White Mountains Insurance Group, Ltd. · NYSE:WTM

White Mountains Insurance — Investor Day (June 2014)

45 slides from White Mountains Insurance's investor day presentation, Jun 10, 2014

1. Slide 1: White Mountains Annual Investor Meeting June 10, 2014

   White Mountains Insurance Group, Ltd. Annual Investor Meeting June 10, 2014 Exhibit 99.1

2. Slide 2: Forward-Looking Statements

   2 Forward-Looking Statements This presentation contains, and management may make, certain statements that are not historical facts but that are 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 state

3. Slide 3: White Mountains Annual Investor Meeting

   3 White Mountains Annual Investor Meeting Ray Barrette:  Introduction and Highlights  Allocation of Capital  HG Global/BAM Allan Waters:  Sirius Group Manning Rountree:  Insurance Services  Investments David Foy:  Share Repurchases  Capital Ray Barrette:  Final Comments and Q&A

4. Slide 4: WTM - Solid Performance in 2013 and So Far in 2014

   WTM - Solid Performance in 2013 and So Far in 2014 4 2013 1Q14 White Mountains Growth in ABVPS 9.5% 2.2% Investments Total Return 5.2% 1.3% OneBeacon Growth in BVPS 17.3% 4.2% Combined ratio 92.4% 88.8% Sirius Group Growth in ABV 11.3% 3.8% Combined ratio 82.1% 73.3%

5. Slide 5: WTM - Solid Performance in 2013 and So Far in 2014

   WTM - Solid Performance in 2013 and So Far in 2014  HG Global/BAM executed well in tough environment:  Cumulative par insured = $6 billion at 1Q14 (700 members)  54% market share of insured deals in 1Q14 (48% of par insured)  Strong trading value  Insurance Services Businesses:  Insurance mark

6. Slide 6: WTM – Allocation of Equity Capital

   WTM – Allocation of Equity Capital ($ in billions) 6 Sirius Group, excluding Symetra 1.2$ OneBeacon 0.9 HG Global/BAM 0.6 Symetra 0.4 Insurance Services 0.1 Parent/Other 0.9 4.0$

7. Slide 7: WTM – Our Track Record Since IPO

   WTM – Our Track Record 7 Since WTM (growth including dividends) 1-year 3-year 5-year 7-year 10-year IPO White Mountains - ABVPS 10% 14% 13% 7% 9% 15% S&P 500 32% 16% 18% 6% 7% 11% Berkshire Hathaway - BVPS 18% 12% 14% 10% 10% 17% Return Period Ended December 31, 2013

8. Slide 8: HG Global/BAM

   HG Global/BAM 8

9. Slide 9: HG Global/BAM – Great Execution in a Tough Environment

   HG Global/BAM – Great Execution in a Tough Environment 2012-2013:  Funded HG Global/BAM in July 2012  BAM is the leader in its target market:  Strong team, systems and risk management  Licensed in all 50 states and DC  Significant market position with broad range of dealers/issuers 1Q14:  Cumu

10. Slide 10: HG Global/BAM – Market Deterioration since 2012

    HG Global/BAM – Market Deterioration since 2012  Lower new issue volume:  $350B $275B  Tighter spreads on low interest rates  Low but improving insured penetration  Severe price competition 10

11. Slide 11: HG Global/BAM - The Capital Advantage

    PRIVATE CAPITAL MUTUAL CAPITAL Time HG Global/BAM - The Capital Advantage 11 4-6% RoC (5-7% S&P RAP) WTM economics derived from:  Interest on surplus notes  Repayment of surplus notes  Reinsurance premiums and float  Long-term franchise value 2-4% RoC 10-15% RoC Surplus Note Repayment

12. Slide 12: HG Global/BAM – Pricing

    HG Global/BAM – Pricing  Competition limits the share of available market spreads captured by bond insurers  Expect “Capture %” to increase when volume and interest rates increase: 12 1Q14 Credit spread 15 bps 15 bps 22 bps Capture % 37% 50% 50% Annual cost 5.6 bps 7.5 bps 11.0 bps Upfront premium

13. Slide 13: HG Global/BAM – Secondary Market Opportunity

    HG Global/BAM – Secondary Market Opportunity  Secondary market trades demonstrate that BAM adds significantly more value than it currently captures in the primary market:  15-30 bps for “A” rated bonds versus uninsured  25-40 bps for “BBB” rated bonds versus uninsured  Secondary market offers be

14. Slide 14: HG Global/BAM – Built to Last

    HG Global/BAM -–- BUILT TO LAST  Current environment:  Credit quality is on target  Market share is high  Pricing is below target  Competition is severe  Drivers of further success are:  Higher interest rates (“magic” 5% muni rate at retail)  Higher new issue volume  Better insured penetrat

