He is Donald Trump’s ‘eyes and ears’. Can prosecutors persuade him to talk?

Allen Weisselberg the ‘skeleton key’ uniquely capable of unlocking finances of Trump family business

For Allen Weisselberg, the Trump Organization has not just been a job for the past 48 years. It has been a life – and his family's life, too.

Weisselberg (73), the company's long-serving chief financial officer, was hired as a bookkeeper by Fred Trump, the patriarch, soon after graduating from college. Over decades, he served Fred's son, Donald, as the restless heir dragged the family business into Manhattan and then nearly wrecked it in Atlantic City.

On evenings after work – and sometimes early in the morning – he would drop by a Trump-owned apartment overlooking Central Park to visit his son, Barry, who worked for the Trumps managing the nearby Wollman skating rink until the city cancelled the contract this year.

Another Weisselberg son, Jack, is at a short remove: he is an executive at Ladder Capital, a property firm that was started after the 2008 financial crisis and soon became one of the biggest lenders to the Trump Organization. Allen's sister-in-law, Stacy, also works for the Trumps in the insurance department at Trump Tower on Fifth Avenue.


So trusted is Weisselberg by the family that he was tapped to run the company alongside the elder Trump sons when Donald went to the White House.

Now, the legal question haunting the former president and his business empire is whether Weisselberg, who once described himself as Trump’s “eyes and ears”, will break that trust, and betray the family to whom he has devoted his adult life?

Out of office, and shorn of the protection of the presidency, Trump faces legal peril on multiple fronts. In Georgia, prosecutors have launched separate investigations into his apparent attempt to overturn the November election when he badgered the state's top election official in a January phone call to "find" more votes for him. In Washington, local and federal prosecutors are examining whether the former president can be tried for his role in instigating the January 6th insurrection on Capitol Hill.

But the most dire threat may be the criminal investigation by Cyrus Vance, the Manhattan district attorney. It began in 2018 in response to reports that Trump's former fixer, Michael Cohen, had made $130,000 in hush money payments to a former adult film actor who claimed to have had an extramarital affair with Trump. It has since evolved, according to court filings and people briefed on the matter, to focus on possible banking and insurance fraud at the Trump Organization.

‘Witch hunt’

In particular, Vance and his team are exploring whether the company committed fraud by knowingly inflating the values of some properties to secure bank loans or insurance on favourable terms while understating them to minimise taxes. Trump has dismissed that probe – and a parallel, civil investigation by the New York attorney general, Letitia James – as a partisan "witch hunt".

Weisselberg is regarded as a skeleton key uniquely capable of unlocking the complicated finances of the family business. “Not one penny came into the Trump Organization, or went out of the Trump Organization, without it crossing Allen Weisselberg’s desk,” says Cohen, who was sentenced to three years in prison for crimes stemming from the hush money payments.

Authorities have stepped up their scrutiny of Weisselberg and some of his family members in recent months in what former prosecutors say looks like an attempt to force his co-operation. He could prove valuable on a witness stand, say legal experts, guiding a jury through a case that might otherwise rely on the drudgery of accounting ledgers. As Trump’s numbers man, he could also speak to the intentions of a boss who did not use email and seldom put his orders in writing.

"They need witnesses to connect those dots," says Daniel Horwitz, a former prosecutor in the Manhattan DA's office who now leads the white collar practice at McLaughlin & Stern.

Persuading him to switch sides, according to Horwitz, is less a prosecutorial art than a matter of cold calculation. “The analysis is the same for anybody who’s being pressured to flip,” he says, “and that is: what is their tolerance for bad consequences if they don’t flip?”

Some legal observers are sceptical. "I would have expected flipping Weisselberg to be an uphill battle," says Daniel R Alonso, who served as Vance's top assistant and now practises at the financial law firm Buckley, noting that New York state law tends to be less frightening for defendants than federal law. "If I had to speculate, I'd say he doesn't flip based on his own liability. But that could of course change if his family members are in jeopardy."

