What if you'd held KWY?
A $1,000 investment in Kingsway Corporation (KWY) at the month-end close of 2001-07 would be worth $309 at the close of 2026-09 — -69.1% total return, dividends reinvested. The same $1,000 in the S&P 500, dividends reinvested, would be worth $10,228.
Your scenario
Result
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 2026-09, dividends included.
Every year, $1,000 from 2001
| Year | Value of $1,000 | Year return |
|---|---|---|
| 2001 | $1,000 | — |
| 2002 | $690 | -31.0% |
| 2003 | $905 | +31.1% |
| 2004 | $1,267 | +40.0% |
| 2005 | $1,624 | +28.1% |
| 2006 | $1,701 | +4.8% |
| 2007 | $996 | -41.5% |
| 2008 | $469 | -52.9% |
| 2009 | $153 | -67.4% |
| 2010 | $124 | -18.9% |
| 2011 | $45.47 | -63.4% |
| 2012 | $83.30 | +83.2% |
| 2013 | $85.26 | +2.4% |
| 2014 | $121 | +42.3% |
| 2015 | $99.91 | -17.7% |
| 2016 | $137 | +36.8% |
| 2017 | $110 | -19.2% |
| 2018 | $62.75 | -43.2% |
| 2019 | $40.66 | -35.2% |
| 2020 | $103 | +152.7% |
| 2021 | $120 | +16.6% |
| 2022 | $173 | +44.7% |
| 2023 | $184 | +5.9% |
| 2024 | $183 | -0.4% |
| 2025 | $294 | +60.7% |
| 2026 | $220 | -25.1% |
Best and worst month-end to buy
The best single month-end close to have bought KWY was 2020-01 ($1.70): $1,000 then is $5,929 today. The worst was 2006-10 ($85.57): $1,000 then is $118.
FAQ
What would $1,000 in KWY be worth today?
A $1,000 investment in Kingsway Corporation (KWY) at the start of 2001 would be worth about $309 today, a total return of -69.1%. Dividends are reinvested in these figures.
What were the best and worst years for KWY?
Kingsway Corporation (KWY)'s strongest calendar year since 2001 was 2020, a +152.7% return — $1,000 held through that year became about $2,527 by year-end. Its weakest year was 2009, at -67.4%.
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 KWY have grown?
Investing $100 at the end of every month since 2001-07 would have grown to about $48,717 on $30,300 invested.
Did KWY 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 $10,228. KWY trailed the S&P 500 by +97.0% 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
Kingsway Corporation (KWY) historical total-return data from 2001-07 to 2026-09, 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.
What if you'd held…
Data: adjusted close prices via EODHD and Yahoo Finance. As of 2026-09-03. Not financial advice.