Donald Trump, his former chief financial officer Allen Weisselberg, center, and his son Donald Trump Jr.Mother Jones illustration; Evan Vucci/AP
Allen Weisselberg, the longtime chief financial officer for former president Donald Trump’s company, was sent to jail for five months on Wednesday morning. Weisselberg was taken into custody after pleading guilty to perjury, admitting that he lied under oath during Trump’s civil fraud trial last fall. Weisselberg worked for Trump for more than 30 years, rising from a lowly accountant position to be the man who handled day-to-day financials for the former president’s real estate business and kept his financial records.
This isn’t the first time Weisselberg has been imprisoned in relation to his longtime boss. Last spring, Weisselberg served four months at Rikers Island jail after he plead guilty in 2022 to orchestrating a tax evasion scheme at the Trump Organization. In that case, Weisselberg admitted to trying to reduce his own and other employees’ taxable incomes by shifting salary into fringe benefits—taking less money in pay, in exchange for free rent, luxury cars, and school tuition.
After he plead guilty, the Trump Organization kept him on the payroll, even as he subsequently testified against the company in a trial for its own involvement in the tax fraud. While the company was found guilty and fined $1.6 million, Weisselberg refused to directly implicate Donald Trump personally.
After that Trump Organization’s tax fraud trial was over, Weisselberg signed a separation agreement with the company that included a $1 million payout, and barred him from discussing his work or cooperating with investigators—unless legally required to. Weisselberg had also been named as a defendant in the company’s tax fraud trial and was personally ordered to pay $1 million. Trump has appealed his own judgement for $460 million.
During Trump’s civil fraud trial, where he was accused of lying about how much his properties were worth to get better deals from insurance companies and banks, Weisselberg took the stand to talk about how Trump’s valuations—testimony that led to his newest prison stint. One figure under scrutiny was for Trump’s roughly 10,000 square-foot penthouse in Trump Tower, which Trump had long described as being three times larger than it actually was—and consequently far, far more valuable. Forbes magazine had exposed that as a lie, but at trial, Weisselberg testified that he had never been particularly involved with the discussion over the unit’s valuation. The implication was that the serious discrepancy was not actually an orchestrated attempt by those at the Trump Organization to deceive anyone.
However, reporters at Forbes had recordings, emails, and notes showing that Weisselberg had actually been very involved with valuing the penthouse. In fact, Forbes reported mid-trial, Weisselberg had pestered the magazine’s reporters for years, trying to convince them of how valuable the penthouse was, falsely telling them that it was more than 30,000 square feet. Weisselberg had even tagged along with Trump as he gave Forbes reporters a tour, when Trump repeatedly said it was much larger than it really was, and worth more than it really was.
It’s not clear if Weisselberg will testify in the hush money trial that starts next week in Manhattan, focusing on payments Trump made to adult film star Stormy Daniels, allegedly an effort to cover up their affair. Weisselberg played a key role in the financial machinations surrounding the scheme. With Trump denying the payments were to coverup an affair or in violation of any laws, Weisselberg’s participation would be unlikely to help him.