Unlikely figure

So attuned to the Trumps is Weisselberg, says a person who knows him, that he gave up drinking out of respect for Donald, whose brother, Fred Jr, died of alcoholism in 1981. Another described him as a "Donald Trump soldier" who would "walk through fire" for his boss. "In order to be there forever you have to have undying, total loyalty that transcends human comprehension," this person explains.

But for Weisselberg, the analysis may be shifting, thanks to an unlikely figure: his former daughter-in-law, Jennifer.

She has been engaged in a bitter divorce fight with Barry Weisselberg that began in 2017, losing custody of their two children in the process, which she is contesting.

In recent days Jennifer has handed over three boxes of personal financial records to Manhattan district attorney investigators, and has hired a forensic accountant to review others for possible evidence. “She has a number of financial documents they’re interested in,” says her lawyer, Duncan Levin.

One item to emerge from her divorce is that the apartment on Central Park South where she and Barry lived rent-free for several years after their 2004 wedding was still owned by the Trump Organization – unbeknown to Jennifer, who believed it had been a wedding gift to the couple. That has raised the question of whether appropriate taxes were paid on the property – by the company or the couple.

In an interview, Jennifer explains that compensating employees through other means – be it cars or paying her children’s $49,000-a-year private school tuition – was a standard Trump practice orchestrated by Weisselberg. It allowed the company to minimise taxes while enforcing loyalty.

“When you start working there and they pay for your house and your cars, it’s a lifestyle,” she says. “That’s how they pay, and it controls you.”

Cash receipts

Investigators from the DA’s office have asked Jennifer about Barry’s work at Wollman Rink, and appear to be interested in how its cash receipts were handled, according to Levin. They have also inquired about Jack’s work at Ladder Capital.

The firm arranged a $100 million loan for Trump Tower in 2012 and a $160 million loan for 40 Wall Street in 2015. At the time, other lenders – with the exception of Deutsche Bank – shunned Trump after his string of bankruptcies. Jack Weisselberg and Ladder Capital declined requests for comment.

More broadly, says Jennifer, “a very big part” of the questions investigators posed to her concerned “the control [Weisselberg] exhibits both at work and outside of work”.

Weisselberg has not been accused of any crime and it is far from clear whether he – let alone Trump – ever will be. Accounting cases are notoriously difficult to prove to a jury. To take the potentially explosive step of bringing charges against a former president would require a robust case – not a mere technicality, say former prosecutors. Weisselberg declined requests for comment for this article.

Vance’s window to bring charges is closing because he is leaving office at the end of the year.

Still, some believe they glimpsed the DA's intentions in February when Mark Pomerantz, a seasoned former prosecutor who helped take down the Gambino crime family, left private practice to assist Vance.

"Would you do that if you were coming over for a BS [bulls**t] investigation that's not going anywhere? Would you want to quit your job and be associated with that? Probably not," says one former official from the DA's office. Michael Bachner, a New York defence lawyer, called Pomerantz's hiring "a very aggressive tell by Vance".

Numbers man

Like his longtime boss, Weisselberg grew up in an outer borough of New York – in his case, the Brownsville neighbourhood of Brooklyn. He graduated from Pace College in 1970 with an accounting degree.

Even as his fortunes rose, he and his wife lived for years in a modest ranch house in Wantagh, Long Island – which Trump once mocked at a shiva, a Jewish mourning ritual, according to Jennifer – before finally moving to a Trump building in Manhattan.

One of the rare occasions when the balding, bespectacled Weisselberg emerged from behind the curtain of the Trump Organization was his appearance as a judge on a 2004 episode of The Apprentice, the reality television programme that helped launch Trump’s political career.

"If this was a military manoeuvre and he lost his line of communication, he could lose an entire battalion," he remarked, sounding like second World War US general George Patton by way of Brooklyn, as he assessed one contestant's attempt to lead a pet massage business.

