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White Mountains Insurance Group (WTM)
NYSE:WTM
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White Mountains Insurance Group (WTM) AI Stock Analysis

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WTM

White Mountains Insurance Group

(NYSE:WTM)

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Neutral 68 (OpenAI - 5.2)
Rating:68Neutral
Price Target:
$2,303.00
▲(13.50% Upside)
Action:Reiterated
Date:05/15/26
The score is driven primarily by strong recent profitability/ROE and conservative leverage, partially offset by volatility in revenue and cash flow conversion. Technical indicators point to weak near-term momentum, valuation is harder to assess due to a negative P/E despite a solid dividend yield, and recent corporate actions are modestly supportive.
Positive Factors
Strong recent profitability and ROE
White Mountains has generated materially higher net income and margins in the latest period, producing a sustained ROE (~20% in 2025/TTM). Persistent elevated profitability supports capital generation and reinvestment capacity, underpinning long-term franchise value.
Negative Factors
Variable cash conversion
Earnings-to-cash timing swings create unpredictability in distributable cash and capital planning. Negative operating cash flow in a recent year reduces near-term optionality for buybacks/dividends and raises reliance on investment or financing to fund capital actions.
Read all positive and negative factors
Positive Factors
Negative Factors
Strong recent profitability and ROE
White Mountains has generated materially higher net income and margins in the latest period, producing a sustained ROE (~20% in 2025/TTM). Persistent elevated profitability supports capital generation and reinvestment capacity, underpinning long-term franchise value.
Read all positive factors

White Mountains Insurance Group (WTM) vs. SPDR S&P 500 ETF (SPY)

White Mountains Insurance Group Business Overview & Revenue Model

Company Description
White Mountains Insurance Group, Ltd., through its subsidiaries, provides insurance and other financial services in the United States. The company operates through five segments: HG Global/BAM, Ark, NSM, Kudu, and Other Operations. The HG Global/B...
How the Company Makes Money
WTM’s earnings are primarily generated through (1) underwriting income and fee income earned by its insurance and insurance-services subsidiaries and (2) investment income and realized/unrealized gains on the investment portfolios and equity stake...

White Mountains Insurance Group Financial Statement Overview

Summary
Strong recent profitability and ROE with generally conservative leverage, but fundamentals are less predictable due to volatile/negative TTM revenue growth, balance-sheet swings, and uneven cash conversion (including negative operating/free cash flow in 2025 despite strong net income).
Income Statement
82
Very Positive
Balance Sheet
78
Positive
Cash Flow
62
Positive
BreakdownTTMDec 2025Dec 2024Dec 2023Dec 2022Dec 2021
Income Statement
Total Revenue2.64B2.71B2.35B2.17B1.16B614.40M
Gross Profit1.56B1.45B1.07B1.15B370.90M33.10M
EBITDA1.32B1.41B371.10M610.30M-104.80M-231.50M
Net Income1.04B1.11B230.40M509.20M792.80M-275.40M
Balance Sheet
Total Assets7.13B12.31B9.93B8.39B7.39B7.00B
Cash, Cash Equivalents and Short-Term Investments97.30M3.15B1.22B1.61B1.18B605.80M
Total Debt834.80M837.00M562.50M564.60M575.20M639.10M
Total Liabilities5.59B6.05B4.79B3.82B3.45B3.30B
Stockholders Equity5.37B5.43B4.48B4.24B3.75B3.55B
Cash Flow
Free Cash Flow635.00M-7.20M586.80M404.10M434.00M98.20M
Operating Cash Flow635.00M-7.20M586.80M404.10M434.00M98.20M
Investing Cash Flow-782.30M212.70M-447.00M-543.90M155.70M-204.00M
Financing Cash Flow-27.70M-205.20M4.20M7.20M-461.80M149.20M

White Mountains Insurance Group Technical Analysis

Technical Analysis Sentiment
Positive
Last Price2029.06
Price Trends
50DMA
2203.53
Negative
100DMA
2161.71
Negative
200DMA
2020.85
Positive
Market Momentum
MACD
-26.31
Negative
RSI
44.40
Neutral
STOCH
60.86
Neutral
Evaluating momentum and price trends is crucial in stock analysis to make informed investment decisions. For WTM, the sentiment is Positive. The current price of 2029.06 is below the 20-day moving average (MA) of 2166.84, below the 50-day MA of 2203.53, and above the 200-day MA of 2020.85, indicating a neutral trend. The MACD of -26.31 indicates Negative momentum. The RSI at 44.40 is Neutral, neither overbought nor oversold. The STOCH value of 60.86 is Neutral, not indicating any strong overbought or oversold conditions. Overall, these indicators collectively point to a Positive sentiment for WTM.