15. Slide 15: Sirius Group

    Sirius Group 15

16. Slide 16: Sirius Group – Strong Current Results

    16 Sirius Group – Strong Current Results 2013:  ABV grew 11.3%, including dividends  82% combined ratio:  $85 million (10 pts) of catastrophe losses  5% decline in gross written premiums to $1.1 billion:  19% reduction in A&H writings to $271 million  4% increase in property premiums to $637 m

17. Slide 17: Sirius Group – Long-Term Improvement

    17 Sirius Group – Long-Term Improvement

18. Slide 18: Sirius International - Göran Thorstensson's Record

    18 Sirius International - Göran Thorstensson’s Record Legend: Notes: * Excludes reinsurance with affiliates. Includes Sirius America from 2012 forward. ** Per S&P. 60% 70% 80% 90% 100% 110% 120% 130% 60% 70% 80% 90% 100% 110% 120% 130% 1993 1998 2003 2008 2013 Co mb in ed R ati o Sirius Internationa

19. Slide 19: Sirius Group – Why We Are Different

     Focus on local and regional companies:  Over 5,000 treaties and over 3,800 direct/facultative  Long-term partnerships with clients: 19 Sirius Group – Why We Are Different ($ in millions) 20 years or more 350$ 31% 10-20 years 322 29% Less than 10 years 448 40% Total 1,120$ 100% 2013 Gross Premium

20. Slide 20: Sirius Group - 2014 Outlook

    20 Sirius Group - 2014 Outlook  Increasing competition across most territories and lines:  Growing excess capacity – traditional & capital markets  Sirius Group’s book is well-positioned relative to peers  Maintaining underwriting discipline  All writings remain adequately priced or better  Pe

21. Slide 21: Insurance Services

    Insurance Services 21

22. Slide 22: Insurance Services – A Growing Focus

    Insurance Services – A Growing Focus  Pivot from “traditional” balance sheet transactions  Focus on new / emerging areas:  Low capital  High potential  Thematic investments:  Price comparison  Insurance technology  Specialization  Global reach  Progress to date:  8 deals  $150 million ca

23. Slide 23: Insurance Services - Deals to Date

    Insurance Services - Deals to Date 23 Theme Investment Domicile Commitment ($ in millions) 1. Global Price Comparison: Inspop/CompareNow United States $20 TaCerto Brazil 3 Wobi Israel 8 2. Insurance Technology: QuoteLab United States 36 PassportCard Israel/International 21 Valen United States 2 3. S

24. Slide 24: QuoteLab – A Game Changing Solution

    QuoteLab – A Game Changing Solution  Advertising technology business, with focus on insurance:  Auto  Life & health  Expansion to new verticals  WTM acquired 60% interest in March:  Paid cash plus an earn-out tied to gross profit  Founders retain 40% interest  “MediaAlpha Exchange” => superi

25. Slide 25: Wobi – A Local Market Breakthrough

    Wobi – A Local Market Breakthrough  Israeli price comparison / online agency business:  Auto  Homeowners, travel, mortgage  Small but attractive market:  4 million cars / $4 billion in addressable premiums  High internet penetration & propensity to shop  High premium levels & commission rates

26. Slide 26: Investments

    Investments 26

27. Slide 27: WTM Approach to Investments

    WTM Approach to Investments  Invest for total return  Policyholder funds invested conservatively:  Fixed income portfolio is short, safe and sound  Shareholder funds invested more aggressively:  Equity Exposure is 47% of Adjusted Shareholders’ Equity at 1Q14  Generally value-oriented  Include

28. Slide 28: Good Long-Term Track Record

    28 Good Long-Term Track Record 1Q14 1-year 5-year 13-year fixed income, ex currency 0.8% 0.6% 3.9% 4.6% equity, ex currency 2.7% 19.6% 9.9% 9.2% currency 0.0% -0.1% 0.4% 0.1% total portfolio 1.3% 5.2% 5.6% 5.5% benchmarks: Barclays Intermediate U.S. Aggregate barclays intermediate aggregate 1.2% -1.

29. Slide 29: Equity Exposure at Comfortable Levels

    [1] Defined as common shareholders' equity excluding equity in net urg(l) on Symetra's fixed maturity portfolio plus OneBeacon & HG Global non-controlling interests. 0% 10% 20% 30% 40% 50% 60% 70% 80% 90% 100% 2009 2010 2011 2012 2013 1Q14 Equity Exposure and Mix ($ in billions) Affiliated investmen

30. Slide 30: Fixed Income Playbook for 2014

    Fixed Income Playbook for 2014  We face an asymmetric market landscape:  Low rates  Tight spreads  More downside than upside  We are positioned for this market:  Short duration (2.0 – 2.5 years)  High credit quality (AA- weighted average)  Corporate debt focus (roughly 35% of the bond portfo