Behind the scenes, Weisselberg was an indispensable numbers man whose office was beside Trump’s on the 26th floor of Trump Tower. “He knew the business probably better than anybody when it came to numbers and performance,” one former colleague recalls. “It was always: get Allen in here! He knows the numbers.”

Over the years, he served on the board of the Trump-owned Miss Universe Organization, was the treasurer of the Trump Foundation, the former president's scandal-plagued charity, and oversaw finances for the now shuttered Trump University, which paid a $25 million settlement to aggrieved students.

In his book Think Like a Billionaire, Trump recalled how Weisselberg stood by him during his struggles in the early 1990s, when his casino empire was teetering and banks were threatening to cut off funding. Weisselberg dutifully set about renegotiating the company’s payments.

“He did whatever was necessary to protect the bottom line – and refused to succumb to the pressures of risk,” Trump wrote, calling Weisselberg “a loyal employee” and “the ultimate master at playing the cards of business”.

‘Bigger buildings’

A New York property executive who has long known Weisselberg described him as “sort of the prototypical Trump executive” – one who understood that loyalty was the paramount virtue, and secrecy was a part of the bargain.

His tenure also attests to another truth about the Trump Organization: in spite of the world-conquering image it cultivates, it remains in many ways the same Queens shop Fred Trump founded. While other New York property dynasties have become more professional and institutional over the generations, Trump has not.

“He may have built bigger buildings, but he never built a bigger organisation,” the executive says of Trump. “The truth is he ran his father’s business. It’s all in the family, keep the families close, keep people forever. People who are loyal will do what you tell them to.”

The Weisselbergs are one of a handful of families in the upper echelons of the company. There is Matthew Calamari, a security officer who Trump recruited after watching him tackle a trespasser at the 1981 US Open tennis tournament. He eventually became head of operations. His son, Matt Jr, works in security and his brother, Michael, manages construction.

There is Jeffrey McConney, the financial controller, whose son Justin guided Trump's entrée to social media. There is Deborah Stellio, and her late husband, Vincent, who – among other chores – helped Trump manage the local politicians when the boss pushed to rename a street beside his Los Angeles golf course.

“It’s all in the family,” Jennifer says, of a universe where Trump is the sun, no one ever dares outshine him, and part of the reward for success is more time with Trump – on his private jet, on a Trump golf course or at his Mar-a-Lago club in Palm Beach. Her introduction came during her first date with Barry, who, she said, took her to lunch with his father at Trump Tower. “This is not a regular business,” she concludes. “These people aren’t regular business people. It’s a mess.”

Hush money

In an interview with the Financial Times, Cohen recalls his former colleague as respected in the company, but not necessarily liked. Asked what motivates Weisselberg, Cohen replies: “A job. A job that was far greater than what he should have been able to attain, and so keeping that job was the single most important thing to him.”

Testifying before Congress in 2019, Cohen mentioned Weisselberg more than 20 times as he provided a glimpse of one of the trickier assignments carried out by the Trump Organization's chief financial officer.

It was Weisselberg, he claimed, who contrived to reimburse him for the hush money payments by having the Trump Organization pay him a separate monthly fee it recorded as legal expenses. “Allen Weisselberg made the decision that it should be paid over the 12 months so that it would look like a retainer,” Cohen explained to legislators.

A brief shudder went through Trump observers three years ago when it was reported that Weisselberg had been granted limited immunity from the US attorney’s office for the southern district of New York in order to testify in the hush money investigation. Many interpreted his co-operation with federal prosecutors as Weisselberg having, at last, flipped on his boss.

It now appears that Weisselberg’s testimony was squarely aimed at Cohen – a man who once vowed that he would “take a bullet” for Trump before ultimately turning against him.

Now out of prison, and cast out of Trump world, Cohen says of his erstwhile rival for Trump’s affections: “He has talents. He’s been doing this for over four decades.” – Copyright The Financial Times Limited 2021