Trump’s Social Security Head Is Getting a Massive Tax Break
As Donald Trump works to undermine the Social Security Administration, his ultrarich Social Security commissioner, Frank Bisignano, was just approved for a giant tax break on a $484 million capital gains sale.
Frank Bisignano, commissioner of the Social Security Administration, during a Senate Finance Committee confirmation hearing in Washington, DC, on Tuesday, March 25, 2025. (Daniel Heuer / Bloomberg via Getty Images)
As the Trump administration hollows out the country’s safety net for retirees and those with disabilities, the agency’s new chief has just been approved for a massive tax break for his Wall Street riches, according to new ethics documents reviewed by the Lever.
Frank Bisignano, who ranked as one of Wall Street’s highest-paid CEOs as the head of banking technology company Fiserv, was confirmed as the Social Security Administration chief this month. He will now take the reins at the chronically underfunded agency, which his former company could benefit from privatizing.
To comply with federal ethics law, Bisignano has agreed to sell his shares in Fiserv, which are currently worth roughly $484 million. Because of a special loophole in the tax code for government officials, Bisignano will be able to indefinitely defer any capital gains tax on the divestment — meaning he may never have to pay taxes on the enormous windfall.
The exact value of Bisignano’s tax break is not clear from the ethics disclosure, but previous tax breaks for comparable divestments have been worth tens of millions of dollars.
More than 70 million Americans receive regular retirement and disability benefits through the Social Security Administration, an essential lifeline for retirees.
The agency has been plagued by funding issues for years and now faces new threats from Elon Musk and President Donald Trump. The Trump administration has eliminated three thousand employees at the agency and could soon deliver additional cuts. At the same time, the agency is contending with Department of Government Efficiency (DOGE) investigations into purportedly widespread Social Security fraud, which have so far turned up very little evidence of wrongdoing.
Wall Street has long wanted to privatize Social Security so it can profit from Americans’ retirement savings. Some Democratic lawmakers have warned that Bisignano’s appointment to run the agency represents a significant step toward privatization. His company, which owns a suite of financial technologies, could benefit if the agency chooses to outsource its back-end technology or other services to the firm.
Bisignano will now get a tax break too.
Other affluent Trump administration appointees, who comprise perhaps the wealthiest presidential cabinet in history, stand to benefit from the same tax loophole, which was inserted in the tax code in the 1990s to allow government officials to avoid a tax burden when they divest business interests that pose a conflict of interest. That includes billionaire banker Howard Lutnick, the incoming secretary of commerce, who has been approved to divest hundreds of millions of dollars worth of shares in more than a dozen assets, as Bloomberg reported last month.
In the new documents, which were issued on Wednesday by the Office of Government Ethics, the independent federal ethics agency, Bisignano was granted approval to divest his nearly three million shares in Fiserv, currently valued around $484 million. Additionally, he will divest more than 150,000 shares in the company held by his wife and in family trusts, currently worth an estimated $25 million.
Typically investors must pay capital gains tax on stock sales. But the tax loophole allows Bisignano to sell off his hundreds of millions of dollars in Fiserv without paying a cent.
As Richard Painter, former White House ethics lawyer and University of Minnesota law professor, explained, this is because the loophole allows government officials to buy new assets with the proceeds from a divestment, effectively deferring the tax.
“You only pay the capital gains tax when you sell the new conflict-free assets — if you ever sell them,” Painter wrote in an email to the Lever on Friday. “Great way to diversify tax-free!”
Back in 2006, Goldman Sachs chair Henry Paulson received his own massive tax break through the same loophole when he was appointed Treasury secretary under the second George W. Bush administration.
Paulson divested from his $490 million stake in the investment banking firm upon taking the job, avoiding a capital gains tax that was estimated at the time to be in the tens of millions of dollars.
In theory, Paulson would have had to pay that tax when he eventually sold the stock he purchased with the sale proceeds. But it’s not clear if he ever did.