Donald Trump’s longtime chief financial officer, Allen Weisselberg, faces a tax fraud conviction

NEW YORK CITY– Allen Weisselberg, a longtime manager of Donald Trump’s real estate empire whose testimony helped convict the former president’s firm of tax fraud, is scheduled to be convicted on Tuesday of tax evasion for $1.7 million in work benefits.

New York judge Juan Manuel Merchan Weisselberg, a senior adviser to the Trump Organization and former chief financial officer, is expected to be sentenced to five months in prison under a settlement reached in August.

Weisselberg, 75, was promised that sentence when he agreed to plead guilty to 15 tax offenses and testify against the company he had worked for since the mid-1980s.

When he begins his sentence, Weisselberg is expected to be incarcerated in New York’s notorious Rikers Island prison complex. He can be released after just over three months if he behaves behind bars.

As part of his plea agreement, Weisselberg must also pay nearly $2 million in taxes, penalties and interest, which he said he has made significant progress in paying. He must also complete a five-year probationary period.

Weisselberg faced up to 15 years in prison — the maximum penalty for the highest grand larceny charge — if he failed to honor the deal or if he failed to testify truthfully at the Trump Organization trial. He is the only person charged in the Manhattan District Attorney’s three-year investigation into Trump and his business practices.

Weisselberg testified for three days and gave a glimpse into the inner workings of Trump’s real estate empire. Weisselberg has worked for Trump’s family for nearly 50 years, starting as an accountant for his developer father Fred Trump in 1973 before joining Donald Trump in 1986 and helping expand the family business’s focus beyond New York City into a global golf and hotel brand.

Weisselberg told jurors he betrayed the Trump family’s trust by conspiring with a subordinate to hide more than a decade’s worth of extras from his income, including a free Manhattan apartment, luxury cars and his grandchildren’s private school tuition . He said they forged pay slips and issued fake W-2 forms.

A Manhattan jury convicted the Trump Organization in December, finding that Weisselberg had been a “senior” agent assigned to act on behalf of the company and its various entities. Weisselberg’s arrangement reduced his own personal income taxes, but also saved money for the company by not having to pay him more to cover the cost of the perks.

Prosecutors said other Trump Organization executives also accepted unscheduled compensation. Weißelberg alone has been accused of defrauding the federal, state and local government out of more than $900,000 in unpaid taxes and unearned tax refunds.

The Trump Organization is scheduled to be convicted on Friday and face a fine of up to $1.6 million.

Weisselberg testified that neither Trump nor his family knew about the plan while it was happening, and choked as he told the jury, “It was my personal greed that led to it.” But prosecutors said in their closing argument, Trump “knew exactly what was going on,” and that evidence, such as a lease he signed on Weisselberg’s apartment, made it clear that “Mr. Trump specifically sanctions tax fraud.”

A Trump Organization lawyer, Michael van der Veen, said Weisselberg hatched the plan without the knowledge of Trump or the Trump family.

Weisselberg said the Trumps have remained loyal to him even as the company struggled to end some of its dubious wage practices after Trump’s 2016 election. He said Trump’s eldest sons, who have been trusted to run the company while Trump was president, gave him a $200,000 pay rise after an internal audit found he had cut his salary and bonuses to reflect the cost of the perks .

Although he is now on leave, the company continues to pay Weisselberg a $640,000 salary and $500,000 in vacation pay. It fined him only nominally after his arrest in July 2021, reassigned him to senior counsel and relocated his office.

He even celebrated his 75th birthday at Trump Tower with cake and colleagues in August, just hours after he finalized the settlement agreement that began his transformation from loyal executive to prosecution witness.

Rikers Island, a cluster of 10 jails on a promontory in the East River just off the main runway at Queens’ LaGuardia Airport, has been plagued by violence, inmate deaths and dire staff shortages in recent years.

Though it’s only five miles from Trump Tower, it’s a true world away from the luxury living Weisselberg wanted to build — a far cry from the gilded offices on Fifth Avenue where he hatched his property and the apartment overlooking the Hudson River, which he reaped as a reward.