EXHIBIT (C)(12)
Published on August 31, 2026
Exhibit (c)(12)
Fairness Opinion Presentation Prepared for the Board of Directors of: Regarding
Project Trident July 30, 2026 CONFIDENTIAL
Disclaimer Page 2 PRIVATE AND CONFIDENTIAL This presentation (this
"Presentation") has been prepared by Keefe, Bruyette & Woods, Inc. ("KBW") for the exclusive use of the Board of Directors (the "Board") of American Family Mutual Insurance Company, S.I. (“AmFam” or "Buyer") in connection with KBW's
presentation to the Board at a meeting to be held on July 30, 2026. This Presentation has been prepared further to KBW's rendering of an opinion (the "Opinion") to the Board as to the fairness, from a financial point of view, to AmFam of the
Merger Consideration to be paid by AmFam in the proposed merger (the "Merger" or the "Transaction") of a wholly-owned subsidiary of AmFam with and into Bowhead Specialty Holdings Inc. (NYSE: BOW) ("Bowhead"). This Presentation is qualified in its
entirety by the written Opinion delivered to the Board, including the assumptions and qualifications therein. This Presentation contains information obtained from publicly available sources and from materials provided to KBW by AmFam and
Bowhead. In conducting our analyses, we have, with the consent of AmFam, assumed and relied upon, without independent verification, the accuracy and completeness of all of the financial and other information reviewed by us, and we have not
assumed any responsibility or liability for independent verification of, or the accuracy or completeness of, such information. KBW did not conduct any independent verification or any appraisal or physical inspection of properties, assets or
liabilities or evaluate the solvency, financial capability or fair value of Bowhead or AmFam under any state or federal laws, including those relating to bankruptcy, insolvency or other matters, and is not expressing a view or opining as to any
terms of the Merger (except to the extent expressly set forth in the written Opinion) or the terms of any other transaction undertaken by AmFam. We have assumed that the financial and operating forecasts and projections of Bowhead (which were
adjusted, including, among other things, to give effect to the cost savings and operating synergies expected to result or be derived from the Merger) that were provided to us by AmFam management and we were directed by AmFam to use have been
reasonably prepared and represent the best currently available estimates and judgments of AmFam management as to the future financial and operating performance of Bowhead. We have assumed that the foregoing information provides a reasonable basis
upon which we can form the Opinion. We express no view as to any such forecasts, projections or as to the other matters covered thereby, or estimates or the assumptions or bases therefor. The Opinion (and this Presentation) is based upon
economic, market and other conditions as they exist and can be evaluated as of its date (or such other dates as reflected therein). KBW believes that its analysis must be considered as a whole and that selecting portions of such analysis and the
factors considered by it could create an incomplete view of the process underlying its conclusions. Any analysis of this type is subject to uncertainties and contingencies, all of which are difficult to predict and are beyond the control of the
firm preparing the analysis. There is currently significant volatility in the stock and other financial markets arising from global tensions and political division, economic uncertainty, recently announced actual or threatened imposition of
tariff increases, inflation, and prolonged higher interest rates. It is understood that subsequent developments may affect the conclusions reached in the Opinion and that KBW does not have an obligation to update, revise or reaffirm the Opinion
or this Presentation. This Presentation and the information contained herein have been prepared solely for the Board and may not be used by any other person without the express prior written consent of KBW. Any party receiving these materials
(other than the Board) is not authorized to rely on these materials for any purpose. AmFam acknowledges that it shall not disclose to any person the existence of this Presentation or the Opinion, any view expressed by KBW in connection herewith
(in writing or otherwise) or any portion hereof or thereof, or KBW's engagement, without KBW's express written consent. This Presentation and the Opinion, and the materials and financial models used by KBW in preparing this Presentation and the
Opinion, have been developed by and are proprietary to KBW and are protected under applicable copyright laws. Not in limitation of any of the foregoing, any recipient thereof, by virtue of such receipt, agrees that it will not reproduce,
distribute or make publicly available all or any portion of the Opinion, this Presentation or such models or other materials contained therein without the prior written consent of KBW.
Important Notice Page 2 PRIVATE AND CONFIDENTIAL KBW has acted exclusively for
the Board in rendering the Opinion and will receive a fee from AmFam for its services The Opinion speaks only as of its date and is necessarily based on economic, market, financial and other conditions as they exist on, and information made
available to us as of, such date. Subsequent developments may affect the conclusion reached in the Opinion and KBW does not have any obligation to update, revise or reaffirm the Opinion A portion of KBW's fee is payable upon the rendering of the
Opinion, and a significant portion of KBW's fee is contingent upon the successful completion of the Transaction In conducting its review and arriving at the Opinion, KBW has relied upon and assumed the accuracy and completeness of all financial
and other information provided to or discussed with us or publicly available and KBW has not independently verified the accuracy or completeness of any such information or assumed any responsibility or liability for such verification, accuracy,
or completeness The issuance of the Opinion has been approved by our Fairness Opinion Committee Other than in connection with this present engagement, KBW has not provided investment banking or financial advisory services to AmFam during the
past two years KBW has provided investment banking and financial advisory services to Bowhead during the past two years KBW may provide investment banking and financial advisory services to AmFam or Bowhead in the future, for which KBW may
receive compensation A sales and trading relationship exists between a KBW broker-dealer affiliate and AmFam
Bowhead Overview 02 01 Transaction Overview Table of Contents Financial
Analysis 03 Appendix 04 Page 2 PRIVATE AND CONFIDENTIAL
Transaction Overview Page 2 PRIVATE AND CONFIDENTIAL
Key Transaction Terms Page 2 PRIVATE AND CONFIDENTIAL Buyer American Family
Mutual Insurance Company, S.I. Target Bowhead Specialty Holdings Inc. (NYSE: BOW) Form of Consideration 100% cash Merger Consideration $34.00 per share Implied Equity Value $1,180 million1 Treatment of Common Equity Awards & AmFam
Warrant RSUs: Each non-CEO Company RSU converts at the Effective Time into a beneficial interest in an AmFam- funded escrow account with cash equal to the number of RSUs multiplied by the Merger Consideration, retaining the original vesting,
forfeiture and settlement terms and paid out in cash plus AFR (“Applicable Federal Rate”) interest upon settlement CEO RSUs: CEO RSUs paid out according to Sills Employment Agreement CEO PSUs: CEO PSUs are cashed out into a separate escrow,
with payment plus AFR interest deferred until the first anniversary of closing subject to continued employment — accelerated on a termination without Cause, resignation for Good Reason, or death/disability, and forfeited on any other departure
before then Warrant: AmFam Warrant2 will terminate and the underlying shares will be canceled with no payment or distribution at closing Required Approvals Approval by Bowhead stockholders Required Regulatory Approvals and HSR Act waiting
periods expired or terminated Expected Closing Q4 2026 Company Termination Fee 3.00% DISCLAIMER: Reflects draft Merger Agreement dated July 29, 2026 (the "Draft Merger Agreement") and input from AmFam. This overview is not intended to be a
comprehensive listing of all relevant terms contained in the Draft Merger Agreement or any other agreement or a complete description of the terms described in this overview, for which reference should only be made to the Draft Merger Agreement
and any other definitive agreements. Capitalized terms not defined herein have the definitions given them in the Draft Merger Agreement. Based on the Merger Consideration and 32,943,005 shares of Bowhead common shares outstanding and dilution
from 1,415,210 RSUs and 339,997 PSUs; the AmFam Warrant, which will be canceled in connection with the Transaction, has been excluded as directed by AmFam. AmFam Warrant is the warrant issued to AmFam in connection with Bowhead's May 2024 IPO to
purchase 1,670,721 shares of common stock at a $17.00 exercise price, vesting 20% per year over five years and exercisable until the tenth anniversary of issuance.
