Wall Street RegretsThe regret calculator.

What if you'd held SSPY?

A $1,000 investment in Stratified LargeCap Index ETF (SSPY) at the month-end close of 2014-12 would be worth $3,511 at the close of 2026-08 — +251.1% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $3,744.

$1,000 since 2014$3,511Total return+251.1%Multiple3.5×CAGR+11.4%

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$3,511Gain+$2,511 (+251.1%)Multiple3.5×CAGR+11.4%

    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.

    2014$3,5112015$3,5112016$3,5632017$3,1222018$2,6082019$2,7902020$2,1652021$1,9302022$1,4982023$1,6492024$1,4512025$1,3182026$1,168

    Every year, $1,000 from 2014

    YearValue of $1,000Year return
    2014$1,000
    2015$985-1.5%
    2016$1,125+14.1%
    2017$1,346+19.7%
    2018$1,258-6.6%
    2019$1,621+28.9%
    2020$1,819+12.2%
    2021$2,344+28.8%
    2022$2,128-9.2%
    2023$2,420+13.7%
    2024$2,664+10.1%
    2025$3,007+12.9%
    2026$3,511+16.8%

    Best and worst month-end to buy

    The best single month-end close to have bought SSPY was 2016-01 ($26.95): $1,000 then is $3,765 today. The worst was 2026-08 ($101): $1,000 then is $1,000.

    FAQ

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

    A $1,000 investment in Stratified LargeCap Index ETF (SSPY) at the start of 2014 would be worth about $3,511 today, a total return of +251.1%. Dividends are reinvested in these figures.

    What were the best and worst years for SSPY?

    Stratified LargeCap Index ETF (SSPY)'s strongest calendar year since 2014 was 2019, a +28.9% return — $1,000 held through that year became about $1,289 by year-end. Its weakest year was 2022, at -9.2%.

    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 SSPY have grown?

    Investing $100 at the end of every month since 2014-12 would have grown to about $30,533 on $14,100 invested.

    Did SSPY beat the S&P 500?

    Over the same period, $1,000 in the S&P 500 index would be worth $3,744. SSPY trailed the S&P 500 by +6.2% 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

    Stratified LargeCap Index ETF (SSPY) historical total-return data from 2014-12 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.