31. Slide 31: Capital

    Capital 31

32. Slide 32: Share Repurchases (2007-2013)

    Share Repurchases (2007-2013)  Repurchased 4.9 million shares (45% of the Company) for $2.2 billion at an average of $458 per share (71% of 2013 ABVPS) 32 Beginning Shares $ Average Shares O/S (000) millions per share millions 2007 291 145$ 499$ 10.8 2008 1,765 851 482 10.6 2009 - - - 8.8 2010 688

33. Slide 33: Consolidated Capitalization

    33 Consolidated Capitalization ($ in millions) 2012 2013 1Q14 Debt 751$ 676$ 678$ Non-controlling interest - SIG preference shares 250 250 250 Non-controlling interest - OneBeacon 251 274 279 Non-controlling interest - HG Global 17 17 18 Adjusted shareholders' equity 3,674 3,946 4,018 Total adjusted

34. Slide 34: What to Expect

    34 What to Expect  Growth in adjusted book value per share  Commitment to our operating principles:  Underwriting comes first  Maintain a disciplined balance sheet  Invest for total return  Think like owners  Capital management  Opportunistic approach to the business

35. Slide 35: Wise Words... Benjamin Graham

    35 Wise Words... Benjamin Graham “In the short run, the market is a voting machine, but in the long run it is a weighing machine.” Benjamin Graham

36. Slide 36: Q&A

    Q&A 36

37. Slide 37: Appendix

    Appendix 37

38. Slide 38: Non-GAAP Measure: WTM Adjusted Book Value per Share (ABVPS)

    Non-GAAP Measure: WTM Adjusted Book Value per Share (ABVPS) 38 White Mountains Insurance Group, Ltd. Reconciliation of GAAP book value per share to adjusted book value per share ($ in millions, except per share amounts; shares in thousands) Numerator 2012 2013 1Q14 GAAP common shareholders' equity (

39. Slide 39: Non-GAAP Measure: Sirius Group's Adjusted Book Value (ABV)

    Non-GAAP Measure: Sirius Group’s Adjusted Book Value (ABV) 39 White Mountains Insurance Group, Ltd. Reconciliation of Sirius Group's GAAP book value to adjusted book value ($ in millions) 2012 2013 1Q14 GAAP common shareholder's equity $ 1,713 $ 1,627 $ 1,721 equity in net unrealized (gains) losses

40. Slide 40: Non-GAAP Measure: Symetra's Operating ROE

    Non-GAAP Measure: Symetra’s Operating ROE 40 White Mountains Insurance Group, Ltd. Reconciliation of Symetra's GAAP ROE to operating ROE ($ in millions) 2013 GAAP net income $ 221 certain net realized gains (20) adjusted operating income $ 201 GAAP average common shareholders' equity $ 3,246 less: a

41. Slide 41: Non-GAAP Measure: Equity Exposure and Investments Adjusted Shareholders' Equity

    Non-GAAP Measure: Equity Exposure and Investments Adjusted Shareholders’ Equity 41 White Mountains Insurance Group, Ltd. Reconciliation of GAAP equity investments to equity exposure ($ in millions) 2009 2010 2011 2012 2013 1Q14 GAAP common, convertible and alternative investments $ 1,033 $ 1,246 $ 1

42. Slide 42: Non-GAAP Measure: 1Q14 Total Return, Fixed Income and Equity Total Return

    Non-GAAP Measure: 1Q14 Total Return, Fixed Income Total Return and Equity Total Return 42 White Mountains Insurance Group, Ltd. Reconciliation of GAAP investment returns to total return, fixed income total return and equity total return Investment Return Reconciliation - 1Q14 Total GAAP Adjusting To

43. Slide 43: Non-GAAP Measure: 2013 Total Return, Fixed Income and Equity Total Return

    Non-GAAP Measure: 2013 Total Return, Fixed Income Total Return and Equity Total Return 43 White Mountains Insurance Group, Ltd. Reconciliation of GAAP investment returns to total return, fixed income total return and equity total return Investment Return Reconciliation - 2013 Total GAAP Adjusting To

44. Slide 44: Non-GAAP Measure: 5-Year and 13-Year Periods Total Return

    Non-GAAP Measure: 5-Year and 13-Year Periods Total Return, Fixed Income Total Return and Equity Total Return 44 White Mountains Insurance Group, Ltd. Reconciliation of GAAP investment returns over 5-year and 13-year periods to total return, fixed income total return and equity total return GAAP Adju

45. Slide 45: Non-GAAP Measure: Adjusted Shareholders' Equity

    Non-GAAP Measure: Adjusted Shareholders’ Equity 45 White Mountains Insurance Group, Ltd. Reconciliation of GAAP common shareholders' equity to adjusted shareholders' equity ($ in millions) 2012 2013 1Q14 GAAP common shareholders' equity $ 3,732 $ 3,906 $ 4,015 equity in net unrealized (gains) losses

White Mountains Insurance Group — Investor Day (June 2014) on 6ix