Wall Street RegretsThe regret calculator.

What if you'd held PENN?

A $1,000 investment in PENN Entertainment, Inc. (PENN) at the month-end close of 1994-05 would be worth $95,179 at the close of 2026-08 — +9417.9% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $16,885.

$1,000 since 1994$95,179Total return+9417.9%Multiple95.2×CAGR+15.2%

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$95,179Gain+$94,179 (+9417.9%)Multiple95.2×CAGR+15.2%

    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$36,4642001$32,2222002$10,8222003$10,3512004$7,1002005$2,7112006$2,4912007$1,9722008$1,3782009$3,8392010$3,0192011$2,3352012$2,1562013$1,6722014$1,2952015$1,3522016$1,1592017$1,3462018$5922019$9862020$7262021$2152022$3582023$6252024$7132025$9362026$1,258

    Every year, $1,000 from 1994

    YearValue of $1,000Year return
    1994$1,000
    1995$1,992+99.2%
    1996$6,598+231.3%
    1997$4,516-31.6%
    1998$3,246-28.1%
    1999$4,172+28.5%
    2000$4,721+13.2%
    2001$14,057+197.7%
    2002$14,697+4.5%
    2003$21,426+45.8%
    2004$56,107+161.9%
    2005$61,066+8.8%
    2006$77,131+26.3%
    2007$110,361+43.1%
    2008$39,623-64.1%
    2009$50,385+27.2%
    2010$65,139+29.3%
    2011$70,549+8.3%
    2012$91,008+29.0%
    2013$117,459+29.1%
    2014$112,541-4.2%
    2015$131,311+16.7%
    2016$113,033-13.9%
    2017$256,803+127.2%
    2018$154,344-39.9%
    2019$209,508+35.7%
    2020$707,951+237.9%
    2021$425,000-40.0%
    2022$243,443-42.7%
    2023$213,279-12.4%
    2024$162,459-23.8%
    2025$120,902-25.6%
    2026$152,131+25.8%

    Best and worst month-end to buy

    The best single month-end close to have bought PENN was 1994-12 ($0.12): $1,000 then is $152,131 today. The worst was 2021-02 ($116): $1,000 then is $160.

    FAQ

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

    A $1,000 investment in PENN Entertainment, Inc. (PENN) at the start of 1994 would be worth about $95,179 today, a total return of +9417.9%. Dividends are reinvested in these figures.

    What were the best and worst years for PENN?

    PENN Entertainment, Inc. (PENN)'s strongest calendar year since 1994 was 2020, a +237.9% return — $1,000 held through that year became about $3,379 by year-end. Its weakest year was 2008, at -64.1%.

    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 PENN have grown?

    Investing $100 at the end of every month since 1994-05 would have grown to about $484,259 on $38,800 invested.

    Did PENN beat the S&P 500?

    Over the same period, $1,000 in the S&P 500 index would be worth $16,885. PENN beat the S&P 500 by +463.7% 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

    PENN Entertainment, Inc. (PENN) historical total-return data from 1994-05 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.