White Mountains Insurance Group, Ltd. · NYSE:WTM
White Mountains Insurance — Investor Presentation (June 2026)
86 slides from White Mountains Insurance's investor presentation, Jun 5, 2026
Slide 1: White Mountains Insurance Group 2026 Annual Investor Presentation
White Mountains Insurance Group, Ltd. 2026 Annual Investor Presentation Exhibit 99.1
Slide 2: Forward-Looking Statements
1 Forward-Looking Statements This presentation may contain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. All statements, other than statements of historical facts, included or referenced in this pr
Slide 3: Notes and Non-GAAP Financial Measures
2 Notes and Non-GAAP Financial Measures Notes The notes on p. 71-72 in the Appendices include additional context and information that management believes is helpful in understanding White Mountains's financial condition and performance. Non-GAAP Financial Measures Management believes the non-GAAP me
Slide 4: Introductions
Introductions
Slide 5: Board of Directors
4 Board of Directors Reid Campbell Peter Carlson Mary Choksi John Chu Liam Caffrey Philip Gelston Weston Hicks Suzanne Shank David Tanner Margaret Dillon
Slide 6: Thank You, Manning
5 Thank You, Manning Retired at year end after 21 years at WTM CEO and Board member from 2017 to 2025 Led period of stellar value creation – (A)BVPS [1] grew by 13% per year – MVPS grew by 12% per year – $3.5 billion of capital deployed – $2.3 billion returned to shareholders Valued mentor a
Slide 7: What We Care About Is Not Changing
6 What We Care About Is Not Changing Track record of 40+ years as a public company Objective is to compound per share values over long periods of time Operating principles remain unchanged: – Underwriting comes first – Maintain a disciplined balance sheet – Invest for total return – Think like
Slide 8: Year in Review
Year in Review
Slide 9: 2025 Year in Review
8 2025 Year in Review Excellent 2025 one of our best years on record – Grew BVPS by 25% to $2,188 Key highlights: – Majority sale of Bamboo – Good operating results – Solid absolute investment returns, although total return lagged benchmarks – $430+ million of new deployments Distinguished,
Slide 10: Returns in Context
9 Returns in Context YTD May 31, Book value returns 2025 1Q26 Market value returns 2025 2026 WTM 25.4% -0.8% WTM 6.9% -0.6% Beginning-of-year 10YT + 700 bps [2] 11.6% 11.2% S&P 500 17.9% 11.3% Dowling & Partners Composite TVC [3] 26.1% n/a S&P Financials 14.9% -6.0% Dowling & Partners Composite [4]
Slide 11: Sale of Bamboo: Thank You to the Team
10 Sale of Bamboo [5]: Thank You to the Team In December, closed sale to CVC Capital Transaction valued Bamboo at $1.75 billion Crystallized substantial value in a short period with continuing upside “deal you don’t refuse” – $0.3 billion of equity capital invested $1 billion of cash retur
Slide 12: Deployments, Distributions and Undeployed Capital
11 $3.1 $0.2 $1.6 $0.3 $1.1 $0.8 $0.0 $0.5 $1.0 $1.5 $2.0 $2.5 $3.0 $3.5 $4.0 1Q17 1Q22 2Q22 2Q25 3Q25 1Q26 $ in b ill io ns Capital deployments Capital distributions Undeployed capital Deployments, Distributions and Undeployed Capital [6] Post-OneBeacon, Sirius & Symetra $1.8 billion deployed $1.5
Slide 13: Recent Deployments
12 Recent Deployments Description Capital deployed ($ in millions) CompanyYear 2025 Insurance brokerage platform $150 Specialty P&C MGA and program manager225 Electrical contracting services 58 $433Total 2026 Diversified MGA platform$125 Low-voltage electrical systems integrator97 Electrical contrac
