American Family to acquire Bowhead Specialty

American Family Mutual Insurance Company, S.I. (“American Family”) today announced that it and Bowhead Specialty Holdings Inc. (NYSE: BOW) (“Bowhead”) have entered into a definitive agreement pursuant to which American Family has agreed to acquire all of the issued and outstanding shares of common stock of Bowhead that it does not currently own for $34.00 per share in cash for a total transaction value of approximately $1.2 billion.

Bowhead is a growing specialty insurance business providing casualty, professional liability and healthcare liability insurance products. Bowhead products are delivered through two complementary underwriting models designed to support sustainable and profitable growth across market cycles: a “craft” model for large, complex, higher-severity risks, and a “digital” model, which includes Baleen Specialty and other small-business offerings (“express”), for smaller, simpler, and scalable business.

​“We’re pleased to welcome Bowhead’s talented team and commercial specialty capabilities to American Family,” said Bill Westrate, chair and chief executive officer of American Family. “Our relationship with Bowhead has continued to grow since our founding investment in 2020. As a minority stockholder and strategic partner, we have seen firsthand the strength of its business model, disciplined execution, and strong market position. We have great confidence in Bowhead’s leadership, employees and culture, and we look forward to supporting the next phase of its growth. Together, we are well positioned to advance our shared long-term objectives while preserving the qualities that have made Bowhead a leader in its market. Bowhead’s capabilities complement our strategy to diversify our commercial portfolio, broaden our product offerings, enhance capital efficiency and drive sustainable profitable growth.”

Bowhead Chief Executive Officer and President, Stephen Sills, commented, “Since Bowhead's founding, it has benefited from a strong and trusting relationship with American Family, whose support and partnership have enabled Bowhead to build the company it is today. Over the years, they have developed a deep understanding of Bowhead’s business, culture, and the underwriting discipline that defines Bowhead. I believe this transaction delivers compelling value to Bowhead’s stockholders while bringing together two organizations that share a long history, aligned values, and a commitment to disciplined underwriting and long-term success. I am proud of what the Bowhead team has accomplished, and I believe this combination recognizes the strength of the Bowhead franchise while continuing to enhance Bowhead’s ability to create value for its insureds, distribution partners and employees. I look forward to joining American Family and continuing to lead the Bowhead franchise.”​

American Family and Bowhead are targeting to close prior to the end of 2026. The transaction is subject to customary closing conditions, including receipt of required regulatory approvals and approvals of Bowhead’s stockholders. American Family will fund the purchase through cash and other liquid investments on hand. The transaction is not subject to any financing conditions or contingency.

Keefe, Bruyette & Woods, A Stifel Company, is serving as the financial advisor to American Family. Willkie Farr & Gallagher LLP is serving as the legal advisor to American Family.​

# # # ​

​About American Family Insurance
American Family Insurance, a mutual holding company based in Madison, Wis., has been serving customers since 1927. We inspire, protect and restore dreams through our insurance products, exceptional service from our agency owners and employees, community investments and creative partnerships. American Family Insurance is the nation’s 12th-largest property/casualty insurance company, ranking No. 226 on the Fortune 500 list. American Family has a current ‘a+’ credit rating through AM Best and has distinction as a “Standing the Test of Time” company, which is represented by having an AM Best financial strength rating of ‘A’ or better for at least 75 years. The company offers American Family-brand products through a network of exclusive agency owners as well as nationwide through key strategic partnerships. American Family Insurance also includes Homesite and Main Street America Insurance. The company has approximately 10,500 employees nationwide.​

Additional Information and Where to Find It
In connection with the transaction, Bowhead will file with the SEC a proxy statement on Schedule 14A, the definitive version of which will be sent or provided to Bowhead’s stockholders. American Family, Bowhead and other affiliates thereof intend to jointly file a transaction statement on Schedule 13E-3 (the “Schedule 13E-3”). Bowhead may also file or furnish other documents with the SEC regarding the transaction. This material is not a substitute for the proxy statement, the Schedule 13E-3 or any other document that Bowhead may file with, or furnish to, the SEC. INVESTORS IN AND STOCKHOLDERS OF BOWHEAD ARE URGED TO READ THE PROXY STATEMENT, THE SCHEDULE 13E-3 AND ANY OTHER RELEVANT DOCUMENTS THAT ARE FILED OR FURNISHED OR WILL BE FILED WITH OR WILL BE FURNISHED TO THE SEC, AS WELL AS ANY AMENDMENTS OR SUPPLEMENTS TO THESE DOCUMENTS, CAREFULLY AND IN THEIR ENTIRETY (IF AND WHEN THEY BECOME AVAILABLE) BECAUSE THEY CONTAIN OR WILL CONTAIN IMPORTANT INFORMATION ABOUT THE TRANSACTION AND RELATED MATTERS. Investors and stockholders may obtain a copy of these documents (when they are filed and become available) free of charge at the SEC’s website at www.sec.gov. Bowhead will also provide a copy of these materials without charge on its website at https://ir.bowheadspecialty.com/.

Participants in the Solicitation
American Family, Bowhead, its executive officers and certain members of its board of directors may be deemed to be participants in the solicitation of proxies from Bowhead’s stockholders in connection with the transaction. Information regarding Bowhead’s directors and executive officers, including a description of their direct interests, by security holdings or otherwise, is contained in Bowhead’s annual proxy statement filed with the SEC on March 16, 2026. A more complete description will be available in the proxy statement on Schedule 14A to be filed regarding the transaction. You may obtain copies of these documents as described in the preceding paragraph filed with, or furnished to, the SEC free of charge. All such documents, when filed or furnished, are available free of charge at the SEC’s website (www.sec.gov) or by directing a request to the investor relations department of Bowhead.