Wall Street RegretsThe regret calculator.

What if you'd held WINA?

A $1,000 investment in Winmark Corporation (WINA) at the month-end close of 1993-08 would be worth $33,997 at the close of 2026-08 — +3299.7% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $16,636.

$1,000 since 1993$33,997Total return+3299.7%Multiple34.0×CAGR+11.3%

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$33,997Gain+$32,997 (+3299.7%)Multiple34.0×CAGR+11.3%

    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$119,1702001$102,8202002$43,4602003$47,5672004$25,8832005$17,9582006$22,7722007$23,5672008$22,6652009$41,3802010$22,1442011$14,1172012$8,2582013$7,7072014$4,7302015$4,7392016$4,4172017$3,2442018$3,1522019$2,5552020$2,0382021$2,1272022$1,5342023$1,5782024$8642025$8932026$839

    Every year, $1,000 from 1993

    YearValue of $1,000Year return
    1993$1,000
    1994$599-40.1%
    1995$542-9.4%
    1996$493-9.1%
    1997$676+37.1%
    1998$732+8.4%
    1999$225-69.3%
    2000$261+15.9%
    2001$617+136.6%
    2002$564-8.6%
    2003$1,036+83.8%
    2004$1,493+44.1%
    2005$1,177-21.1%
    2006$1,138-3.4%
    2007$1,183+4.0%
    2008$648-45.2%
    2009$1,211+86.9%
    2010$1,899+56.9%
    2011$3,246+71.0%
    2012$3,479+7.1%
    2013$5,668+62.9%
    2014$5,657-0.2%
    2015$6,070+7.3%
    2016$8,265+36.2%
    2017$8,506+2.9%
    2018$10,494+23.4%
    2019$13,157+25.4%
    2020$12,605-4.2%
    2021$17,479+38.7%
    2022$16,992-2.8%
    2023$31,019+82.6%
    2024$30,010-3.3%
    2025$31,939+6.4%
    2026$26,808-16.1%

    Best and worst month-end to buy

    The best single month-end close to have bought WINA was 1999-09 ($2.17): $1,000 then is $155,415 today. The worst was 2025-09 ($481): $1,000 then is $701.

    FAQ

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

    A $1,000 investment in Winmark Corporation (WINA) at the start of 1993 would be worth about $33,997 today, a total return of +3299.7%. Dividends are reinvested in these figures.

    What were the best and worst years for WINA?

    Winmark Corporation (WINA)'s strongest calendar year since 1993 was 2001, a +136.6% return — $1,000 held through that year became about $2,366 by year-end. Its weakest year was 1999, at -69.3%.

    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 WINA have grown?

    Investing $100 at the end of every month since 1993-08 would have grown to about $933,859 on $39,700 invested.

    Did WINA beat the S&P 500?

    Over the same period, $1,000 in the S&P 500 index would be worth $16,636. WINA beat the S&P 500 by +104.4% 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

    Winmark Corporation (WINA) historical total-return data from 1993-08 to 2026-08, reduced to month-end closes for the tables above.

    Returns use adjusted close prices — adjusted for stock splits and reinvested dividends, the same convention used by major brokerages. End-of-day and live prices come from EODHD; parts of the deep historical series are carried over from Yahoo Finance data. 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 (EODHD): 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 EODHD and Yahoo Finance. As of 2026-08. Not financial advice.