Slide 14: Deployment Themes
13 Deployment Themes Seeing good deal flow, but this is a challenging deployment environment in the (re)insurance sector Patience required; circumstances change quickly Where we have had success: – Differentiated platforms with partners and management teams we know and trust – Proprietary tran
Slide 15: Capital & Financial Position
Capital & Financial Position
Slide 16: Financial Position as of 1Q26
15 Financial Position as of 1Q26 Total capital of $7.0 billion No financial leverage at parent – $250 million undrawn revolver Prudent financial leverage at operating businesses Consolidated debt to total capital of 12% Undeployed capital of $0.8 billion 14% of WTM equity
Slide 17: Owners' Capital Per Share as of 1Q26
16 Owners’ Capital Per Share as of 1Q26 [7] Total: $2,170 BVPS Ark 21% WM Outrigger 2% Kudu 16% HG Global 14% Distinguished 4% Bamboo 5% BroadStreet 3% PassportCard / DavidShield 3% MediaAlpha 3% Bishop Street 2% White Mountains Partners 4% Other operating businesses 3% Strategic investments & other
Slide 18: Key Operating Businesses
17 Key Operating Businesses Per Share [7] ($) Owners’ Capital [7] ($ in millions) Management ownership [8] WTM ownership [8] Initial investment year Company $483$1,19537%63%2021 34685615%78%2018 3107673%97%2012 8621425%44%2025 10526026%15%2024 69170n/a<5%2025 6917048%52%2015 67166n/a28%2014 50125n/a
Slide 19: Operating Businesses
Operating Businesses
Slide 20: Ark: Overview
19 Ark: Overview Specialized P&C (re)insurance business founded in 2007 by Ian Beaton and Nick Bonnar Underwrites five major lines of business: property, specialty, marine & energy, casualty and A&H Business written via: – Lloyd’s Syndicates 4020 and 3902 and ACSN 3832 – Bermuda-based reinsure
Slide 21: Ark: Financial Snapshot
20 $598 $1,059 $1,452 $1,898 $2,207 $2,557 $2,541 98% 87% 82% 82% 83% 83% 82% 0% 10% 20% 30% 40% 50% 60% 70% 80% 90% 100% $0 $500 $1,000 $1,500 $2,000 $2,500 $3,000 $3,500 2020 2021 2022 2023 2024 2025 1Q26 TTM C om bined R atio G ro ss W rit te n P re m iu m s ($ in m ill io ns ) Property Specialty
Slide 22: Ark: Recent Results
21 Ark: Recent Results Excellent 2025 – Combined ratio of 83% – Grew Tangible Book Value by 28% to $1.7 billion; 24% CAGR since our acquisition – Gross written premiums of $2.6 billion, up 16% YOY and over 4x since our acquisition Good start in 1Q26 – Combined ratio of 91% – Gross written premiu
Slide 23: Ark: Outrigger
22 Ark: Outrigger Outrigger Re is a sidecar to Ark’s Bermuda global property cat XOL reinsurance book – Ark launched Outrigger for the 2023 underwriting year; has renewed annually – Franchise value to Ark through expanded portfolio footprint and fee income Excellent results to date for WTM – $16
Slide 24: Ark: Relative Performance at Lloyd's
23 Ark: Relative Performance at Lloyd’s WM Outrigger 2021-2025 Profitability and Volatility [11] Less Profitable More Profitable L es s V ol at ile M or e V ol at ile Source: Insurance Insider ERS 218 Arch 1955 Antares 1274 CNA Hardy 382 RenRe 1458 Canopius 4444 Brit 2987 Argenta 2121 Liberty 4472 T
Slide 25: Ark: Market Environment
24 Ark: Market Environment WM Outrigger Rate, Terms & Conditions Uncertainties Property (re)insurance softening fast; profitability adequate, but worrying signs Specialty differentiated Marine & energy softening, but impact of Baltimore bridge loss yet to be realized Casualty up 5-10%
Slide 26: Ark: Going Forward
