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President Donald Trump says he knows what would have fixed Social Security’s money problem, and he says he wanted it from the start: put the trust fund in stocks.
“I wanted to ride with Social Security being fully invested in the stock market,” Trump said Oct. 7 at a White House event announcing automatic enrollment of children in Trump Accounts.
“Had we done that, Social Security would right now be the richest entity anywhere in the world.” Had it happened, he added, “People wouldn’t be talking about Social Security difficulty.” (1)
I’ve been a CPA since 1981, and I was a stockbroker on Black Monday in 1987.
Here’s what’s true: stocks have crushed safe government bonds since 2017. Here’s what isn’t: that stocks would have made Social Security’s problems go away.
The program’s Old-Age and Survivors Insurance (retirement) trust fund is still projected to run dry in the fourth quarter of 2032, when only 78% of scheduled benefits could be paid. (2) Today, every security in the trust funds is a “special issue” of the U.S. Treasury. (3)
Here are five things retirees should know about Trump’s idea, and what it means for your own check.
1. He’s right that stocks beat Treasurys, by a lot
According to historical return data compiled by NYU Stern professor Aswath Damodaran, the S&P 500, with dividends, returned about 252% from the start of 2017 through the end of 2025. In other words, $1 grew to roughly $3.52. The same dollar in 10-year Treasury bonds grew to about $1.09. (4)
At the end of 2016, Social Security’s combined trust funds held about $2.85 trillion. (5)
My rough math: had all of it gone into the S&P 500 and simply sat there, it would have been worth roughly $10 trillion by the end of 2025. Using the 10-year Treasury yardstick instead, it would have been about $3.1 trillion.
So yes, on paper, the stock route comes out roughly $7 trillion ahead. That’s the part of Trump’s pitch that holds up.
2. Even $7 trillion wouldn’t fix the problem
Social Security’s trustees put the program’s shortfall through 2100 at $29.3 trillion in today’s dollars. (6) Put another way, the long-range gap equals 4.42% of all taxable payroll. (2)
That means my best-case, never-touched gain covers roughly a quarter of the hole.
“The richest entity anywhere in the world”? Maybe. It still wouldn’t be enough. And his claim that people “wouldn’t be talking about Social Security difficulty” isn’t what the numbers say.
3. Social Security is a seller, not a saver
Here’s the part the stock pitch skips. Social Security’s total cost has exceeded its total income every year since 2021, according to the trustees. (7) The trust funds are shrinking. Combined reserves fell by $160 billion in 2025 alone, to $2.56 trillion. (2)
A fund that pays out more than it takes in has to sell something every year. Now picture it selling stocks in 2022, when the S&P 500 lost 18.04%. Or in 2008, when it lost 36.55%. (4)
My hypothetical in No. 1 never sold a share. The real program would have.
Anyone who sat at a brokerage desk in 1987, as I did, knows who gets hurt worst in a crash: the investor who’s forced to sell when prices are down. A program that has to mail checks every month is a forced seller.
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4. You can do what Trump wanted, with your own money
Your Social Security check is the steady part of your retirement. Since 1975, its general increases have been tied to the cost of living. (8) The 2026 adjustment was 2.8%. (8)
That steadiness is exactly why you don’t need Social Security to gamble.
If your check covers a big share of your basic bills, then in my view the money in your own IRA or 401(k) can afford to carry more stock risk than you might think, as long as you won’t need to sell it in a bad year.
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5. Plan for 2032 as if the cut could happen
Congress can still fix this. Nobody knows how or when. If lawmakers do nothing, the trustees project that 78% of scheduled benefits would be payable once the retirement fund runs dry. (2)
For a $2,000 monthly check, a 22% cut is $440 a month.
That doesn’t mean you should panic. It means your plan should still work if that happens. Run your budget at 78% of your expected benefit and see what breaks. Then decide now what you’d trim, sell or tap, rather than deciding under pressure later.
This is where a second set of eyes pays off. A service like SmartAsset can match you with up to three fiduciary advisors, who are legally required to put your interests first.
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My take
Trump’s instinct isn’t crazy. Over long stretches, stocks have historically beaten bonds. I’ve made millions in the market myself.
But Social Security isn’t a long-term investor sitting on its hands. It’s a check-writing machine with a known bill due every month, and it’s already spending down its reserves. That’s the worst possible profile for an all-stock portfolio.
The real fix is the boring one: Congress changing taxes, benefits or both. Until then, keep the risk where it belongs. Stocks are for money that can wait. Social Security is for money that can’t.
Sources: 1. Roll Call Factba.se; 2. Social Security Administration; 3. Social Security Administration (Trust Fund FAQs); 4. NYU Stern (Damodaran); 5. Social Security Administration (Trust Fund Data); 6. 2026 Social Security Trustees Report; 7. 2025 Social Security and Medicare Trustees Report Summary; 8. Social Security Administration (COLA)
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