Wall Street RegretsThe regret calculator.

What if you'd held HIO?

A $1,000 investment in Western Asset High Income Opportunity Fund, Inc. (HIO) at the month-end close of 1993-11 would be worth $5,669 at the close of 2026-08 — +466.9% total return, dividends reinvested. The same $1,000 in the S&P 500 would be worth $16,692.

$1,000 since 1993$5,669Total return+466.9%Multiple5.7×CAGR+5.4%

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$5,669Gain+$4,669 (+466.9%)Multiple5.7×CAGR+5.4%

    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.

    2000$4,7982001$4,2082002$4,3632003$4,6292004$3,6852005$3,6032006$3,7082007$3,0582008$3,1642009$4,2432010$2,4902011$2,2252012$2,0122013$1,7822014$1,7942015$1,8392016$1,9332017$1,6612018$1,5232019$1,6472020$1,3252021$1,2482022$1,1062023$1,3342024$1,2342025$1,0842026$1,028

    Every year, $1,000 from 1993

    YearValue of $1,000Year return
    1993$1,000
    1994$857-14.3%
    1995$981+14.5%
    1996$1,188+21.1%
    1997$1,426+20.1%
    1998$1,305-8.5%
    1999$1,180-9.6%
    2000$1,345+14.0%
    2001$1,297-3.5%
    2002$1,223-5.8%
    2003$1,536+25.6%
    2004$1,571+2.3%
    2005$1,526-2.8%
    2006$1,851+21.2%
    2007$1,789-3.4%
    2008$1,334-25.4%
    2009$2,273+70.4%
    2010$2,544+11.9%
    2011$2,812+10.6%
    2012$3,176+12.9%
    2013$3,154-0.7%
    2014$3,078-2.4%
    2015$2,928-4.9%
    2016$3,407+16.3%
    2017$3,715+9.1%
    2018$3,437-7.5%
    2019$4,272+24.3%
    2020$4,536+6.2%
    2021$5,118+12.8%
    2022$4,243-17.1%
    2023$4,588+8.1%
    2024$5,219+13.8%
    2025$5,506+5.5%
    2026$5,660+2.8%

    Best and worst month-end to buy

    The best single month-end close to have bought HIO was 1994-12 ($0.54): $1,000 then is $6,605 today. The worst was 2026-06 ($3.60): $1,000 then is $988.

    FAQ

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

    A $1,000 investment in Western Asset High Income Opportunity Fund, Inc. (HIO) at the start of 1993 would be worth about $5,669 today, a total return of +466.9%. Dividends are reinvested in these figures.

    What were the best and worst years for HIO?

    Western Asset High Income Opportunity Fund, Inc. (HIO)'s strongest calendar year since 1993 was 2009, a +70.4% return — $1,000 held through that year became about $1,704 by year-end. Its weakest year was 2008, at -25.4%.

    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 HIO have grown?

    Investing $100 at the end of every month since 1993-11 would have grown to about $113,070 on $39,400 invested.

    Did HIO beat the S&P 500?

    Over the same period, $1,000 in the S&P 500 index would be worth $16,692. HIO trailed the S&P 500 by +66.0% 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

    Western Asset High Income Opportunity Fund, Inc. (HIO) historical total-return data from 1993-11 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.