Legal intrigue swirls over ex-Trump exec Weisselberg: Five key points

Donald Trump’s longtime chief financial officer Allen Weisselberg faces escalating legal jeopardy on multiple fronts over questionable financial activity linked to the former president and the Trump Organization.

Weisselberg is reportedly the subject of a criminal tax probe by the New York attorney general and an overlapping inquiry by the Manhattan district attorney, whose offices have begun coordinating efforts.

The investigative pace seems to have quickened in recent months. Many details still remain unknown, including the breadth of Weisselberg’s potential wrongdoing and the possible evidence he could give to prosecutors on Trump and his business dealings. 

Here are five questions and answers about Weisselberg.

Why are investigators looking at Weisselberg?

In a word: Trump. Prosecutors reportedly aim to “flip” Weisselberg, meaning gain his cooperation as a witness against the former president and his company, who are being looked at for an array of potential financial misconduct including criminal fraud.

As a top Trump executive for four decades, Weisselberg could prove an invaluable source of information.

According to Weisselberg’s former daughter-in-law Jennifer Weisselberg, Trump and his financial chief were virtually inseparable when they worked down the hall from each other on the 26th floor of Trump Tower. She believes her former father-in-law’s testimony would be damning if he cooperates with investigators. 

“You walk down the hall, it’s Allen-Donald, Allen-Donald — they don’t do anything separately,” she told The New Yorker. “Allen would know everything.”

Legal experts say a witness like Weisselberg could be crucial in any future prosecution of Trump or his company, particularly given how difficult it can be to secure a guilty verdict in tax-related cases.

Allen Weisselberg’s attorney, Mary Mulligan of the firm Friedman Kaplan Seiler & Adelman, declined to comment and told The Hill that Weisselberg also declined to comment. Duncan Levin, an attorney for Jennifer Weisselberg, did not immediately respond to a request for comment.

How could he help prosecutors build a case against Trump?

Weisselberg could provide direct evidence of potential crimes and fill in the details of the Trump Organization’s financial picture.

He was one of only several people involved in preparing Trump’s tax returns, according to Michael Cohen, Trump’s former lawyer and fixer who later spoke out against Trump.

One angle prosecutors are reportedly pursuing is whether Trump’s business gave employees benefits instead of higher salaries as a way to lower the company’s payroll tax burden. Among the alleged recipients are Weisselberg himself and his family members, who reportedly received heavily discounted or free access to Trump-owned apartments in Manhattan.

Jennifer Weisselberg told CNN she believes that Trump paid for one of her two children’s tuition to an upscale Manhattan private school that costs $54,000 annually per child (and said Allen paid for the other child). Manhattan District Attorney Cyrus Vance’s office has reportedly subpoenaed the school for tuition payment records.

Tax law generally considers employee perks to be taxable, which companies are responsible for paying. Weisselberg could tell prosecutors the extent to which these fringe benefits went unreported to the Internal Revenue Service (IRS).

Trump, for his part, dismissed the investigations as a partisan “witch hunt,” noting that both offices involved in the probes are led by Democrats.

“These investigations have also been going on for years with members and associates of the Trump Organization being viciously attacked, harassed, and threatened, in order to say anything bad about the 45th President of the United States,” Trump said in a statement.

What other investigative threads are publicly known right now?

Investigators from both Vance’s office and the office of New York Attorney General Letitia James are reportedly looking into whether Trump’s company misled lenders, insurance companies and tax collectors. 

Among the millions of pages of documents in evidence are eight years’ worth of Trump’s tax returns, which Vance’s office obtained in February after a long legal battle.

One theory is that the company inflated the value of assets to get more favorable terms for bank loans, insurance and tax breaks, and deflated their value to reduce the amount owed in real estate taxes.

Investigators are also looking into possible tax fraud related to Seven Springs estate, a New York property in the Trump Organization’s portfolio, as well as hush-money payments to Stormy Daniels, an adult film star who says she had an affair with Trump, which he denies.

Neither of the offices leading the investigations responded to requests for comment.

What are investigators doing to gain Weisselberg’s cooperation?

Weisselberg has not been formally accused of wrongdoing at this point but the growing prospect that he could face criminal charges figures as a key point of leverage for prosecutors.  

Vance’s office in March reportedly subpoenaed records from Weisselberg’s bank, which could signal an escalation in the probe.

Members of Weisselberg’s family also appear to be on investigators’ radar. 

His former daughter-in-law Jennifer is reportedly cooperating with investigators. In April, Vance’s office executed a grand jury subpoena for her financial records, which reportedly date back several decades.

Investigators may also be interested in one of Weisselberg’s two sons, Barry, who worked for the Trump Organization for roughly two decades.

Barry, in a 2018 deposition stemming from his divorce with Jennifer, said his father largely funded the extravagant lifestyle he and Jennifer lived during 14 years of marriage, with Allen reportedly providing for cars, rent, tuition, medical bills and other expenses.

Barbara Res, a former Trump Organization employee, said she thinks Weisselberg is “very concerned” about his children potentially facing legal jeopardy. 

“I don’t think Weisselberg will let his children go to jail,” she told MSNBC.

Would he “flip” on Trump?

The pressure on Weisselberg to flip is mounting. At the same time, though, Weisselberg is seen as fiercely loyal to Trump.

Trump allies have a mixed record when faced with the choice of either sticking by Trump’s side and bearing the full consequences, or turning on him in exchange for leniency.

Some longtime allies of Trump have stayed mum and, rather than flip, faced or served prison time. Those include Roger Stone, former campaign manager Paul Manafort and former national security adviser Michael Flynn. 

But those men kept quiet while Trump was still in the White House, and their silence was later met in the waning days of Trump’s presidency with a pardon.

Weisselberg would not be the first Trump associate to flip. Cohen, Trump’s former attorney, cooperated with former special counsel Robert Mueller’s Russia investigation, as well as New York investigators looking into Trump and his company. 

Cohen said Weisselberg would have to determine “whether or not fealty to Donald Trump means going to prison.” During an MSNBC appearance, he added that prosecutors “have powers that most people don’t understand.”

“When they come at you with the full force of government, you really have no choice but to take the plea, because one, they can financially destroy you,” Cohen said. “And the threat of incarceration is enough in order to get people to start to provide answers and cooperate.” 

Jennifer Weisselberg told CNN this week that she believes he would become a witness against Trump. Previously, however, she was more equivocal, citing Weisselberg’s outsized devotion to the former president.

“His whole worth is ‘Does Donald like me today?’ It’s his whole life, his core being. He’s obsessed. He has more feelings and adoration for Donald than for his wife,” she told The New Yorker for a March article. Asked if would flip, she said, “I don’t know. For Donald, it’s a business. But for Allen it’s a love affair.”