Merger Consideration (Per Share as Defined in Draft Merger
Agreement) $34.00 Aggregate Transaction Value ($ in millions) Aggregate Transaction Value of Common Shares 1 $1,120 Aggregate Transaction Value of RSUs and PSUs 2 $60 Aggregate Transaction Value $1,180 Premium to Metric Current Stock
Price (29-Jul-2026) $31.96 6.4% 30-Day Volume Weighted Average Price (VWAP) (29-Jul-2026) $30.19 12.6% Price to Diluted EPS 3, 4 Preliminary Q2 2026 LTM Adjusted EPS $1.89 17.9x 2026 Projected EPS, as Adjusted by
AmFam $2.27 15.0x 2027 Projected EPS, as Adjusted by AmFam $2.55 13.4x 2028 Projected EPS, as Adjusted by AmFam $2.74 12.4x 2027 Median Consensus Estimated EPS 5 $2.38 14.3x 2028 Median Consensus Estimated EPS 5 $2.79 12.2x Price /
Book Value 3 Preliminary Q2 2026 Bowhead Book Value Per Share (BVPS) $14.39 2.36x Page 2 PRIVATE AND CONFIDENTIAL Implied Transaction Multiples Note: LTM = Last Twelve Months. Multiples may not tie exactly due to rounding. Based on the
Merger Consideration ($34.00) and 32,943,005 shares of Bowhead common shares outstanding and excludes the AmFam Warrant, which is cancelled in connection with the Transaction, as directed by AmFam. Based on the Merger Consideration ($34.00) and
dilution from 1,415,210 RSUs and 339,997 PSUs. Q2 2026 Bowhead metrics reflect Bowhead preliminary unaudited results for the six-month period ending June 30, 2026. Diluted adjusted earnings per share is defined as adjusted net income divided by
the weighted average common shares outstanding for the period, reflecting the dilution that may occur if equity- based awards are converted into common stock equivalents as calculated using the treasury stock method. Adjusted net income is
defined as net income excluding the impact of net realized investment (losses) gains, non-operating expenses, foreign exchange losses (gains), and certain strategic initiatives. Adjusted net income excludes the impact of certain items that may
not be indicative of underlying business trends, operating results, or future outlook, net of tax impact. Bowhead calculates the tax impact only on adjustments that would be included in calculating Bowhead’s income tax expense using the estimated
tax rate at which Bowhead received a deduction for these adjustments. See page 26 for a detailed reconciliation of non-GAAP measures. 2027 and 2028 consensus estimates reflect median consensus estimates per FactSet as of July 29, 2026.
Bowhead Overview Page 2 PRIVATE AND CONFIDENTIAL
Source: BOW filings, earnings calls and Bowhead preliminary unaudited results
pending auditor review ahead of Q2 earnings release. 2025 Bowhead Insurance Company statutory annual statement, measured based on direct written premium. Adjusted net income is defined as net income excluding the impact of net realized
investment losses, non-operating expenses, loss on extinguishment of credit facility, foreign exchange losses (gains), and certain strategic initiatives. Adjusted net income excludes the impact of certain items that may not be indicative of
underlying business trends, operating results, or future outlook, net of tax impact. Bowhead calculates the tax impact only on adjustments that would be included in calculating Bowhead’s income tax expense using the estimated tax rate at which
Bowhead received a deduction for these adjustments. See page 26 for a detailed reconciliation of non-GAAP measures. Page 9 PRIVATE AND CONFIDENTIAL Adjusted return on equity is adjusted net income as a percentage of average mezzanine and
stockholders’ equity. See page 26 for reconciliation of non-GAAP measures. 2025 reflects annual GAAP results as of December 31, 2025. Q2 2026 results reflect unaudited results pending auditor review ahead of Q2 earnings release. Bowhead –
Company Snapshot Bowhead Specialty Holdings Inc. (NYSE: BOW) (“Bowhead”) is a New York-headquartered commercial, specialty P&C insurer focused on the U.S. excess & surplus lines (“E&S”) market Founded in late 2020 by industry
veteran CEO Stephen Sills with backing from Gallatin Point Capital LLC (“Gallatin Point”) and AmFam Stephen Sills has 40+ years of specialty P&C industry experience, including previously founding two specialty insurers (Executive Risk, Inc.
