What if you'd held SSO?
A $1,000 investment in ProShares Ultra S&P500 (SSO) at the month-end close of 2006-06 would be worth $18,918 at the close of 2026-08 — +1791.8% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $6,068.
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 2006
| Year | Value of $1,000 | Year return |
|---|---|---|
| 2006 | $1,000 | — |
| 2007 | $1,011 | +1.1% |
| 2008 | $324 | -67.9% |
| 2009 | $477 | +47.2% |
| 2010 | $605 | +26.8% |
| 2011 | $587 | -2.9% |
| 2012 | $769 | +31.0% |
| 2013 | $1,312 | +70.5% |
| 2014 | $1,647 | +25.5% |
| 2015 | $1,627 | -1.2% |
| 2016 | $1,973 | +21.3% |
| 2017 | $2,848 | +44.4% |
| 2018 | $2,432 | -14.6% |
| 2019 | $3,975 | +63.4% |
| 2020 | $4,832 | +21.5% |
| 2021 | $7,758 | +60.6% |
| 2022 | $4,734 | -39.0% |
| 2023 | $6,942 | +46.7% |
| 2024 | $9,961 | +43.5% |
| 2025 | $12,569 | +26.2% |
| 2026 | $15,430 | +22.8% |
Best and worst month-end to buy
The best single month-end close to have bought SSO was 2009-02 ($0.98): $1,000 then is $72,255 today. The worst was 2026-08 ($70.81): $1,000 then is $1,000.
FAQ
What would $1,000 in SSO be worth today?
A $1,000 investment in ProShares Ultra S&P500 (SSO) at the start of 2006 would be worth about $18,918 today, a total return of +1791.8%. Dividends are reinvested in these figures.
What were the best and worst years for SSO?
ProShares Ultra S&P500 (SSO)'s strongest calendar year since 2006 was 2013, a +70.5% return — $1,000 held through that year became about $1,705 by year-end. Its weakest year was 2008, at -67.9%.
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 SSO have grown?
Investing $100 at the end of every month since 2006-06 would have grown to about $303,046 on $24,300 invested.
Did SSO beat the S&P 500?
Over the same period, $1,000 in the S&P 500 index would be worth $6,068. SSO beat the S&P 500 by +211.7% 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
ProShares Ultra S&P500 (SSO) historical total-return data from 2006-06 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.