Meet Allen Weisselberg, the Trump Organization CFO prosecutors reportedly may charge as soon as this week

• Allen Weisselberg is the Trump Organization's longtime CFO and the Trump family's bookkeeper.
• The Manhattan DA is reportedly trying to "flip" him for its investigation into Trump's finances.
• Weisselberg and his family's close ties to the Trumps go into legal gray areas.

During the past several years of criminal investigations, congressional inquiries, and political battles over Donald Trump's taxes and business dealings, the one man most intimately familiar with them has tried to keep out of the spotlight.

The mustachioed, press-shy Allen Weisselberg has served as the Trump Organization's chief financial officer for decades, as well as Trump's personal bookkeeper. Now he's a subject of a wide-ranging criminal inquiry from the Manhattan District Attorney's office and the New York State Attorney General's office.

Prosecutors are looking to "flip" Weisselberg into cooperating with an investigation into Trump's finances and reportedly may announce charges against him as soon as Monday.

Weisselberg, 73, has served the Trump family since the 1970s and was the only person who's not a member of Trump's family to oversee his trust while he was president.

Given his vast familiarity with the Trump family's finances and its network of companies, Weisselberg could be the most important source for any investigation into Trump's finances. Court filings and public statements suggest prosecutors are examining whether the Trump Organization broke state tax, insurance, and bank laws by misrepresenting property values.

Manhattan prosecutors subpoenaed Weisselberg's personal bank records in an effort to obtain his cooperation, according to the New York Times. They have also zeroed in on Weisselberg's two sons, both of whom have close ties to the Trump Organization.

Jennifer Weisselberg, who was married to Allen Weisselberg's son, Barry, for 14 years and is a cooperating witness in the investigations, told Insider in an interview that prosecutors were looking into flipping her former father-in-law. She said Allen Weisselberg would arrange compensation packages in ways that could allow the Trump Organization to skirt tax rules.

"It was like Allen designing a plan," she said. "It was like, 'OK, the way we're going to maestro this is instead of a raise, we're going to pay my daughter's tuition. Instead of a raise, we're going to pay for the apartment.'"

Mary Mulligan, an attorney representing Weisselberg at Friedman Kaplan Seiler & Adelman LLP, declined to comment for this story.

Allen Weisselberg knows more about the Trump Organization's finances than anyone else

Weisselberg got his start with the Trump family in the 1970s as a bookkeeper for Fred Trump.

Over the years, he ascended the ranks of the Trump Organization to become its chief financial officer, and he has held the keys to the family's financial life as well. (While other reports refer to him as an accountant, Weisselberg does not hold a certified public accountant license, according to New York state records.)

"There's a misconception about the Trump Organization that it's this big, massive company with 10,000 employees," Michael Cohen, Trump's former personal lawyer and an ex-vice president for the Trump Organization, said in congressional testimony. "It's not. I mean, the entire company was really run by 12 of us."

Weisselberg's name made headlines in 2018 and 2019 as federal prosecutors investigated Cohen's hush-money payments ahead of the 2016 election to women who accused Trump of having affairs with them.

Cohen released a tape in which he mentions Weisselberg while appearing to discuss how to facilitate the payments and what they might mean for the Trump Organization. And while Cohen ultimately pleaded guilty to federal crimes in connection with the scheme, The Wall Street Journal reported Weisselberg received immunity for cooperating with the investigators in the Southern District of New York who prosecuted Cohen.

While the Manhattan District Attorney's Office likely has all the documents it needs for its investigation, Jeff Robbins, a former federal prosecutor who oversaw money-laundering investigations, said that having someone like Weisselberg guide it through all the evidence could be enormously helpful.

"I'm sure the records have been turned over by the hundreds and thousands," Robbins told Insider. "However, it sure makes it a lot easier if you have somebody who can walk the prosecutors through the documents and explain the sequence, and who would have had direct conversations with Trump."

Unlike Donald Trump Jr. and Eric Trump, Trump's sons who play leading roles in his company, Weisselberg has made few forays into politics. New York state voter-registration records reviewed by Insider show that he's a registered Republican living in Manhattan's Upper West Side (his building previously carried Trump branding, but it has since been removed), but he didn't donate to any of his boss' presidential campaigns.

But he did donate to two of Trump's political rivals. Federal Election Commission records published by the Center for Responsive Politics showed that Weisselberg donated to Democratic Sen. Chuck Schumer of New York's 2010 campaign and to former Republican Sen. John McCain of Arizona's presidential campaign in 2008. Both donations predated Trump's 2016 presidential campaign, and Trump himself donated to Schumer's campaigns in the 1990s.

Weisselberg also donated to former Illinois Rep. Dan Rostenkowski, a Democrat who led the House's powerful Ways and Means Committee, in 1994. The donation came a month before Rostenkowski was criminally indicted for his role in a corruption scandal that ultimately led to his resignation and a guilty plea on mail-fraud charges.