and Darwin Professional Underwriters, Inc.) that each went public and subsequently sold to a strategic buyer Since inception, Bowhead has operated in a strategic partnership with AmFam Bowhead originates and underwrites all Bowhead
policies AmFam provides A.M. Best Company, Inc. “A” financial strength rated paper and nationwide admitted and E&S licensing for Bowhead; AmFam receives a ceding fee Bowhead assumes 100% of the risk of Bowhead policies from AmFam; Bowhead
then purchases both quota share and excess of loss reinsurance from third-party reinsurers (including AmFam) and retains significant risk exposure Bowhead writes casualty, professional liability and healthcare liability with ~80% of premiums
written on a non-admitted basis1 Business is written across four underwriting divisions: Casualty (~64% of gross written premiums), Professional Liability (~20%), Healthcare Liability (~13%) and Baleen Specialty (~3%) Products are underwritten
through two complementary models: a “craft” model (custom underwriting of large/complex risks on an individual basis) and a “digital” model (streamlined, tech-enabled underwriting of small risks) Business is distributed through wholesale and
retail brokers For the year ended December 31, 2025, Bowhead reported gross written premium growth of 24% to $863 million, net written premiums of $558 million, combined ratio of 96.5%, adjusted net income of $56 million2 and adjusted return on
equity of 13.6%3; equity of $449 million4 For the first six months ended June 30, 2026, Bowhead reported gross written premium of $515 million, net written premiums of $321 million, combined ratio of 95.6%, adjusted net income of $32 million2
and annualized adjusted return on equity of 13.9%3; equity of $474 million4 Balance sheet has no reserves from pre-2020 accident years As of December 31, 2025, Bowhead had a $1.4 billion, 100% fixed-income investment portfolio (average “AA”
quality, 4.6% book yield)4 At year-end 2025, debt/total capitalization ratio was ~25% with no preferred stock and an undrawn $35 million revolver4 In November 2025, Bowhead issued $150 million of 7.75% senior notes due in 2030; Morningstar DBRS
assigned Bowhead Specialty Holdings Inc. an issuer credit rating of BBB (high) in connection with this issuance Bowhead completed its initial public offering in May 2024 for a total offering size of $147.2 million; the deal was 100% primary with
proceeds primarily used to contribute statutory capital to its insurance subsidiary to support continued growth As of May 31, 2026, AmFam owns 4.7 million common shares (~14%) of Bowhead and Gallatin Point owns 9.0 million common shares (~27%).
In addition, AmFam owns the AmFam Warrant (right to purchase 1.67 million shares at $17.00 per share, subject to certain terms and conditions). Per the Draft Merger Agreement, the AmFam Warrant will terminate at the Effective Time.
Bowhead – Summary Historical GAAP Financial Results Page 13 PRIVATE AND
CONFIDENTIAL In millions, except per share data Years Ended December 31, Six Months Ended June 30, 2022A 2023A 2024A 2025A 2025A 2026A Preliminary Gross Written Premium $356.9 $507.7 $695.7 $862.8 $407.2 $514.6 Net Written
Premium $245.1 $334.7 $451.4 $558.2 $265.6 $321.4 Net Premium Earned $182.9 $263.9 $385.1 $491.7 $229.0 $280.8 Net Investment Income $4.7 $19.4 $40.1 $57.8 $26.2 $36.8 Net Realized Gains
(Losses) - - ($0.0) $0.0 $0.0 ($0.0) Other Insurance Income $0.0 $0.1 $0.4 $2.0 $0.8 $2.0 Total Revenue $187.6 $283.4 $425.7 $551.6 $256.0 $319.5 Net Loss and Loss Adj.
Expenses $111.8 $166.3 $248.1 $328.0 $152.3 $188.4 Net Acquisition Expenses $15.2 $20.9 $32.4 $46.5 $20.8 $29.7 Operating Expenses $46.0 $63.5 $89.1 $102.3 $49.8 $52.2 Underwriting
Expenses $172.9 $250.7 $369.6 $476.8 $222.9 $270.3 Warrant Expense - - $1.9 $3.1 $1.6 $1.6 Interest and Financing Fees - - $0.7 $2.0 $0.5 $6.4 Other Non-Operating Expenses - $0.6 $2.9 $2.3 $0.6 $0.0 Total
Expenses $172.9 $251.3 $375.1 $484.3 $225.6 $278.3 Net Income $11.3 $25.0 $38.2 $53.8 $23.8 $32.1 Adjusted Net Income (Non-GAAP)1 $11.3 $26.2 $42.7 $55.6 $24.2 $32.2 Diluted Adjusted EPS
(Non-GAAP)1 $0.47 $1.09 $1.44 $1.65 $0.72 $0.96 Key Underwriting Ratios Loss Ratio 61.1% 63.0% 64.4% 66.7% 66.5% 67.1% Expense Ratio 33.5% 31.9% 31.4% 29.8% 30.4% 28.5% Combined
Ratio 94.6% 94.9% 95.8% 96.5% 96.9% 95.6% Balance Sheet Cash & Investments $363.6 $683.2 $1,112.0 $1,604.8 $1,113.3 $1,750.0 Debt - - - $146.4 - $146.6 Total Equity $83.4 $192.1 $370.4 $449.3 $407.8 $473.9 Book
Value Per Share $3.47 $8.00 $11.34 $13.70 $12.44 $14.39 Source: BOW filings and Bowhead preliminary unaudited results pending auditor review ahead of Q2 earnings release. (1) Diluted adjusted earnings per share is defined as adjusted net
income divided by the weighted average common shares outstanding for the period, reflecting the dilution that may occur if equity-based awards are converted into common stock equivalents as calculated using the treasury stock method. Adjusted net
income is defined as net income excluding the impact of net realized investment (losses) gains, non-operating expenses, foreign exchange losses (gains), and certain strategic initiatives. Adjusted net income excludes the impact of certain items
that may not be indicative of underlying business trends, operating results, or future outlook, net of tax impact. Bowhead calculates the tax impact only on adjustments that would be included in calculating Bowhead’s income tax expense using the
estimated tax rate at which Bowhead received a deduction for these adjustments. See page 26 for a detailed reconciliation of non-GAAP measures.
