Wall Street RegretsThe regret calculator.

What if you'd held TBT?

A $1,000 investment in ProShares UltraShort Lehman 20 Year Treasury (TBT) at the month-end close of 2008-05 would be worth $155 at the close of 2026-08 — -84.5% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $5,504.

$1,000 since 2008$155Total return-84.5%Multiple0.16×CAGR-9.7%

Your scenario

Dates resolve to the nearest month-end close.
Leave empty for "held until today".
Invested at each month-end. Starts on the buy date.

Result

Worth$155Gain+$-845 (-84.5%)Multiple0.2×CAGR-9.7%

    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.

    2008$1552009$2982010$2262011$3042012$6232013$7092014$5682015$9702016$1,0212017$1,1032018$1,3322019$1,2692020$1,6462021$2,6532022$2,5782023$1,3342024$1,3672025$1,0712026$1,086

    Every year, $1,000 from 2008

    YearValue of $1,000Year return
    2008$1,000
    2009$1,322+32.2%
    2010$982-25.7%
    2011$479-51.2%
    2012$420-12.2%
    2013$525+24.8%
    2014$307-41.4%
    2015$292-5.0%
    2016$270-7.4%
    2017$224-17.2%
    2018$235+5.0%
    2019$181-22.9%
    2020$112-37.9%
    2021$116+2.9%
    2022$224+93.3%
    2023$218-2.5%
    2024$278+27.7%
    2025$274-1.4%
    2026$298+8.6%

    Best and worst month-end to buy

    The best single month-end close to have bought TBT was 2020-07 ($12.53): $1,000 then is $2,998 today. The worst was 2008-05 ($242): $1,000 then is $155.

    FAQ

    What would $1,000 in TBT be worth today?

    A $1,000 investment in ProShares UltraShort Lehman 20 Year Treasury (TBT) at the start of 2008 would be worth about $155 today, a total return of -84.5%. Dividends are reinvested in these figures.

    What were the best and worst years for TBT?

    ProShares UltraShort Lehman 20 Year Treasury (TBT)'s strongest calendar year since 2008 was 2022, a +93.3% return — $1,000 held through that year became about $1,933 by year-end. Its weakest year was 2011, at -51.2%.

    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 TBT have grown?

    Investing $100 at the end of every month since 2008-05 would have grown to about $24,654 on $22,000 invested.

    Did TBT beat the S&P 500?

    Over the same period, $1,000 in the S&P 500 index would be worth $5,504. TBT trailed the S&P 500 by +97.2% 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 UltraShort Lehman 20 Year Treasury (TBT) historical total-return data from 2008-05 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.

    Full methodology →

    What if you'd held…

    Data: adjusted close prices via Yahoo Finance. As of 2026-08. Not financial advice.