25 Ark: Going Forward WM Outrigger Near-term significant slowdown in growth but some opportunities too Mid-term return to cyclical softening Structural market changes will drive differences broker dynamics, MGA growth and AI Continued new opportunities yacht, fine art & specie and se
Slide 27: Kudu: Overview
26 Kudu: Overview Provides capital solutions and strategic advice to asset and wealth managers Deals typically structured as revenue shares with equity participation rights – Healthy cash yield at inception (~9% on average) – Growing cash yield with growth in AUM – Equity kicker from portfolio c
Slide 28: Kudu: WTM Perspectives on the Business
27 Kudu: WTM Perspectives on the Business 1. Fee-generating “GP stakes” business – Recurring / growing revenue and EBITDA stream – Proven model and management team to continually deploy/harvest capital; creates franchise value – Primary metrics are Annualized Adjusted EBITDA and Levered Return; gene
Slide 29: Kudu: Recent Results
28 Kudu: Recent Results Good 2025 results – GAAP ROE of 13% with portfolio value up 8% on a same store basis – Annualized Adjusted EBITDA of $70 million; Levered Return of 9% – Deployed $197 million [12] into 3 new deals Solid start to 2026 – TTM GAAP ROE of 12% with portfolio value up 3% QOQ on
Slide 30: Kudu: Financial Snapshot
29 Kudu: Financial Snapshot $401 $670 $696 $896 $1,014 $1,291 $1,359 $29 $48 $39 $66 $61 $70 $69 $0 $10 $20 $30 $40 $50 $60 $70 $0 $200 $400 $600 $800 $1,000 $1,200 $1,400 $1,600 $1,800 2020 2021 2022 2023 2024 2025 1Q26 TTM A nnualized A djusted E B IT D A G A A P F ai r V al ue o f Po rt fo lio ($
Slide 31: Kudu: Returns
30 8% 11% 8% 12% 9% 9% 9% 7% 20% 12% 17% 9% 13% 12% 0% 2% 4% 6% 8% 10% 12% 14% 16% 18% 20% 2020 2021 2022 2023 2024 2025 1Q26 TTM R et ur ns Levered Return GAAP ROE Kudu: Returns Average = 13% Average = 9%
Slide 32: Kudu: Portfolio Composition
31 Real assets 27% CLOs 20%Energy 16% Specialty finance 12% Tech/software 8% Financials 5% Industrials 4% Healthcare 4% Commodities / trade finance 3% Private capital 44% Wealth management 27% Liquid alternatives 24% Traditional 5% Kudu: Portfolio Composition [13] By Manager Format By Asset Class Pr
Slide 33: Kudu: Strategic Priorities
32 Kudu: Strategic Priorities Maintain focus on the lower middle market of the asset and wealth management industry – Build upon success in partnering with specialized boutiques with positive momentum Expand our platform identify key markets with favorable macro trends and attractive competiti
Slide 34: HG Global: Overview
33 HG Global: Overview BAM is a mutual company that insures essential public purpose municipal bonds; owned by policyholders – Primary market – Secondary market HG Global is a stock company owned by WTM – Provides first-loss reinsurance to BAM – Provided startup capital to BAM in the form of sur
Slide 35: HG Global: Recent Results
34 HG Global: Recent Results Strong 2025 for BAM – Total premiums [14] of $160 million (up 18% YOY), a record year – Par insured [14] of $21 billion (up 7% YOY) – Total pricing [14] at 76 bps (up 10% YOY) – Cash payments on surplus notes of $35 million Mixed 2025 for HG Global – Solid underwriti
Slide 36: HG Global: Debt Refinancing
35 HG Global: Debt Refinancing In May, HG Global refinanced its existing senior debt facility – $200 million principal (upsized from $150 million) – Private placement with a syndicate of six blue chip credit investors – Investment grade (BBB) rating affirmed Significant improvement in terms vs.