Financial Analysis Page 13 PRIVATE AND CONFIDENTIAL
Overview of Valuation Methodologies (1) Selected Companies include AFG, ASIC, KNSL,
MKL, PLMR, SKWD, RLI, WRB. Selected Companies Analysis Review of trading multiples, including price to book value and price to 2027E EPS, for selected publicly-listed specialty P&C insurance companies1 Applied the 25th and 75th percentile
of each multiple to the applicable Bowhead metric, as adjusted by AmFam, to imply a range of equity values Also considered a regression of price to book value to return on equity analysis Selected Transactions Analysis Review of publicly
available information relating to acquisitions of specialty P&C carriers since 2016, including price to earnings and price to book value multiples for each selected transaction Applied the 25th and 75th percentile range of the selected
precedent transaction multiples to applicable Bowhead metric, as adjusted by AmFam, to arrive at a range of implied equity values Dividend Discount Model Analysis Discount future dividends and calculate terminal equity value to projected
closing date of 12/31/26 Future dividends and GAAP equity per Bowhead projections, as adjusted by AmFam Terminal equity value calculated across a range of price / book value multiples of 1.75x – 2.75x Applied range of selected discount rates
for Bowhead using capital asset pricing model Page 13 PRIVATE AND CONFIDENTIAL
$31.28 $30.13 $31.65 $18.75 $20.67 $26.54 $51.31 $43.55 $38.69 $32.48 $33.16 $41.29 Financial
Analysis Overview Source: FactSet, SNL Financial, company filings and Bowhead preliminary unaudited results pending auditor review ahead of Q2 earnings release. Note: Implied Merger Consideration Ranges may not tie exactly due to rounding.
Market data as of July 29, 2026. Selected Companies includes AFG, ASIC, KNSL, MKL, PLMR, SKWD, RLI, WRB. Preliminary Q2 2026 metrics reflect Bowhead preliminary unaudited results for the six-month period ending June 30, 2026. Selected
Transactions includes acquisitions of specialty P&C insurers announced since the beginning of 2016 with deal values over $250M and less than $5B and one or more publicly available data points to calculate GAAP metrics. Diluted adjusted
earnings per share is defined as adjusted net income divided by the weighted average common shares outstanding for the period, reflecting the dilution that may occur if equity-based awards are converted into common stock equivalents as calculated
using the treasury stock method. Adjusted net income is defined as net income excluding the impact of net realized investment (losses) gains, non-operating expenses, foreign exchange losses (gains), and certain strategic initiatives. Adjusted net
income excludes the impact of certain items that may not be indicative of underlying business trends, operating results or future outlook, net of tax impact. Bowhead calculates the tax impact only on adjustments that would be included in
calculating Bowhead’s income tax expense using the estimated tax rate at which Bowhead received a deduction for these adjustments. Selected Companies Analysis1 2.17x – 3.57x Price to Book Value Preliminary Q2 2026 BVPS: $14.39 2 Selected
Companies Analysis 1 11.8x - 17.1x Price to FY1 EPS 2027E Projected EPS, as Adjusted by AmFam: $2.55 Selected Companies Analysis 1 2027E ROAE Regression: 2.20x – 2.69x Price to Book Value Preliminary Q2 2026 BVPS: $14.39 2 Selected
Transactions Analysis 3 1.30x – 2.26x Price to Book Value Preliminary Q2 2026 BVPS: $14.39 2 Selected Transactions Analysis 3 10.9x – 17.5x Price to LTM EPS Preliminary Q2 2026 LTM Adjusted EPS: $1.89 2,4 Dividend Discount Model Analysis Exit
Multiple: 1.75x-2.75x Discount Rate: 7.5%-11.5% Implied Merger Consideration Range $24.00 $34.00 $44.00 Page 13 PRIVATE AND CONFIDENTIAL Merger Consideration: $34.00 per share $14.00 $54.00
Selected Companies Analysis Page 13 PRIVATE AND CONFIDENTIAL
In millions, except per share data Price Market Return on Avg Equity Price
/ Price / EPS Company Ticker 07/29/26 Cap. 2026E 2027E MRQ Book 2026E 2027E Bowhead Specialty Holdings Inc. (Current Trading) BOW $31.96 $1,050 13.6% 14.5% 2.29x 16.2x 13.5x Bowhead (Proposed
Transaction) BOW $34.00 1 $1,180 2 13.6% 14.5% 2.36x3 17.2x 14.3x W. R. Berkley Corporation WRB $75.65 $29,385 18.1% 16.4% 2.85x 15.6x 15.5x Markel Group Inc. MKL $2,015.00 $25,215 7.3% 7.3% 1.39x 18.1x 17.0x American
Financial Group, Inc. AFG $143.51 $11,924 19.4% 18.7% 2.55x 12.3x 12.0x Kinsale Capital Group, Inc. KNSL $376.67 $8,580 23.5% 21.3% 4.22x 17.7x 17.4x RLI Corp. RLI $65.65 $6,025 15.0% 14.6% 3.44x 22.6x 24.2x Palomar
Holdings, Inc. PLMR $142.91 $3,788 25.1% 23.4% 3.95x 14.4x 13.0x Skyward Specialty Insurance Group, Inc. SKWD $62.52 $2,535 18.0% 17.2% 2.27x 12.9x 11.5x Ategrity Specialty Insurance Company
Holdings ASIC $24.64 $1,184 15.0% 15.8% 1.88x 12.2x 10.0x Average Median 75th Percentile 25th
Percentile 17.7% 18.1% 20.5% 15.0% 16.8% 16.8% 19.3% 15.5% 2.82x 2.70x 3.57x 2.17x 15.7x 15.0x 17.8x 12.7x 15.1x 14.2x 17.1x 11.8x Selected Companies Analysis Page 13 PRIVATE AND CONFIDENTIAL Source(s): FactSet, SNL
Financial, company filings. Average, Median, 25th and 75th percentiles exclude Bowhead. Note: MRQ = Most Recent Quarter. Results at or for the period ended March 31, 2026 except for WRB, KNSL, and RLI, which reflect results at or for the period
ended June 30, 2026. Note: Return on Average Equity and EPS (used to calculate Price / EPS) reflect median consensus estimates per FactSet as of July 29, 2026. Bowhead Merger Consideration. Based on the Merger Consideration and 32,943,005
shares of Bowhead common shares outstanding and dilution from 1,415,210 RSUs and 339,997 PSUs; excludes the AmFam Warrant, which is cancelled in connection with the Transaction, as directed by AmFam. Reflects Bowhead preliminary unaudited
results for the six-month period ending June 30, 2026. Book value per share is presented on a fully diluted basis; all other companies shown reflect book value per common share.
