Wall Street RegretsThe regret calculator.

What if you'd held WTFC?

A $1,000 investment in Wintrust Financial Corporation (WTFC) at the month-end close of 1998-04 would be worth $15,512 at the close of 2026-08 — +1451.2% total return, dividends reinvested. The same $1,000 in the S&P 500, dividends reinvested, would be worth $11,517.

$1,000 since 1998$15,512Total return+1451.2%Multiple15.5×CAGR+10.2%

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$15,512Gain+$14,512 (+1451.2%)Multiple15.5×CAGR+10.2%

    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$19,7102001$18,7672002$9,7302003$6,2992004$4,3532005$3,4322006$3,5452007$4,0312008$5,8002009$9,2142010$6,0622011$5,6192012$6,5782013$5,0022014$3,9612015$3,8722016$3,6992017$2,4492018$2,1412019$2,6292020$2,4312021$2,7552022$1,8232023$1,9302024$1,7242025$1,2602026$1,106

    Every year, $1,000 from 1998

    YearValue of $1,000Year return
    1998$1,000
    1999$777-22.3%
    2000$816+5.0%
    2001$1,574+92.9%
    2002$2,430+54.5%
    2003$3,518+44.7%
    2004$4,460+26.8%
    2005$4,318-3.2%
    2006$3,798-12.1%
    2007$2,640-30.5%
    2008$1,662-37.0%
    2009$2,526+52.0%
    2010$2,725+7.9%
    2011$2,327-14.6%
    2012$3,061+31.5%
    2013$3,865+26.3%
    2014$3,954+2.3%
    2015$4,139+4.7%
    2016$6,252+51.1%
    2017$7,150+14.4%
    2018$5,823-18.6%
    2019$6,298+8.2%
    2020$5,557-11.8%
    2021$8,396+51.1%
    2022$7,931-5.5%
    2023$8,883+12.0%
    2024$12,154+36.8%
    2025$13,848+13.9%
    2026$15,310+10.6%

    Best and worst month-end to buy

    The best single month-end close to have bought WTFC was 2000-03 ($7.27): $1,000 then is $21,039 today. The worst was 2026-06 ($160): $1,000 then is $955.

    FAQ

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

    A $1,000 investment in Wintrust Financial Corporation (WTFC) at the start of 1998 would be worth about $15,512 today, a total return of +1451.2%. Dividends are reinvested in these figures.

    What were the best and worst years for WTFC?

    Wintrust Financial Corporation (WTFC)'s strongest calendar year since 1998 was 2001, a +92.9% return — $1,000 held through that year became about $1,929 by year-end. Its weakest year was 2008, at -37.0%.

    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 WTFC have grown?

    Investing $100 at the end of every month since 1998-04 would have grown to about $190,623 on $34,100 invested.

    Did WTFC beat the S&P 500?

    Over the same period, $1,000 in the S&P 500 with dividends reinvested (the S&P 500 Total Return index) would be worth $11,517. WTFC beat the S&P 500 by +34.7% 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

    Wintrust Financial Corporation (WTFC) historical total-return data from 1998-04 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.