White Mountains Insurance Group Risk Analysis

White Mountains Insurance Group disclosed 19 risk factors in its most recent earnings report. White Mountains Insurance Group reported the most risks in the "Legal & Regulatory" category.
Finance & Corporate - Financial and accounting risks. Risks related to the execution of corporate activity and strategy
Latest Risks Added 0 New Risks

White Mountains Insurance Group Peers Comparison

Overall Rating
UnderperformOutperform
Sector (68)
Financial Indicators
Name
Overall Rating
Market Cap
P/E Ratio
ROE
Dividend Yield
Revenue Growth
EPS Growth
80
Outperform
$5.34B11.6712.93%1.85%8.76%99.32%
78
Outperform
$5.70B6.4136.48%1.34%9.70%193.37%
68
Neutral
$5.31B-45.1120.61%0.05%30.09%3444.41%
68
Neutral
$18.00B11.429.92%3.81%9.73%1.22%
61
Neutral
$3.79B-59.2214.47%13.84%27.24%
55
Neutral
$1.74B-264.261.52%3.15%0.51%-88.36%
52
Neutral
$4.41B-33.40-26.52%57.13%38.73%
* Financial Sector Average
Performance Comparison
Ticker
Company Name
Price
Change
% Change
WTM
White Mountains Insurance Group
2,144.81
310.64
16.94%
MCY
Mercury General
102.93
43.37
72.81%
SIGI
Selective Insurance Group
89.22
3.74
4.37%
KMPR
Kemper
29.50
-30.82
-51.10%
LMND
Lemonade
57.36
28.27
97.18%
HGTY
Hagerty Inc Class A
11.05
1.80
19.46%

White Mountains Insurance Group Corporate Events

Business Operations and StrategyPrivate Placements and Financing
White Mountains Issues New Notes, Refinances Debt, Returns Capital
Positive
May 15, 2026
On May 15, 2026, White Mountains Insurance Group said its subsidiary HG Global Ltd. completed a $200 million private placement of fixed rate senior secured notes under a May 14, 2026 note purchase agreement. The new 10-year notes, bearing a 7.39% ...
Business Operations and StrategyM&A TransactionsPrivate Placements and Financing
White Mountains Partners Acquires Majority Stake in BaseSix
Positive
Apr 1, 2026
On April 1, 2026, White Mountains Partners, an operating company of White Mountains Insurance Group, acquired a majority interest in BaseSix Systems LLC, a Marietta, Georgia-based provider of building systems integration and aftermarket services f...
Business Operations and StrategyFinancial DisclosuresPrivate Placements and Financing
White Mountains Invests in Bishop Street MGA Platform
Positive
Feb 27, 2026
On February 26, 2026, Bishop Street Underwriters, a RedBird Capital Partners portfolio company and diversified platform of managing general agents and niche underwriting teams in the property and casualty sector, closed a $125 million structured c...
Glossary
BuyA stock rated as a "Buy" is expected to perform better than the overall market or a specific benchmark over the near-to-medium term. This rating suggests the stock is likely to deliver higher returns compared to other stocks in the same sector or market index. Note: This is not investment advice; please consult a financial advisor before making investment decisions.
HoldA stock rated as a "Hold" is expected to perform in line with the overall market or a specific benchmark. This rating indicates that the stock is neither particularly compelling nor unfavorable for investment. Note: This is not investment advice; please consult a financial advisor before making investment decisions.
SellA stock rated as a "Sell" is expected to perform worse than the overall market or a specific benchmark over the near-to-medium term. This rating suggests the stock may deliver lower returns compared to other stocks in the same sector or market index. Note: This is not investment advice; please consult a financial advisor before making investment decisions.

Disclaimer

This AI Analyst Stock Report is automatically generated by our AI systems using advanced algorithms and publicly available financial, technical, and market data. While the information provided aims to be accurate and insightful, it is intended for informational purposes only and should not be considered financial advice. Any content created by an AI (Artificial Intelligence) system may contain inaccuracies and/or contain errors. Investing in stocks carries inherent risks, and past performance is not indicative of future results. This report does not account for your personal financial circumstances, objectives, or risk tolerance. Always conduct your own research or consult with a qualified financial advisor before making investment decisions. The analysis and recommendations provided are based on historical and current data and may not fully reflect future market conditions or unexpected developments. Neither the creators of this report nor its affiliated entities guarantee the accuracy, completeness, or reliability of the information presented. Use this report at your own discretion and risk.Date of analysis: May 15, 2026