Selected Companies Analysis - Regression 2027E Return on Average
Equity MKL WRB KNSL RLI PLMR AFG SKWD ASIC y = 16.016x + 0.1234 R2 = 0.6057 0.00x 1.00x 2.00x 3.00x 4.00x 5.00x 0.0% 5.0% 10.0% 15.0% 2027E Return on Avg. Equity 20.0% 25.0% Price / MRQ Book Value Implied Valuation 2027E
Price / ROAE MRQ BVPS 7.0% 1.24x 9.0% 1.56x 11.0% 1.89x 13.0% 2.21x 14.5% 2.44x 15.0% 2.53x 17.0% 2.85x -10% 2.20x +10% 2.69x Source(s): FactSet, SNL Financial, company filings and Bowhead preliminary unaudited results pending
auditor review ahead of Q2 earnings release. Results at or for the period ended March 31, 2026 except WRB, KNSL, and RLI, which are at or for the period ended June 30, 2026. Consensus estimates reflect median consensus estimates per FactSet as
of July 29, 2026. (1) Q2 2026 Bowhead metrics reflect Bowhead preliminary unaudited results for the six-month period ending June 30, 2026. Implied Per Share Value of Bowhead = $35.171 Page 13 PRIVATE AND CONFIDENTIAL
Selected Transactions Analysis Page 13 PRIVATE AND CONFIDENTIAL
Note: Deal value and multiples at time of announcement. Multiples based on GAAP
financials. Average, Median, 25th and 75th Percentile exclude Transaction. Source(s): FactSet, SNL Financial, company filings and Bowhead preliminary unaudited results pending auditor review ahead of Q2 earnings release. Based on KBW judgement
based in line of business focus. Based on the Merger Consideration and 32,943,005 shares of Bowhead common shares outstanding and dilution from 1,415,210 RSUs and 339,997 PSUs; excludes the AmFam Warrant, which is cancelled in connection with
the Transaction, as directed by AmFam. Reflects Bowhead preliminary unaudited results for the six-month period ending June 30, 2026. Calculated using diluted adjusted earnings per share. Diluted adjusted earnings per share is defined as
adjusted net income divided by the weighted average common shares outstanding for the period, reflecting the dilution that may occur if equity-based awards are converted into common stock equivalents as calculated using the treasury stock method.
Adjusted net income is defined as net income excluding the impact of net realized investment (losses) gains, non-operating expenses, foreign exchange losses (gains), and certain strategic initiatives. Adjusted net income excludes the impact of
certain items that may not be indicative of underlying business trends, operating results, or future outlook, net of tax impact. Bowhead calculates the tax impact only on adjustments that would be included in calculating Bowhead’s income tax
expense using the estimated tax rate at which Bowhead received a deduction for these adjustments. See page 26 for a detailed reconciliation of non-GAAP measures. Calculated using 2024 GAAP net income. Calculated using UK GAAP net assets as of
12/31/2025. Calculated using UK GAAP profit for fiscal year 2025. Calculated using the commitment of $2.1 billion in unlevered shareholders' equity delivered at closing. Calculated using net income (loss) from continuing operations. Page 18
PRIVATE AND CONFIDENTIAL Calculated using fair value of net tangible assets acquired. Aggregate fully diluted equity value, calculated as the product of the $54.00 per share merger consideration and ~91.2M fully diluted
shares. Date Acquirer Target Deal Value ($M) Price / GAAP Book Value LTM GAAP Net Income TBD American Family Mutual Insurance Company, S.I. Bowhead Specialty Holdings Inc. $1,180 2 2.36x 3 3,4 17.9x 12/18/25 Howard Hughes
Holdings, Inc. Vantage Group Holdings $2,100 1.50x 10.7x 10/30/25 Palomar Holdings, Inc. The Gray Casualty & Surety Company $300 2.31x NA 09/25/25 DB Insurance Co, Ltd. The Fortegra Group, Inc. $1,650 2.26x 11.8x
5 09/18/25 Radian Group, Inc. Inigo Limited $1,671 1.43x 6 7.8x 7 09/02/25 Skyward Specialty Insurance Group Apollo Group Holdings Limited $555 2.56x 6 11.2x 7 08/27/25 Sompo Holdings, Inc. Aspen Insurance Holdings
Limited $3,473 1.30x 10.4x 03/19/25 The Doctors Company ProAssurance Corporation $1,315 1.06x 24.2x 05/22/23 RenaissanceRe Holdings Ltd. Validus Re $2,985 1.42x 8 NM 02/08/23 Brookfield Reinsurance Argo Group International
Holdings, Ltd. $1,065 0.90x NM 02/16/21 Progressive Corporation Protective Insurance Corporation $338 0.96x NM 01/15/21 Towerbrook and Further Global ProSight Global, Inc. $586 0.92x 14.0x 9 08/22/18 The Hartford Financial
Services Group, Inc. Navigators Group Inc. $2,150 1.69x 34.2x 07/26/17 Markel Corporation State National Companies, Inc. $919 2.76x 16.4x 05/02/17 Intact Financial Corporation OneBeacon Insurance Group,
Ltd. $1,732 1.66x 18.5x 02/01/17 Markel Corporation SureTec Financial Corporation $250 3.26x10 NA 12/18/16 Fairfax Financial Holdings Limited Allied World Assurance Company Holdings, AG $4,925 11 1.35x 16.5x 12/05/16 Liberty
Mutual Ironshore Inc. $2,935 1.38x NM Average Median 1.69x 1.43x 16.0x 14.0x 75th Percentile 2.26x 17.5x 25th Percentile 1.30x 10.9x Selected Transactions Analysis Includes acquisitions of specialty P&C insurers1 announced
since the beginning of 2016 with deal values over $250M and less than $5B and one or more publicly available data points to calculate GAAP metrics
Dividend Discount Model Analysis Page 19 PRIVATE AND CONFIDENTIAL
Dividend Discount Model Analysis Page 19 PRIVATE AND CONFIDENTIAL All assumptions
as directed to use by AmFam Minimum operating leverage, defined as net premium written to statutory surplus, of 1.50x AmFam adjusted Bowhead’s projected growth, combined ratio, investment yield, required capitalization and other AmFam-specific
assumptions to reflect AmFam’s post-Transaction view of the business Bowhead Earnings: Bowhead projections as adjusted by AmFam1 – 2027: – 2028: – 2029: – 2030: – 2031: $88 million $95 million $121 million $141 million $160
million GAAP Equity: Bowhead projections as adjusted by AmFam, prior to purchase accounting as directed by AmFam – 2027: – 2028: – 2029: – 2030: – 2031: $353 million $403 million $448 million $490 million $526 million Assumes a tax
rate of 21% Applied terminal multiple to 2031 projected GAAP Equity sensitized across a range of 1.75x - 2.75x price to book value Calculated present value of dividends and terminal value across a discount rate range of 7.5% - 11.5% (1) See
page 27 for additional detail.
