What if you'd held WTM?
A $1,000 investment in White Mountains Insurance Group, Ltd. (WTM) at the month-end close of 1985-10 would be worth $90,953 at the close of 2026-08 — +8995.3% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $40,607.
Your scenario
Result
If you'd bought $1,000 at the start of each year
Value of $1,000 invested on January 1 of each year, held to 2026-08, dividends included.
Every year, $1,000 from 1985
| Year | Value of $1,000 | Year return |
|---|---|---|
| 1985 | $1,000 | — |
| 1986 | $1,145 | +14.5% |
| 1987 | $849 | -25.8% |
| 1988 | $981 | +15.6% |
| 1989 | $1,187 | +20.9% |
| 1990 | $1,804 | +52.0% |
| 1991 | $2,457 | +36.2% |
| 1992 | $2,531 | +3.0% |
| 1993 | $2,760 | +9.0% |
| 1994 | $2,540 | -8.0% |
| 1995 | $2,619 | +3.1% |
| 1996 | $3,381 | +29.1% |
| 1997 | $4,304 | +27.3% |
| 1998 | $5,042 | +17.1% |
| 1999 | $4,391 | -12.9% |
| 2000 | $11,730 | +167.1% |
| 2001 | $12,838 | +9.4% |
| 2002 | $11,952 | -6.9% |
| 2003 | $17,073 | +42.9% |
| 2004 | $24,028 | +40.7% |
| 2005 | $21,041 | -12.4% |
| 2006 | $22,158 | +5.3% |
| 2007 | $19,947 | -10.0% |
| 2008 | $10,457 | -47.6% |
| 2009 | $13,108 | +25.4% |
| 2010 | $13,261 | +1.2% |
| 2011 | $17,969 | +35.5% |
| 2012 | $20,449 | +13.8% |
| 2013 | $23,989 | +17.3% |
| 2014 | $25,107 | +4.7% |
| 2015 | $29,004 | +15.5% |
| 2016 | $33,405 | +15.2% |
| 2017 | $34,052 | +1.9% |
| 2018 | $34,350 | +0.9% |
| 2019 | $44,724 | +30.2% |
| 2020 | $40,168 | -10.2% |
| 2021 | $40,735 | +1.4% |
| 2022 | $56,876 | +39.6% |
| 2023 | $60,568 | +6.5% |
| 2024 | $78,321 | +29.3% |
| 2025 | $83,719 | +6.9% |
| 2026 | $85,820 | +2.5% |
Best and worst month-end to buy
The best single month-end close to have bought WTM was 1987-11 ($20.76): $1,000 then is $102,563 today. The worst was 2026-04 ($2,232): $1,000 then is $954.
FAQ
What would $1,000 in WTM be worth today?
A $1,000 investment in White Mountains Insurance Group, Ltd. (WTM) at the start of 1985 would be worth about $90,953 today, a total return of +8995.3%. Dividends are reinvested in these figures.
What were the best and worst years for WTM?
White Mountains Insurance Group, Ltd. (WTM)'s strongest calendar year since 1985 was 2000, a +167.1% return — $1,000 held through that year became about $2,671 by year-end. Its weakest year was 2008, at -47.6%.
Does the calculator include dividends and splits?
Yes where available. Prices are adjusted for both stock splits and reinvested dividends (total return), the same measure brokerages use.
How much would $100 per month in WTM have grown?
Investing $100 at the end of every month since 1985-10 would have grown to about $920,489 on $49,100 invested.
Did WTM beat the S&P 500?
Over the same period, $1,000 in the S&P 500 index would be worth $40,607. WTM beat the S&P 500 by +124.0% in total return.
Is this investment advice?
No. Wall Street Regrets is an entertainment and education tool. Every number is a historical calculation, not a prediction, and past performance never guarantees future results.
Methodology
White Mountains Insurance Group, Ltd. (WTM) historical total-return data from 1985-10 to 2026-08, reduced to month-end closes for the tables above.
Returns use adjusted close prices from Yahoo Finance historical data — adjusted for stock splits and reinvested dividends — the same convention used by major brokerages. A "year" scenario invests $1,000 at the prior December's month-end close and values it at the latest available month-end close. Non-USD amounts are converted at historical month-end exchange rates (Yahoo Finance): to USD on the buy date and back to your currency at the latest rate, so the return reflects the currency move as well as the asset.
Month-end resolution means intra-month extremes are not captured in tables; the calculator uses exact trading-day closes where daily data is available. Figures ignore taxes, fees, and the currency effects of non-USD listings. History is not a forecast. Wall Street Regrets is entertainment, not investment advice.
What if you'd held…
Data: adjusted close prices via Yahoo Finance. As of 2026-08. Not financial advice.