Tax Managed Investing: Deciding When to Realize Capital Gains

For taxable investors with sizable gains in their brokerage accounts, the decision when to realize that capital gain is intensely personal—depending of course on individual circumstances, while also factoring in market return expectations and the prevailing tax structure.

Let’s look at the context for capital gain realization in 2025, informed by historical experience and potential future paths of tax policy.

Could 2025 be another year of strong market returns?

After two consecutive years of 20%-plus market returns—the first time that’s happened since the late 1990’s dot-com bubble—many investors face the prospect of capital gains. Even if we look further back to include the 2022 loss of 18.11% in the S&P 500® Index, the annualized five-year average return of 14.53% has been historically robust.

We can point to fundamental reasons why the stock market may be unable to sustain such a torrid pace—and could even take a step back, given the volatility we’ve witnessed so far in the first quarter. Yet many market watchers are still decidedly bullish on 2025. Early this year, analysts at several prominent banks called for the S&P 500® to end the year at 7000. If their predictions turn out to be accurate, the appreciation would represent another 15% gain.

What do historical patterns of capital gain realization tell us?

When making choices whether to realize gains, investors might be just as concerned about the taxes they would have to pay on those gains. Considering the historical data may be quite instructive, and for that we turn to the Congressional Budget Office (CBO), which has been assiduously keeping track of such statistics for many decades. The CBO even makes projections of the likely tax collections from various income sources, which serves as an input into budgetary decisions on government spending and therefore tax policy.

Display 1 shows that over the last 50 years or so, the dollar value of capital gain realization has risen along with the stock market’s appreciation, while also experiencing ebbs and flows. A record $2.07 trillion dollars in capital gains was realized in 2021, representing an 80.5% jump from 2020, which was then followed by a 40% reduction in realization in 2022.

What accounts for this dynamic? The S&P 500’s 28.7% appreciation in 2021 is clearly one factor. But more broadly, from the pandemic bottom in March 2020 through year end 2024, the S&P 500 has gone up by approximately 183%. That drove investors to realize much of their gains. Once realized, fewer gains remained for the following year, and another build up cycle began.

Over the past decade, in the years running up to the 2020–2022 realization pattern, average household income from capital gains has also been on the rise. Display 2 highlights that the average income from realized capital gains reached an all-time high of $15,700 in 2021—about 60% higher than its previous peak in 2007. According to CBO estimates, 32 million households realized capital gains in 2021. Among those households, the average income from capital gains was $64,200. In 2020, by comparison, 28 million households realized capital gains, averaging $40,200 per household.

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