Terminal Book Value
Multiple 1.75x 2.00x 2.25x 2.50x 2.75x $30.73 $33.37 $36.01 $38.65 $41.29 $29.60 $32.12 $34.65 $37.16 $39.68 $28.53 $30.93 $33.35 $35.75 $38.16 $27.51 $29.81 $32.12 $34.41 $36.71 $26.54 $28.74 $30.95 $33.14 $35.34 Dividend
Discount Model Analysis Note: NPV = Net Present Value. Assumptions consistent with page 20. Current price to book value reflects BOW price as of July 29, 2026. Selected Companies includes AFG, ASIC, KNSL, MKL, PLMR, SKWD, RLI, WRB. Selected
Transactions includes acquisitions of specialty P&C insurers announced since the beginning of 2016 with deal values over $250M and less than $5B and one or more publicly available data points to calculate GAAP metrics. Reflects Bowhead
preliminary unaudited results for the six-month period ending June 30, 2026. NPV Sensitivity to Discount Rate and Terminal Book Value Multiple 7.5% 8.5% 9.5% 10.5% 11.5% Discount Rate Midpoint 2.25x terminal book value multiple
considers: The Selected Companies1 range of 2.17x – 3.57x The Selected Transactions2 range of 1.30x – 2.26x Bowhead's current book value multiple of 2.29x Implied Transaction book value multiple of 2.36x3 Page 21 PRIVATE AND CONFIDENTIAL
Premia Paid Analysis Page 21 PRIVATE AND CONFIDENTIAL
Announce Date Completion Date Buyer Name Target Name Target Ticker Offer Price
per Share Offer Price / 1-day Prior1 30-day VWAP2 TBD TBD American Family Mutual Insurance Company, S.I. Bowhead Specialty Holdings, Inc. BOW $34.00 6.4% 3 3 12.6% 03/19/25 06/26/26 The Doctors Company, an Interinsurance
Exchange ProAssurance Corporation PRA $25.00 58.8% 64.8% 11/06/25 TBD Aquarian Holdings, LLC Brighthouse Financial, Inc. BHF $70.00 35.1% 38.1% 08/27/25 02/24/26 Sompo Holdings, Inc. Aspen Insurance Holdings
Limited AHL $37.50 16.4% 20.8% 07/29/24 07/02/25 Sixth Street Partners, LLC Enstar Group Limited ESGR $338.00 (3.0%) 5.1% 10/09/23 07/09/24 Prosperity Life Group National Western Life Group,
Inc. NWLI $500.00 19.8% 11.5% 10/03/23 06/28/24 iA Financial Corporation Inc. Vericity, Inc. VERY $11.43 100.5% 102.9% 05/01/23 12/21/23 Antarctica Capital, LLC Midwest Holding
Inc. MDWT $27.00 97.4% 73.7% 02/08/23 11/16/23 Brookfield Reinsurance Ltd. Argo Group International Holdings, Ltd. ARGO $30.00 6.7% 11.7% 12/16/22 04/21/23 Altaris Capital Partners, LLC Trean Insurance Group,
Inc. TIG $6.15 97.1% 131.9% 03/21/22 10/19/22 Berkshire Hathaway Inc. Alleghany Corporation Y $848.02 25.3% 28.0% 08/09/21 05/25/22 Brookfield Asset Management Inc. American National Group,
Inc. ANAT $190.00 10.0% 24.1% Average Median 75th Percentile 25th Percentile 42.2% 25.3% 78.0% 13.2% 46.6% 28.0% 69.2% 16.2% Page 21 PRIVATE AND CONFIDENTIAL Premia Paid Analysis Includes transactions with 100% cash
consideration for publicly-traded insurance carriers on a US exchange with deal values over $100M in the last 5 years Note: Premia Paid Analysis not considered in fundamental valuation analysis but included for informational
purposes. Source(s): FactSet and SNL Financial. Includes property-casualty and life & annuity insurance carriers. Note: Premia calculated on a consistent basis for all transactions and are not adjusted for pre-announcement share-price
movements; as a result, transactions with meaningful share-price movement prior to announcement may reflect premiums that differ from those measured on a true unaffected basis. 1-day prior premiums reflect the offer price per share relative to
the target's closing price on the last trading day prior to announcement. Reflects the offer price per share relative to the target’s VWAP 30 calendar days ending the day prior to announcement. Market data as of July 29, 2026.
