidity – factors four leading rating agencies recognized when they affirmed our financial strength ratings in 2020.

Stable earnings and improved underlying P&C underwriting performance have strengthened our balance sheet and will continue to support our long-term financial strength. Furthermore, we are committed to de-risking our runoff portfolio exposures and in 2020 we took two significant actions to reduce future potential for legacy reserve volatility. We entered into an agreement to cede a portfolio of legacy Excess Workers’ Compensation reserves, and we also meaningfully reduced reserve risk associated with our runoff Long Term Care portfolio by lowering our discount rate assumptions for the second consecutive year. This decision was supported by expectations for a prolonged low interest rate environment going forward.

Thank you for your continued supportOur performance during an extraordinary year is reflective of our strong capabilities. We were well-positioned to capitalize on market opportunities and we demonstrated that CNA can operate effectively in an ever-changing, dynamic environment. The strength of our underlying performance, growth and execution is a testament to our dedicated team.

I would like to thank all our CNA employees for their creativity and passion for the long-term success of CNA, and also to thank our agents and partners for their ongoing collaboration and support. I remain incredibly optimistic about the future for CNA and the opportunities we see ahead.

Dino E. RobustoChairman and Chief Executive OfficerCNA Financial Corporation, February 9, 2021

Dino E. RobustoChairman of the Board andChief Executive OfficerCNA Financial Corporation

Michael A. Bless1

President and Chief Executive OfficerCentury Aluminum Company

Jose O. Montemayor1

PrincipalBlack Diamond Capital Partners I, LP

Don M. Randel1

Retired PresidentThe Andrew W. Mellon Foundation

Dino E. RobustoChairman of the Board andChief Executive OfficerCNA Financial Corporation

Albert J. Miralles Jr.2

Executive Vice President and Chief Financial OfficerCNA Financial Corporation

Elizabeth A. AguinagaExecutive Vice President and Chief Human Resources OfficerCNA Insurance Companies

Michael A. CostonisExecutive Vice President and Chief Operations OfficerCNA Insurance Companies

Headquarters:CNA Financial Corporation151 North Franklin StreetChicago, IL 60606312-822-5000cna.com

Independent Auditors:Deloitte & Touche LLP111 South Wacker DriveChicago, IL 60606

Directors

Executive Officers

André Rice1

Founder and PresidentMuller & Monroe Asset Management, LLC

Kenneth I. SiegelSenior Vice PresidentLoews Corporation

Andrew H. TischCo-Chairman of the BoardLoews Corporation

Benjamin J. TischVice PresidentLoews Corporation

Nick CreaturaPresident and Chief Executive Officer, CanadaCNA Insurance Companies

Daniel P. Franzetti3

Executive Vice President, Worldwide ClaimCNA Insurance Companies

José Ramón González Executive Vice President and General CounselCNA Financial Corporation

Robert J. Hopper4

Executive Vice President and Chief ActuaryCNA Insurance Companies

Transfer Agent:Broadridge Corporate Issuer Solutions, Inc.P.O. Box 1342Brentwood, NY 11717www.shareholder.broadridge.com/cnaPhone U.S. and Canada: 877-456-5752Outside U.S. and Canada: 1-720-414-6894shareholder@broadridge.com

James S. TischPresident and Chief Executive OfficerLoews Corporation

Jane J. WangVice PresidentLoews Corporation

Kevin J. LeidwingerPresident and Chief Operating Officer, CommercialCNA Insurance Companies

Jalil Rehman5

President and Chief Executive Officer,UK and EuropeCNA Insurance Companies

Kevin G. SmithPresident and Chief Operating Officer, SpecialtyCNA Insurance Companies

Douglas M. WormanExecutive Vice President and Chief Underwriting OfficerCNA Insurance Companies

Shareholder Information:The common stock of CNA FinancialCorporation is listed on the New YorkStock Exchange and the Chicago StockExchange. Its trading symbol is CNA.

Investor Relations:Amy C. AdamsSenior Vice President & Treasurerinvestor.relations@cna.com151 North Franklin Street Chicago, IL 60606

1 Member of Audit and Compensation Committees | 2 Assumed role 2/25/20 | 3 Assumed role 4/6/20 | 4 Assumed role 8/24/20 | 5 Assumed role 9/1/20

2020 Form 10-KCNA Financial Corporation

“CNA” is a service mark registered by CNA Financial Corporation with the United States Patent and Trademark Office and the Canadian Intellectual Property Office. Certain CNA Financial Corporation subsidiaries use the “CNA” service mark in connection with insurance underwriting and claims activities. Copyright © 2021 CNA. All rights reserved. 19-0562

151 North Franklin StreetChicago, Illinois 60606

151 North Franklin Street Chicago, Illinois 60606

“CNA” is a registered trademark of CNA Financial Corporation. Certain CNA Financial Corporation subsidiaries use the “CNA” trademark in connection with insurance underwriting and claims activities. Copyright © 2021 CNA. All rights reserved.