Bowhead Specialty Holdings Inc

1. 1

   Merger Proposal

   ManagementBoard: FOR

   Adopt the Agreement and Plan of Merger dated August 2, 2026, and approve the merger and related transactions under which Trident Superior Inc. will merge into Bowhead Specialty Holdings Inc., with each eligible common share converted into the right to receive $34.00 in cash, subject to stated exceptions and appraisal rights.

   More detail

   The proposal asks stockholders to approve the merger agreement and the merger with American Family Mutual Insurance Company, S.I. The transaction would merge Trident Superior Inc. into Bowhead, with Bowhead surviving as a privately held company. Eligible common shares would be converted into the right to receive $34.00 in cash per share, without interest and subject to applicable withholding. Parent would own 100% of the surviving company after closing, and the common shares would cease trading on the NYSE and be deregistered under the Exchange Act. Approval requires both a majority of all outstanding common shares and a majority of the outstanding shares held by Subject Stockholders, excluding Parent, its subsidiaries, and Recused Directors. The Non-Recused Directors negotiated the transaction, obtained a fairness opinion from Ardea, and considered market premiums, the Company’s prospects, industry conditions, alternative transactions, and the limited interest from contacted third parties. They concluded that $34.00 was the highest price Parent was willing to offer and that the agreement’s terms and procedural protections supported approval. Stockholders retain appraisal rights if they satisfy the detailed requirements of Section 262 of the Delaware General Corporation Law. The Board therefore recommends that stockholders vote FOR the Merger Proposal.

2. 2

   Compensation Advisory Proposal

   ManagementBoard: FOR

   Approve, on a non-binding advisory basis, the compensation that will or may become payable to the Company’s named executive officers and that is based on or otherwise relates to the merger.

   More detail

   The proposal asks stockholders to approve, on a non-binding advisory basis, merger-related compensation for the Company’s named executive officers. The disclosed arrangements include cash severance, equity award treatment, benefits, retention awards, post-closing incentive opportunities, and a potential tax gross-up for the chief executive officer. The proxy identifies estimated total merger-related compensation of $32,390,388 for Stephen Sills, $2,784,477 for Brad Mulcahey, and $4,727,297 for David Newman under the stated assumptions. The compensation reflects both single-trigger and double-trigger elements, with many payments dependent on a qualifying termination after the merger. Mr. Sills’ equity awards are generally deferred into a cash-funded arrangement subject to continued employment through the first anniversary, subject to specified accelerated vesting exceptions. Messrs. Mulcahey and Newman may receive retention bonuses, while Mr. Sills and Mr. Newman have post-closing employment arrangements with Parent-related entities. The proposal is required by Section 14A of the Exchange Act and provides stockholders an opportunity to express a view on the compensation disclosures. The vote is not a condition to closing, is not binding on the Company, the Board, or Parent, and the contractual arrangements are not subject to approval. The Board nevertheless recommends that stockholders vote FOR the Compensation Advisory Proposal.

3. 3

   Adjournment Proposal

   ManagementBoard: FOR

   Approve adjournment or postponement of the special meeting if necessary to solicit additional proxies because there are insufficient votes to approve the Merger Proposal.

   More detail

   The proposal asks stockholders to authorize adjournment or postponement of the special meeting if additional time is needed to obtain approval of the Merger Proposal. The principal purpose is to permit the Company and its proxy solicitor to solicit additional proxies when the votes then present are insufficient. The Company states that it does not intend to submit the proposal for a vote if the Merger Proposal has already been approved. An approved adjournment could also provide time to address an insufficient quorum or distribute a legally required supplement or amendment to the proxy statement. Under the Merger Agreement, the Company may adjourn after consultation with Parent for these purposes and in certain circumstances required by law or regulators. Adjournment would allow the Company to seek votes from stockholders who have not voted or who previously voted in a manner that could be changed. The proposal does not itself approve the merger and does not alter the separate voting thresholds for the Merger Proposal. Because all proposals are expected to be non-routine, brokers cannot vote uninstructed shares on this matter. The Board recommends that stockholders vote FOR the Adjournment Proposal.

4. 4

   Other Business

   Management

   Act upon any other business that may properly come before the special meeting or any adjournment or postponement thereof.

   More detail

   The notice includes a standard item allowing stockholders to act on other business that may properly come before the special meeting. No specific additional matter is identified in the proxy statement. The Board states that it was not aware of any such other business as of the proxy statement date. If a stockholder signs and returns a proxy without limiting the proxy authority, the named proxy holders may vote in their discretion on any properly presented matter. This discretionary authority is subject to applicable law and the Board’s stated understanding that the matter must be properly brought before the meeting. The item is distinct from the three substantive proposals concerning the merger, executive compensation, and adjournment. The filing does not identify a shareholder proponent or a separate management resolution beyond the general authorization. No explicit Board recommendation of FOR or AGAINST is provided for this routine catch-all item. Stockholders should therefore understand it as authorization for proxy holders to address unforeseen proper business rather than as a separately analyzed management initiative.

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When is the Bowhead Specialty Holdings Inc 2026 special meeting?

Bowhead Specialty Holdings Inc (BOW) holds its 2026 special shareholder meeting on Friday, November 13, 2026.

What is the record date for the Bowhead Specialty Holdings Inc 2026 meeting?

The record date for the Bowhead Specialty Holdings Inc 2026 meeting is Monday, October 12, 2026. Shareholders of record on or before that date are eligible to vote.

Who are the director nominees for Bowhead Specialty Holdings Inc's 2026 meeting?

The board is presenting 11 director nominees at the Bowhead Specialty Holdings Inc 2026 meeting, listed with their independence status and background.

What proposals will shareholders vote on at the Bowhead Specialty Holdings Inc 2026 meeting?

Shareholders will vote on 4 proposals at the Bowhead Specialty Holdings Inc 2026 meeting, each tagged with who proposed it and the board's recommendation.