Appendix Page 21 PRIVATE AND CONFIDENTIAL
Source: Bowhead projections as adjusted by AmFam. Adjusted net income excludes,
from GAAP net income, net realized investment gains (losses), warrant expense, other non-operating costs, depreciation, note-redemption call premium, retention compensation, and amortization of acquisition-related intangibles and debt issuance
costs. operating adjustments are net of tax, and amortization of deal intangibles are pre-tax. See page 27 for bridge from GAAP net income. Net income and adjusted net income divided by 34,698,212 shares of Bowhead diluted common shares
outstanding; excludes AmFam Warrant, which is cancelled in connection with the Transaction, as directed by AmFam. Page 25 PRIVATE AND CONFIDENTIAL Dividends reflect target operating leverage of 1.5x net premium written to surplus as directed by
AmFam management. Historical operating leverage between 1.0x – 1.2x. GAAP Equity excluding purchase accounting adjustments as directed by AmFam. In millions, except per share data Years Ended December
31, 2026E 2027E 2028E 2029E 2030E 2031E Gross Written Premium $1,044.0 $1,187.7 $1,322.2 $1,444.0 $1,558.1 $1,658.2 Net Written Premium $627.4 $692.1 $771.7 $844.0 $911.6 $970.8 Income Statement Net Premium
Earned $586.8 $659.2 $731.3 $798.2 $874.0 $934.5 Net Investment Income $85.0 $111.7 $127.5 $148.1 $168.4 $188.0 Net Realized Gains (Losses) ($0.0) - - - - - Other Insurance Income $3.0 $2.8 $4.0 $9.2 $11.0 $12.4 Total
Revenue $674.8 $773.8 $862.9 $955.6 $1,053.3 $1,134.9 Expenses Net Loss and Loss Adj. Expenses $392.6 $454.9 $504.6 $550.8 $603.0 $644.8 Net Acquisition Expenses $59.8 $78.8 $99.1 $110.5 $122.2 $132.2 Operating
Expenses $108.2 $134.6 $132.7 $140.4 $140.0 $145.8 Underwriting Expenses $560.5 $668.3 $736.4 $801.7 $865.3 $922.8 Warrant Expense $3.1 $0.0 $0.0 $0.0 $0.0 $0.0 Interest and Financing
Fees $12.3 $12.3 $13.8 $9.0 $9.0 $9.0 Other Non-Operating Expenses $2.2 $18.3 $21.2 $17.2 $17.2 $17.2 Total Expenses $578.2 $698.9 $771.4 $827.8 $891.4 $949.0 Net Income $76.3 $58.9 $72.0 $100.7 $127.7 $146.6 Adjusted
Net Income (Non-GAAP)1 $78.8 $88.3 $95.0 $120.6 $141.1 $160.0 Diluted Adjusted EPS (Non-GAAP)2 $2.27 $2.55 $2.74 $3.48 $4.07 $4.61 Dividends3 - $200.6 $33.2 $65.6 $96.5 $121.1 Key Underwriting Ratios Loss
Ratio 66.9% 69.0% 69.0% 69.0% 69.0% 69.0% Expense Ratio 27.5% 33.1% 31.8% 30.8% 29.1% 28.7% Combined Ratio 94.4% 102.1% 100.8% 99.8% 98.1% 97.7% Balance Sheet Cash and
Investments $2,092.1 $2,305.9 $2,713.5 $3,118.5 $3,513.3 $3,891.7 Debt $147.2 $147.9 $150.0 $150.0 $150.0 $150.0 Total Equity4 $524.2 $353.1 $402.6 $448.3 $490.1 $526.2 Bowhead – Summary Projected Financial Results
Bowhead – Historical Non-GAAP Reconciliation Page 26 PRIVATE AND
CONFIDENTIAL Source: Company filings, earnings calls and Bowhead preliminary unaudited results pending auditor review ahead of Q2 earnings release. Adjusted net income is defined as net income excluding the impact of net realized investment
(losses) gains, non-operating expenses, foreign exchange losses (gains), and certain strategic initiatives. Adjusted net income excludes the impact of certain items that may not be indicative of underlying business trends, operating results, or
future outlook, net of tax impact. Bowhead calculates the tax impact only on adjustments that would be included in calculating Bowhead’s income tax expense using the estimated tax rate at which Bowhead received a deduction for these
adjustments. Interim (YTD) results are annualized. Diluted adjusted earnings per share is defined as adjusted net income divided by the weighted average common shares outstanding for the period, reflecting the dilution that may occur if
equity-based awards are converted into common stock equivalents as calculated using the treasury stock method. In millions, except per share data Years Ended December 31, Six Months Ended June
30, 2022A 2023A 2024A 2025A 2025A 2026A Adjusted Net Income Net Income (As Reported) $11.3 $25.0 $38.2 $53.8 $23.8 $32.1 Non-GAAP Adjustments Net Realized Investment Losses (Gains) - - $0.0 ($0.0) $0.0 $0.0 Non-Operating
Expenses - $0.6 $2.9 $2.3 $0.6 $0.0 Strategic Initiatives - $0.8 $2.7 - - - Tax Impact - ($0.3) ($1.2) ($0.5) ($0.1) ($0.0) Adjusted Net Income1 Adjusted Return On Equity Adjusted Net Income (Annualized)1,2 Average
Equity $11.3 $11.3 $85.9 $26.2 $26.2 $137.7 $42.7 $42.7 $281.3 $55.6 $55.6 $409.9 $24.2 $48.5 $389.1 $32.2 $64.4 $461.6 Adjusted Return On Equity 13.1% 19.0% 15.2% 13.6% 12.5% 13.9% Diluted Adjusted Earnings Per
Share Adjusted Net Income Diluted Wtd. Avg. Shares O/S $11.3 24.0 $26.2 24.0 $42.7 29.7 $55.6 33.7 $24.2 33.9 $32.2 33.5 Diluted Adjusted Earnings Per Share3 $0.47 $1.09 $1.44 $1.65 $0.72 $0.96
Note: Bowhead projections as adjusted by AmFam; AmFam adjustments reflect
non-recurring and non-operating expenses, consistent with historical calculation of adjusted net income. Adjusted net income excludes, from GAAP net income, net realized investment gains (losses), warrant expense, other non- operating costs,
depreciation, note-redemption call premium, retention compensation, and amortization of acquisition-related intangibles and debt issuance costs; operating adjustments are net of tax, and amortization of deal intangibles are pre-tax. GAAP Equity
excluding purchase accounting adjustments as directed by AmFam. Net income and adjusted net income divided by 34,698,212 shares of Bowhead diluted common shares outstanding; excludes AmFam Warrant, which is cancelled in connection with the