Slide 37: BAM: Financial Highlights & Market Environment
36 BAM: Financial Highlights & Market Environment Year ended TTM ($ in billions, except where stated) 2023 2024 2025 1Q26 Total new municipal bond issuance 363$ 496$ 572$ 585$ Par insured [14] 15.6$ 19.7$ 21.1$ 21.8$ Total pricing [14] 84 bps 69 bps 76 bps 75 bps Total premiums ($ in millions) [14]
Slide 38: HG Global: Financial Snapshot
37 HG Global: Financial Snapshot Year ended TTM ($ in millions) 2023 2024 2025 1Q26 Growth in book value [15] 9% -6% 4% 2% Normalized Growth in Book Value 6% 7% 8% 8% Par value assumed 2,356$ 2,952$ 3,170$ 3,260$ Total pricing 213 bps 177 bps 194 bps 193 bps Gross written premiums 50$ 52$ 61$ 63$ In
Slide 39: HG Global: Strategic Priorities
38 HG Global: Strategic Priorities #1 priority remains to improve HG Global’s running return and contribution to WTM BVPS growth Recent actions taken: – Refinanced debt to improve levered return and cash flow – Enhanced investment return profile within regulatory and rating agency constraints
Slide 40: Distinguished Programs: Overview
39 Distinguished Programs: Overview Full-service specialty MGA and program manager with 30+ year operating track record Operates via two distinct verticals: – ScaleCo established programs, historical focus on excess casualty, real estate and hospitality sectors – GrowthCo diversified portfol
Slide 41: Distinguished: Recent Results
40 Distinguished: Recent Results Solid results in 2025 – Managed premiums [17] of $568 million (up 6% YOY) – ScaleCo Adjusted EBITDA [17] of $26 million (up 7% YOY) – Continued positive momentum at GrowthCo 3 new launches – Executed accretive sale of non-core Prize program Flattish start to 20
Slide 42: Distinguished: Company Strategy
41 Distinguished: Company Strategy Establish a scalable framework to attract, incentivize and retain top underwriters/books from carriers Unified shared services platform supporting integrated business variety of services to help programs thrive Work with a select number of highly rated carr
Slide 43: Distinguished: Financial Snapshot
42 $320 $424 $534 $568 $576 $18 $25 $25 $26 $26 $0 $5 $10 $15 $20 $25 $30 $35 $40 $45 $50 $0 $100 $200 $300 $400 $500 $600 $700 2022 2023 2024 2025 1Q26 TTM ScaleC o A djusted E B IT D A ($ in m illions) M an ag ed p re m iu m s ($ in m ill io ns ) Managed premiums ScaleCo Adjusted EBITDA Distinguis
Slide 44: Distinguished: GrowthCo Acqui-hire Strategy
43 Distinguished: GrowthCo “Acqui-hire” Strategy GrowthCo acquires top underwriting talent through an “acqui-hire” approach – Broaden specialty lines offerings and diversify carrier capacity greater market resilience overall Target underwriting talent/teams with: – Ability to generate ~$50+ mi
Slide 45: Bamboo: Overview
44 Bamboo: Overview Homeowners’ insurance MGA founded and led by John Chu Strategically launched in California and Texas; expect to expand to other markets Differentiated model with near and long-term competitive advantages: – Commission-based MGA model with blue-chip distribution and reinsura
Slide 46: Bamboo: Recent Results
45 Bamboo: Recent Results Excellent 2025 – Performed well for policyholders and capital providers through California wildfires – Managed premiums [18] of $766 million (up 58% YOY) – MGA Adjusted EBITDA of $106 million (up 2x YOY) Off to a great start in 2026 – Continued strong growth in managed
Slide 47: Bamboo: Financial Snapshot
46 Bamboo: Financial Snapshot $215 $484 $766 $7 $53 $106 $0 $15 $30 $45 $60 $75 $90 $105 $120 $0 $100 $200 $300 $400 $500 $600 $700 $800 2023 2024 2025 M G A A djusted E B IT D A ($ in m illions)M an ag ed p re m iu m s[1 8] ($ in m ill io ns ) Managed premiums, renewal Managed premiums, new MGA Adj
Slide 48: Bamboo: Growth Plan
47 Bamboo: Growth Plan Continue to expand in California – Legacy carriers still exiting or limiting business – Defensive moat via strong program partner relationships Expand into new states entered Texas in September 2025 Expand distribution via national carrier and agent network and digital
Slide 49: BroadStreet Partners: Overview
48 BroadStreet Partners: Overview Leading insurance brokerage platform across US and Canada Diversified, commission and fee-based economic model Platform with strong, 25-year operating track record and proven M&A strategy Top-tier management team led by Mike O'Connor (former Co-President of
Slide 50: BroadStreet Partners: Unique Co-Ownership Model
49 BroadStreet Partners: Unique Co-Ownership Model M&A Organic growth Operating capabilities 31 Core agency partners 600+ tuck-in acquisitions since inception Diversified business with sustainable organic growth across cycles Variety of levers to accelerate growth vs. underlying industry (e.
