Wall Street RegretsThe regret calculator.

What if you'd held RWT?

A $1,000 investment in Redwood Trust, Inc. (RWT) at the month-end close of 1995-08 would be worth $3,526 at the close of 2026-08 — +252.6% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $13,718.

$1,000 since 1995$3,526Total return+252.6%Multiple3.5×CAGR+4.1%

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$3,526Gain+$2,526 (+252.6%)Multiple3.5×CAGR+4.1%

    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.

    2000$4,8792001$3,0942002$2,0302003$1,6042004$7502005$5302006$7032007$4482008$6672009$1,3512010$1,3062011$1,1832012$1,6072013$8982014$7402015$6862016$9512017$7622018$7292019$6662020$5642021$9842022$6152023$1,0642024$8752025$8992026$937

    Every year, $1,000 from 1995

    YearValue of $1,000Year return
    1995$1,000
    1996$2,127+112.7%
    1997$1,240-41.7%
    1998$869-30.0%
    1999$802-7.7%
    2000$1,264+57.7%
    2001$1,926+52.4%
    2002$2,439+26.6%
    2003$5,217+113.9%
    2004$7,375+41.4%
    2005$5,560-24.6%
    2006$8,730+57.0%
    2007$5,866-32.8%
    2008$2,895-50.6%
    2009$2,994+3.4%
    2010$3,305+10.4%
    2011$2,434-26.4%
    2012$4,355+78.9%
    2013$5,287+21.4%
    2014$5,697+7.7%
    2015$4,111-27.8%
    2016$5,134+24.9%
    2017$5,365+4.5%
    2018$5,870+9.4%
    2019$6,935+18.2%
    2020$3,974-42.7%
    2021$6,364+60.1%
    2022$3,674-42.3%
    2023$4,468+21.6%
    2024$4,352-2.6%
    2025$4,174-4.1%
    2026$3,911-6.3%

    Best and worst month-end to buy

    The best single month-end close to have bought RWT was 1999-11 ($0.90): $1,000 then is $5,355 today. The worst was 2007-01 ($11.80): $1,000 then is $409.

    FAQ

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

    A $1,000 investment in Redwood Trust, Inc. (RWT) at the start of 1995 would be worth about $3,526 today, a total return of +252.6%. Dividends are reinvested in these figures.

    What were the best and worst years for RWT?

    Redwood Trust, Inc. (RWT)'s strongest calendar year since 1995 was 2003, a +113.9% return — $1,000 held through that year became about $2,139 by year-end. Its weakest year was 2008, at -50.6%.

    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 RWT have grown?

    Investing $100 at the end of every month since 1995-08 would have grown to about $51,958 on $37,300 invested.

    Did RWT beat the S&P 500?

    Over the same period, $1,000 in the S&P 500 index would be worth $13,718. RWT trailed the S&P 500 by +74.3% 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

    Redwood Trust, Inc. (RWT) historical total-return data from 1995-08 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.