Transaction, as directed by AmFam. Page 26 PRIVATE AND CONFIDENTIAL Bowhead – Projection Non-GAAP Reconciliation In millions, except per share data Years Ended December 31, 2026E 2027E 2028E 2029E 2030E 2031E Adjusted Net Income Net
Income (As Projected) $76.3 $58.9 $72.0 $100.7 $127.7 $146.6 Historical Non-GAAP Adjustments: Net Realized Investment Gains (Losses) $0.0 - - - - - Warrant Expense $3.1 - - - - - Other Non-Operating
Costs - - - - - - AmFam Adjustments Call Premium To Redeem Notes - - $3.8 - - - Amortization Of Deal Intangibles - $16.9 $16.9 $16.9 $16.9 $16.9 Other One-Time Transaction Costs - $20.3 $8.3 $8.3 - - Tax
Impact ($0.7) ($7.8) ($6.1) ($5.3) ($3.6) ($3.6) Adjusted Net Income1 $78.8 $88.3 $95.0 $120.6 $141.1 $160.0 Adjusted Return On Average Equity Adjusted Net Income1 $78.8 $88.3 $95.0 $120.6 $141.1 $160.0 Average
Equity2 $486.1 $438.6 $377.8 $425.4 $469.2 $508.2 Adjusted Return On Average Equity 16.2% 20.1% 25.1% 28.4% 30.1% 31.5% Diluted Adjusted Earnings Per Share Adjusted Net Income1 $78.8 $88.3 $95.0 $120.6 $141.1 $160.0 Diluted
Weighted Average Shares Outstanding 34.7 34.7 34.7 34.7 34.7 34.7 Diluted Adjusted Earnings Per Share3 $2.27 $2.55 $2.74 $3.48 $4.07 $4.61
Source(s): FactSet, SNL Financial, company filings and Bowhead preliminary unaudited
results pending auditor review ahead of Q2 earnings release. Note: Results at or for the period ended March 31, 2026 except for WRB, KNSL, and RLI, which reflect results at or for the period ended June 30, 2026. Note: WACC = Weighted Average Cost
of Capital, CAPM = Capital Asset Pricing Model. Note: Medians, averages and quartiles exclude Bowhead Specialty Holdings Inc. (Current Trading). (1) 2-Year adjusted levered beta per FactSet as of July 29, 2026. (2) Not included in Medians,
averages or quartiles. (3) Reflects the median unlevered beta of peers most similar to Bowhead's profile (KNSL, PLMR, and SKWD), excluding both large, long-established public carriers and recently listed peers whose limited trading history
distorts measured beta. Historical long-term (1926-2026) market risk premium. U.S. 20-Year Treasury Rate as of July 29, 2026. Based on coupon rate of November 2025 senior note offering. Weighted Average Cost of Capital Calculation (in
millions) Duff & Phelps Size Premiums Decile Market Capitalization Smallest
Largest Size Premium 1 $53,677 $4,542,663 0.01% 2 $20,548 $53,648 0.27% 3 $10,784 $20,494 0.40% 4 $6,449 $10,708 0.37% 5 $4,237 $6,443 0.65% 6 $2,522 $4,232 0.88% 7 $1,472 $2,518 1.05% 8 $783 $1,472 0.77% 9 $351 $782 1.68% 10 $4 $351 4.37% WACC
Analysis Unlevered Beta 0.62 Debt / Equity 14.0% Levered Beta 0.69 Market Risk Premium4 5.00% Risk Free Rate5 5.21% Equity Size Premium 0.77% Corporate Tax Rate 21.0% Pre-Tax Cost of Debt6 7.75% Estimated Cost of
Equity 9.5% After-Tax Cost of Debt 6.1% Bowhead Estimated WACC 9.0% In millions, except per share data Company Ticker Price 7/29/2026 Market Cap. Total Debt Debt / Market Cap. Adjusted Levered Beta1 Unlevered Beta Equity Size
Premium CAPM Bowhead Specialty Holdings Inc. (Current Trading) 2 BOW $31.96 $1,050 $147 14.0% 0.56 0.51 0.77% 8.5% Selected Peers W. R. Berkley Corporation WRB $75.65 $29,385 $2,840 9.7% 0.43 0.40 0.27% 7.5% Markel Group
Inc. MKL $2,015.00 $25,215 $4,383 17.4% 0.72 0.63 0.27% 8.7% American Financial Group, Inc. AFG $143.51 $11,924 $1,820 15.3% 0.62 0.56 0.40% 8.4% Kinsale Capital Group,
Inc. KNSL $376.67 $8,580 $225 2.6% 0.64 0.62 0.37% 8.7% RLI Corp. RLI $65.65 $6,025 $297 4.9% 0.47 0.45 0.65% 8.1% Palomar Holdings, Inc. PLMR $142.91 $3,788 $297 7.9% 0.72 0.68 0.88% 9.5% Skyward Specialty Insurance
Group, Inc. SKWD $62.52 $2,535 $486 19.2% 0.69 0.60 0.88% 9.1% Ategrity Specialty Insurance Company Holdings ASIC $24.64 $1,184 $0 0.0% 0.39 0.39 0.77% 8.0% Average Median 75th Percentile 25th
Percentile 9.6% 8.8% 15.8% 4.4% 0.59 0.63 0.70 0.46 0.54 0.58 0.63 0.44 8.5% 8.5% 8.8% 8.1% High-growth, E&S-focused Median3 7.9% 0.69 0.62 9.1% Page 26 PRIVATE AND CONFIDENTIAL
Summary of Bowhead Research Coverage Source: FactSet, Bloomberg, Eikon and broker
research. Individual broker ratings have been conformed to a standardized Buy / Hold / Sell scale for comparability. Buy includes Outperform, Overweight, and Market Outperform; Hold includes Neutral, Equal-weight, and Market Perform. Date price
target was published. Market data as of July 29, 2026. EPS estimates reflect each broker's most recently publicly disclosed estimate as of July 29, 2026, shown on an adjusted diluted (operating) EPS basis. Dowling & Partners information
limited to estimates as access to research reports is restricted. Firm Name Research Analyst Name Stock Rating1 Price Target Date2 Price Target Premium to Current3 EPS4 2026E 2027E Keefe, Bruyette & Woods, Inc. Meyer
Shields Buy 07/07/26 $36.00 12.6% $2.00 $2.50 Citizens JMP Securities, LLC Matthew Carletti Buy 07/10/26 $35.00 9.5% $1.90 $2.35 Deutsche Bank Securities Inc. Cave Montazeri Buy 07/22/26 $31.00 (3.0%) $1.93 $2.33 Dowling
& Partners Securities, LLC 4 John Collins - - - - $1.85 $2.25 J.P. Morgan Securities LLC Pablo Singzon Hold 07/20/26 $33.00 3.3% $2.07 $2.57 Morgan Stanley & Co. LLC Bob
Huang Hold 07/06/26 $30.00 (6.1%) $2.00 $2.31 Piper Sandler & Co. Paul Newsome Buy 07/15/26 $36.00 12.6% $1.95 $2.40 RBC Capital Markets, LLC Rowland Mayor Buy 07/13/26 $38.00 18.9% $2.10 $2.45 Median 9.5% $1.98
$2.38 Average 6.8% $1.98 $2.40 Page 26 PRIVATE AND CONFIDENTIAL