Slide 51: BroadStreet Partners: Recent Results
50 BroadStreet Partners: Recent Results Solid 2025 – Generated total revenue of $2.5 billion – Good operating performance with mid-single digit organic growth, in line with peers – Continued execution on accretive M&A strategy 69 total deals completed – Rolled several Core agency CEOs into Broad
Slide 52: PassportCard / DavidShield: Overview
51 PassportCard / DavidShield: Overview Offers travel and expat medical insurance Delivers coverage and services in 180+ countries around the world Real-time, paperless insurance solution, delivered via debit card Superior customer experience, premium pricing and high reactivation rates Or
Slide 53: PassportCard / DavidShield: 2025 Results
52 PassportCard / DavidShield: 2025 Results [19] Core premiums of $262 million (up 24% YOY) – Israeli leisure travel premiums of $148 million (up 38% YOY) – Expat medical premiums of $114 million (up 9% YOY) Core EBITDA of $7 million (up 17% YOY but well below pre-2023 levels) – Impacted by war
Slide 54: PassportCard / DavidShield: 2026 Results
53 PassportCard / DavidShield: 2026 Results [19] Challenging 1Q26 as war in the Middle East once again impacted the Israeli leisure travel business TTM core premiums of $259 million, down 1% QOQ – After record start, Israeli leisure travel premiums declined significantly in March (at 30% of plan
Slide 55: PassportCard / DavidShield: Financial Snapshot
54 PassportCard / DavidShield: Financial Snapshot [19] COVID-19 Wars in Middle East $154 $75 $125 $232 $217 $212 $262 $259 $0 $40 $80 $120 $160 $200 $240 $280 2019 2020 2021 2022 2023 2024 2025 1Q26 TTM C or e C on tr ol le d P re m iu m s ($ in m ill io ns ) Leisure travel - Israel Expat medical -
Slide 56: MediaAlpha: Overview
55 MediaAlpha: Overview Online customer acquisition technology company (NYSE: MAX) Industry-leading marketplaces for real-time transactions in clicks, calls and leads Multiple verticals, including P&C, health and life insurance Fee-based economic model: takes percentage on all marketplace tr
Slide 57: MediaAlpha: WTM MOIC Returns to Date
56 MediaAlpha: WTM MOIC Returns to Date [20] 8.9x 1.5x 3.5x 0.1x 12.4x 1.7x 0.0x 2.0x 4.0x 6.0x 8.0x 10.0x 12.0x 14.0x Original investment (2014) Tender offer (2023) W T M M O IC (a s of 3 /3 1/ 20 26 ) WTM MOIC, cash received WTM MOIC, remaining MAX shares $46 million $59 million
Slide 58: MediaAlpha: Recent Results
57 MediaAlpha: Recent Results Mixed year in 2025 record operating results but lagging stock price – Revenues of $1.1 billion (up 29% YOY) – Adjusted EBITDA of $114 million (up 18% YOY) – Settled FTC matter pertaining to under-65 health business – Launched $50 million share buyback program (upsiz
Slide 59: MediaAlpha: Financial Snapshot
58 MediaAlpha: Financial Snapshot $585 $645 $459 $388 $865 $1,114 $1,159 $0 $30 $60 $90 $120 $150 $0 $200 $400 $600 $800 $1,000 $1,200 2020 2021 2022 2023 2024 2025 1Q26 TTM A djusted E B IT D A ($ in m illions) R ev en ue ($ in m ill io ns ) Revenue - p&c Revenue - health Revenue - life & other Adj
Slide 60: Bishop Street: Overview
59 Bishop Street: Overview In February, we closed a $125 million structured investment in Bishop Street Underwriters Diversified MGA platform with $650+ million of managed premium, majority-owned by RedBird Capital Bilateral deal; long-standing relationships with management and RedBird Oppor
Slide 61: White Mountains Partners: Overview
60 White Mountains Partners: Overview Wholly-owned business unit launched in 4Q23 Led by CEO and Managing Partner, John Daly Provides first institutional capital to family, founder and entrepreneur-owned businesses in three sectors: – Essential services – Light industrial – Specialty consumer
Slide 62: White Mountains Partners: Progress & Outlook
