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CNA Financial Corporation provides commercial property and casualty insurance products in the United States and internationally. It operates through Specialty, Commercial, International, Life & Group, and Corporate & Other segments. The company offers professional liability coverages and risk management services to various professional firms, including architects, real estate agents, and accounting and law firms; directors and officers, employment practices, fiduciary, and fidelity and cyber coverages to small and mid-size firms, public and privately held firms, and not-for-profit organizations; professional and general liability, as well as associated casualty coverages for healthcare industry; surety and fidelity bonds; and warranty and alternative risks products. It also provides property, marine, boiler, and machinery coverage insurance products; casualty insurance products comprising workers' compensation, general and product liability, commercial auto, umbrella, and excess and surplus coverages; specialized loss-sensitive insurance programs and total risk management services; and run-off long term care policies. The company was founded in 1853 and is based in Chicago, Illinois. CNA Financial Corporation operates as a subsidiary of Loews Corporation.

Fairfax Financial Holdings Limited, through its subsidiaries, provides property and casualty insurance and reinsurance, and investment management services in the United States, Canada, Asia, and internationally. The company operates through Property and Casualty Insurance and Reinsurance, Life insurance and Run-off, and Non-Insurance Companies segments. It insures against losses to property from fire, explosion, earthquake, windstorm, flood, terrorism, boiler explosion, machinery breakdown, and construction defects, as well as underwrites automobile, commercial and personal property, and crop insurance. The company also offers workers' compensation, automobile, employer's liability, accident and health, medical malpractice, professional liability, and umbrella coverage insurance products; marine, aerospace, surety risk, and other risks and liabilities insurance products; and reinsurance products. In addition, it franchises, owns, and operates restaurants; retails sports lifestyle products; provides integrated travel and travel-related financial services, as well as advanced digital tools for agriculture; owns and operates holiday resorts; originates, processes, and distributes value-added pulses and staple foods; develops, manages, and invests in hospitality real estate. The company was formerly known as Markel Financial Holdings Limited and changed its name to Fairfax Financial Holdings Limited in 1987. Fairfax Financial Holdings Limited was incorporated in 1951 and is headquartered in Toronto, Canada.

Lemonade, Inc. provides various insurance products through various channels in the United States, Europe, and the United Kingdom. Its insurance products include stolen or damaged property, and personal liability that protects its customers if they are responsible for an accident or damage to another person or their property. The company also offers renters, homeowners, car, pet, and life insurance products, as well as landlord insurance policies. In addition, it operates as an agent for other insurance companies. The company was formerly known as Lemonade Group, Inc. and changed its name to Lemonade, Inc. Lemonade, Inc. was incorporated in 2015 and is headquartered in New York, New York.

Everest Re Group, Ltd., through its subsidiaries, provides reinsurance and insurance products in the United States, Bermuda, and internationally. The company operates through Reinsurance Operations and Insurance Operations segments. The Reinsurance Operations segment writes property and casualty reinsurance; and specialty lines of business through reinsurance brokers, as well as directly with ceding companies in the United States, Bermuda, Ireland, Canada, Singapore, Switzerland, and the United Kingdom. The Insurance Operations segment writes property and casualty insurance directly, as well as through brokers, surplus lines brokers, and general agents in the United States, Bermuda, Canada, Europe, South America, France, Germany, Spain, Canada, Chile, the United Kingdom, Ireland, and the Netherlands. The company also provides treaty and facultative reinsurance products; admitted and non-admitted insurance products; and property and casualty reinsurance and insurance coverages, including marine, aviation, surety, errors and omissions liability, directors' and officers' liability, medical malpractice, mortgage reinsurance, other specialty lines, accident and health, and workers' compensation products. In addition, it offers commercial property and casualty insurance products through wholesale and retail brokers, surplus lines brokers, and program administrators. The company was founded in 1973 and is headquartered in Hamilton, Bermuda.

W. R. Berkley Corporation, an insurance holding company, operates as a commercial lines writers worldwide. It operates in two segments, Insurance and Reinsurance & Monoline Excess. The Insurance segment underwrites commercial insurance business, including excess and surplus lines, admitted lines, and specialty personal lines. This segment also provides accident and health insurance and reinsurance products; insurance for commercial risks; casualty and specialty environmental products; specialized insurance coverages for fine arts and jewelry exposures; excess liability and inland marine coverage for small to medium-sized insureds; and commercial general liability, umbrella, professional liability, directors and officers, commercial property, and surety products, as well as products for technology, and life sciences and travel industries. In addition, this segment offers cyber risk solutions; crime and fidelity insurance products; medical professional coverages; workers' compensation insurance products; general insurance; personal lines insurance solutions, including home, condo/co-op, auto, and collectibles; automobile, law enforcement, public officials and educator's legal, and employment practices liability, as well as incidental medical and property and crime insurance products; at-risk and alternative risk insurance program management services; professional liability; energy and marine risks; and provides insurance products to the Lloyd's marketplace. The Reinsurance & Monoline Excess segment provides treaty and facultative reinsurance solutions; property and casualty reinsurance; facultative reinsurance products include automatic, semi-automatic and individual risk assumed reinsurance; and turnkey products such as cyber, employment practices liability insurance, liquor liability insurance and violent events. The company was founded in 1967 and is headquartered in Greenwich, Connecticut.