Weisselberg and his wife have a home in Boynton Beach, Florida, a short drive away from Trump's Mar-a-Lago club. They're involved in a lawsuit with their homeowner-insurance company over damage from 2017's Hurricane Irma.

Allen Weisselberg and Trump often spent time together outside of work, Jennifer Weisselberg told Insider. She said the two would play golf together frequently during Trump's presidency.

She also said the former president could be disrespectful of his personal life. She recounted the incident where Trump first visited Weisselberg's house on Long Island, in the early 2000s. It's was during a shiva, a Jewish mourning ceremony, and Trump showed up in a limousine, disparaged Weisselberg's house, and showed guests photos of him with naked women on a yacht.

"He was just bragging about these pictures," Weisselberg told Insider. "It was just so inappropriate."

His family's financial ties with the Trump Organization go into legal gray areas

The Trumps have always seemed to have a porous wall between their personal finances and their businesses and foundations. In 2019, Trump paid $2 million to settle a lawsuit the New York Attorney General's Office brought. It alleged he used resources from the Trump Foundation to boost his political fortunes.

These legal grey areas appear to extend to Weisselberg and his family, putting them under scrutiny from prosecutors.

In November 2000, according to Bloomberg News, Trump gave a unit at Trump Parc East, a condominium building at 100 Central Park South, to Weisselberg and his wife, Hilary. Records reviewed by Insider showed it had a sale price of $152,500, an eye-poppingly low price for prime Manhattan real estate.

The couple sold it to their son Jack Weisselberg in 2003 for $148,000, who sold it for $570,000 in 2006, Bloomberg News reported.

Jack Weisselberg works as a finance director at Ladder Capital, according to his LinkedIn page. The firm is one of Trump's primary real-estate lenders. It loaned him $280 million to finance four of his Manhattan properties, according to records reviewed by The Wall Street Journal.

Barry Weisselberg, another one of Allen Weisselberg's sons, has even closer and more complicated financial ties with the Trumps. He's an employee at the Trump Organization and had managed the Wollman ice-skating rink in Central Park, which until recently was run by the company through a contract with New York City.

He, too, received an apartment at the Trump Parc East building. According to Bloomberg News, Barry and his now-ex-wife Jennifer Weisselberg received it as a wedding gift in the mid-2000s from Trump and paid only utilities, about $400 a month. When the couple moved out, it was rented out for nearly $5,000 a month, and a Trump-owned entity sold it for $2.8 million in 2014, according to Bloomberg.

But while Barry and Jennifer Weisselberg both lived there, Barry listed it as a corporate apartment in his divorce proceedings, Bloomberg News reported. But their tax returns, according to Bloomberg News, didn't always list the apartment as a corporate perk. The designation may mean that Barry Weisselberg and the Trump Organization itself may have not paid the correct amount of taxes on the apartment, Bloomberg's Caleb Melby reported.

That apartment - and its tax ramifications - are a subject of Manhattan District Attorney Cyrus Vance Jr.'s investigation, according to The Washington Post.

"On the question of where Allen Weisselberg stands in the evidence pyramid, he stands right below Donald Trump himself," Robbins, now an attorney at Saul Ewing Arnstein & Lehr, told Insider. "So it does appear to be an exploration on the part of the DA's office as to whether or not they can flip Allen Weisselberg by leveraging one of his two sons."

The Manhattan District Attorney's office is trying to flip him

Jennifer Weisselberg told Insider her former father-in-law further intertwined their finances by managing their family's. She said prosecutors took "seven boxes of documents" from her divorce from Barry Weisselberg, which included pages of Trump Organization financial information.

The Manhattan District Attorney's Office sent a forensic accountant with experience analyzing mob finances to review the documentation, Jennifer Weisselberg said. Prosecutors may be able to tell whether Allen Weisselberg distorted the Trump Organization's financial picture by comparing payroll information and tax filings among Jennifer Weisselberg's documents to the documents the Trump Organization filed with the IRS and state tax authorities.

Prosecutors have also pressured Weisselberg on a personal level. In addition to subpoenaing his personal financial information, they have subpoenaed information from the school his grandchildren attend, which will permit them to see who paid for the tuition and whether such benefits were taxed appropriately.

The investigation into the Weisselbergs grew out of Vance's investigation into the Trump Organization's business dealings with other companies, including Deutsche Bank and Ladder Capital. Jack Weisselberg is also a subject of the probe, though it's unclear if he had any role in loans Ladder Capital gave to the Trump Organization, according to Bloomberg News.

The Trump Organization also gave Barry Weisselberg an Upper East Side townhouse while he was in the divorce process in 2018, Bloomberg News reported. It isn't clear how Weisselberg and the Trump Organization treated it in tax filings.