61 White Mountains Partners: Progress & Outlook Deployed roughly $200 million of equity capital to date across 3 deals: – Enterprise Solutions (April 2025) electrical contracting services – BaseSix (April 2026) low-voltage electrical systems integrator – Hawkeye (May 2026) electrical contrac
Slide 63: Investments
Investments
Slide 64: Investments: Philosophy and Approach
63 Investments: Philosophy and Approach Invest for total return Policyholder funds invested conservatively; shareholder funds invested more aggressively Relative to insurance peers, we tend to have (i) shorter duration and (ii) higher equity exposure Parent investment decisions take into acc
Slide 65: Investments: Composition
64 Investments: Composition ($ in millions) Ark HG Global Parent Consolidated Fixed Income 3,206$ 755$ 763$ 4,725$ Equities and Alternatives 620 - 426 1,045 Total Portfolio 3,826$ 755$ 1,189$ 5,770$ Investment Leverage 2.5x 1.4x 1.0x 1.1x Fixed income portfolio duration (years) 1.1 4.2 1.6 1.7 Fixed
Slide 66: Investments: Performance
65 Investments: Performance * Driven primarily by (i) lower relative market neutral and alternative results and (ii) timing of ETF trading activity to support corporate needs. 2023 to 1Q26 Quarter 2023 to Annualized Year ended ended 1Q26 Relative ($ in millions) 2023 2024 2025 1Q26 Annualized Perfor
Slide 67: What to Expect
What to Expect
Slide 68: What to Expect from Us
67 What to Expect from Us More of the same Focused on growing per share values over long periods of time; comfortable with lumpy return profile Not focused on near-term GAAP results Adhering to our core operating principles: – Underwriting comes first – Maintain a disciplined balance sheet –
Slide 69: Wise Words…
68 Wise Words… 1-year 5-year 10-year 20-year Since WTM IPO (1985) WTM - (A)BVPS [1] 23.9% 13.0% 12.5% 10.1% 13.5% WTM - MVPS 14.1% 14.6% 10.7% 7.1% 12.3% S&P 500 17.8% 12.1% 14.2% 10.5% 11.5% S&P P&C Insurance Total Return [22] -4.1% 16.8% 14.7% 10.7% 10.5% Return periods ended March 31, 2026
Slide 70: Superior Track Record Over 40+ Years
69 Superior Track Record Over 40+ Years $20 $75 $280 $1,050 Year 1990 1995 2000 2005 2010 2015 2020 Book Value Per Share * Market Value Per Share * Growth since IPO: Book Value Per Share 13% annualized, including dividends Market Value Per Share 12% annualized, including dividends Black Monday Finan
Slide 71: Appendices
Appendices 1. Notes (p. 71) 2. Non-GAAP Financial Measures (p. 73)
Slide 72: Notes
71 Notes 1. WTM book value returns reflect growth in Adjusted Book Value Per Share through 2024 and book value per share beginning in 1Q25, both including dividends. 2. Beginning-of-year yield on 10-year U.S. Treasury plus 700 bps, which has been WTM’s return target for many years. 3. Dowling & Part
Slide 73: Notes
72 Notes 14. BAM’s premiums, par insured and total pricing include gross written premiums, member surplus contributions collected and the present value of installment premiums; each excludes deals not reinsured by HG Re. 15. HG Global’s book value reflects WTM’s interest in HG Global’s book value af
Slide 74: Non-GAAP Measures: GAAP BVPS vs ABVPS Returns
73 Non-GAAP Measures Comparison of WTM's GAAP BVPS returns to ABVPS returns 2017 - 2025 Rountree CEO tenure 5-year 10-year 20-year Since WTM IPO (1985) WTM - BVPS 12.2% 12.1% 12.1% 9.9% 13.3% WTM - (A)BVPS 12.7% 13.0% 12.5% 10.1% 13.5% Return periods ended March 31, 2026 WTM book value returns refle
Slide 75: Non-GAAP Measures: Owners' Capital Reconciliation
74 Non-GAAP Measures Reconciliation of WTM's GAAP book value and GAAP BVPS to Owners' Capital and Owners' Capital Per Share ($ millions, except per share amounts) 1Q26 Owners' Capital GAAP Book Value Adjustments[a] Owners' Capital GAAP Book Value ($) Owners' Capital ($) Owners' Capital (%) Ark 1,099
Slide 76: Non-GAAP Measures: Ark Tangible Book Value
75 Non-GAAP Measures Reconciliation of Ark's GAAP equity to Tangible Book Value and calculations of (i) growth in book value to Growth in Tangible Book Value, including dividends and (ii) the 5-year CAGR of book value and Tangible Book Value, including dividends ($ millions) As of January 1, 2021 As
Slide 77: Non-GAAP Measures: Kudu Adjusted EBITDA and Levered Return
76 Non-GAAP Measures Reconciliations of Kudu's GAAP net income to Annualized Adjusted EBITDA and return on equity to Levered Return Year ended TTM ($ millions) 2020 2021 2022 2023 2024 2025 1Q26 GAAP net income (loss) [a] 21$ 78$ 62$ 105$ 65$ 115$ 112$ Add back: Interest expense 6 12 15 21 22 26 27
Slide 78: Non-GAAP Measures: HG Global Normalized Growth in Book Value
77 Non-GAAP Measures Reconciliation of WTM's interest in HG Global's growth in GAAP book value to Normalized Growth in Book Value Year ended TTM ($ millions) 2023 2024 2025 1Q26 Beginning WTM interest in HG Global [a] 712$ 779$ 729$ 752$ Ending WTM interest in HG Global 779 729 756 767 Change in WTM
Slide 79: Non-GAAP Measures: Bamboo MGA Adjusted EBITDA
78 Non-GAAP Measures Reconciliations of Bamboo's GAAP net income to MGA Adjusted EBITDA ($ millions) 2024 GAAP net income (loss) 26$ Exclude: Net (income) loss, Bamboo Captive (1) MGA net income (loss) 25 Add back: Interest expense - Income tax expense (benefit) 7 Depreciation expense 0 Amortization
Slide 80: Non-GAAP Measures: WTM Fixed Income and Equities and Alternatives
79 Non-GAAP Measures Reconciliation of WTM's (i) GAAP fixed maturity and short-term investments to Fixed Income (ii) GAAP common equity securities, investment in MediaAlpha and other long-term investments to Equities and Alternatives and (iii) Equities and Alternatives / Total Portfolio Total Portfo
Slide 81: Non-GAAP Measures: Ark Investment Reconciliation
80 Non-GAAP Measures Reconciliation of Ark's (i) GAAP fixed maturity and short-term investments to Fixed Income, (ii) GAAP common equity securities and other long-term investments to Equities and Alternatives (iii) Equities and Alternatives / Total Portfolio and (iv) Equities and Alternatives / Shar
Slide 82: Non-GAAP Measures: HG Global Fixed Income
81 Non-GAAP Measures Reconciliation of HG Global's GAAP fixed maturity and short-term investments to Fixed Income HG Global's Total Portfolio equals its Fixed Income portfolio. ($ millions) 1Q26 GAAP fixed maturity and short-term investments 791$ Remove: certain short-term investments (39) Add: accr
Slide 83: Non-GAAP Measures: Other Operations Parent Investments
82 Non-GAAP Measures Reconciliation of Other Operations's (i) GAAP fixed maturity and short-term investments to Parent Fixed Income (ii) GAAP common equity securities, investment in MediaAlpha and other long-term investments to Parent Equities and Alternatives and (iii) Parent Equities and Alternati
Slide 84: Non-GAAP Measures: Investment Leverage
83 Non-GAAP Measures Reconciliation of GAAP portfolio leverage to Investment Leverage for (i) Ark, (ii) Kudu & Other, (iii) HG Global, (iv) Distinguished, (v) Parent and (vi) White Mountains Consolidated ($ millions) Investment Leverage: Ark Kudu & Other HG Global Distinguished Parent Consolidated N
Slide 85: Non-GAAP Measures: Equities and Alternatives / Adjusted Equity
84 Non-GAAP Measures Reconciliation of WTM's (i) GAAP common equity securities, investment in MediaAlpha and other long-term investments to Equities and Alternatives and (ii) Equities and Alternatives / Adjusted Shareholders Equity ($ millions) 1Q26 Numerator GAAP common equity securities, investmen
Slide 86: Non-GAAP Measures: Total Portfolio Return Reconciliation
85 Non-GAAP Measures Reconciliation of WTM's GAAP investment returns to Total Portfolio Return, Fixed Income Return and Equity and Alternative Return Year ended Quarter ended 2023 to 1Q26 (returns in USD) 2023 2024 2025 1Q26 Annualized GAAP total return on investment portfolio 11.4% 6.9% 9.1% 0.2% 8
White Mountains Insurance Group — Investor Presentation (June 2026) on 6ix