While Allen Weisselberg seems to have been loyal to the Trump family for years, Robbins said the pressure on his family could flip him.

"The likelihood of him cooperating goes up significantly if, in fact, the prosecutors have criminal charges that can reasonably be brought against his sons," Robbins said. "For the simple human reason that what father would not do something unpleasant in order to help his sons out of a legal jam?"

Apartments seem to be a common perk for Trump employees. Cohen also had an apartment in one of Trump's buildings while working for the mogul, and former White House Communications Director Hope Hicks stayed in one "rent-free" during Trump's 2016 campaign, according to The Times. Matthew Calamari, Trump's longtime head of security, also has a home in the Trump Parc East building, according to records reviewed by Insider.

A source familiar with the operations of the Trump Organization said perks like free rent, tuition, car payments, and club memberships were common among top executives at the company.

Jennifer Weisselberg told Insider that the Trump Organization would offer such perks to key employees as a way of controlling them. She said her ex-husband Barry Weisselberg's salary hardly changed in the 20 years he worked for the company, and he was instead compensated by having his apartment paid for and by the Trump Organization paying for things like his kids' tuition.

"They want you to do crimes and not talk about it and don't leave," she said.

"It's so controlling," she added. "Because if you want to leave and make the same money - you live there. If you want to leave, where are you going to live?"

Jack Weisselberg and representatives for Ladder Capital didn't immediately respond to Insider's requests for comment. Barry Weisselberg couldn't be reached for comment.

He's cooperated with prosecutors in the past

Weisselberg's name hasn't been particularly important in the Manhattan district attorney's court battles over Trump's tax records. But he has played a role in different investigations from federal and state prosecutors.

The chief financial officer testified for federal prosecutors in Manhattan who secured Cohen's guilty plea. Weisselberg helped the Trump Organization reimburse Cohen the $130,000 hush-money payment he made to Stormy Daniels, the adult-film actress who said she had sex with Trump during Melania Trump's pregnancy.

Weisselberg's name didn't appear in the charging documents against Cohen, and he was never charged for his participation in the scheme.

Cohen hasn't forgiven Weisselberg. When the news broke that prosecutors were looking into Weisselberg's family, he spoke out on Twitter.

"Remember that Allen Weisselberg received (federal) immunity from the SDNY to provide information and testify against me for the @StormyDaniels payment. #KarmaBoomerang," Cohen wrote.

In a separate investigation, for Trump's now defunct charity foundation, Weisselberg testified for prosecutors working for New York Attorney General Letitia James.

Weisselberg told prosecutors he had little knowledge of the Trump Foundation's operations and testified he had no knowledge that he was on the Trump Foundation's board of directors in a deposition transcript reviewed by Insider.

But he did testify that the foundation was used to boost Trump's campaign in 2016. James' office used the testimony in its lawsuit against the Trump Foundation, and a judge forced Trump to pay a $2 million fine.

Weisselberg's vast knowledge of Trump's finances has made him a target in civil lawsuits as well.

He was a defendant in a 2017 lawsuit from William Weinstein, a New York resident who sought to create a mechanism to ensure that Trump wouldn't take foreign profits as president through the Trump Organization. It was dismissed in short order, with the judge ruling that Weinstein didn't have the standing to sue. Trump has steadfastly refused to release financial records, and The New York Times reported Trump had paid far more in foreign taxes over the past two decades than in US taxes.

He's been less helpful in an ongoing investigation from the New York AG

Weisselberg also testified in a different ongoing investigation into Trump's finances from James' office, sitting for a deposition under subpoena in July and August 2020.

In that case, he was less forthcoming.

A court filing from the New York Attorney General's Office suggested Weisselberg was questioned about the tax categorization of forgiven loans to the Trump Organization, but that he wasn't very helpful.

"When examined by OAG, however, Mr. Weisselberg testified that he had no first-hand knowledge of this fact, had not reviewed the relevant documents to confirm that any such understanding was true, could not identify any return on which the forgiveness was treated as income, and instead was relying solely upon his recollection of conversations he had years earlier with the Trump Organization's accountants concerning the tax treatment of the amount of the debt that was forgiven," the filing said.

The Trump Organization refused to furnish the relevant tax documents, attorneys for the attorney general's office wrote in the filing.

Weisselberg was similarly unhelpful when asked about Seven Springs, a property in upstate New York that Trump has treated as a tax write-off for nature conservation, according to The Washington Post, even though family members have said it's a personal residence.

The lack of information Weisselberg gave in his testimony led the attorney general's office to subpoena the Trump Organization for its tax documents, prosecutors wrote.

Since then, the Manhattan District Attorney's Office successfully won two Supreme Court battles to obtain Trump's tax documents. In May, the New York Attorney General's office announced it was joining forces with the Manhattan district attorney, and that its inquiry would be criminal in nature.

This article has been updated.