Ex-Trump CFO Allen Weisselberg begs for leniency as he's sentenced to 5 months for Trump Org tax fraud

• Top Trump money man Allen Weisselberg is sentenced to five months in Trump Org tax-dodge scheme.
• He testified in a monthlong tax crimes trial against the Trump Organization, which was found guilty.

A Manhattan judge on Tuesday sentenced Allen Weisselberg, Donald Trump's longtime chief financial officer, to five months in jail for running a complex and lengthy payroll-tax fraud scheme at the former president's company, the Trump Organization.

"The entire case was driven by greed," said the judge, New York Supreme Court Justice Juan Merchan, in imposing sentence.

Asked to speak in court on his own behalf, Weisselberg appeared to choke back tears as he echoed an earlier plea for leniency by his defense attorney, Nicholas Gravante, Jr.

"I think the words expressed by Mr. Gravante expressed my thoughts and my feelings," Weisselberg, 75, told the judge, his voice breaking.

"It has been difficult."

Weisselberg appeared in court wearing not his typical crisp business suit, but an olive green fleece jacket and blue sweatpants.

His client meant no disrespect, Gravante told the judge.

"He is dressed the way he is because he expects to be remanded today and wanted to appear in the appropriate clothes," the lawyer explained.

With good behavior, Weisselberg's time in Rikers, the city's notoriously violent and chaotic jail, will be cut to roughly 100 days, his lawyer has said.

Weisselberg had been promised a five-month sentence when he pleaded guilty in August to 15 felony counts — including scheme to defraud, conspiracy, grand larceny, and criminal tax fraud — first brought by the Manhattan district attorney's office in July 2021.

The plea deal required Weisselberg to testify truthfully against his company about masterminding the tax-dodge scheme, which saved hundreds of thousands of dollars in taxes for him and a small group of other second-tier Trump Org executives.

The plea deal also required Weisselberg to pay back more than $2 million in back taxes and penalties.

Both conditions have been met, said Susan Hoffinger, one of two lead Manhattan prosecutors at the Trump Organization trial, which ended in conviction last month.

"In Manhattan, you have to play by the rules no matter who you are or who you work for," Manhattan District Attorney Alvin Bragg said in a press statement issued after the sentencing.

"Trump Organization Chief Financial Officer Allen Weisselberg used his high-level position to secure lavish work perks such as a rent-free luxury Manhattan apartment, multiple Mercedes Benz automobiles and private school tuition for his grandchildren – all without paying required taxes," Bragg said in the statement.

In imposing sentence, the judge said he'd originally approved a five-month plea deal, rather than the six-month jail term first requested by prosecutors, because Weisselberg is a former city school teacher and a military veteran.

But after presiding over the Trump Organization trial, he now realizes Weisselberg deserves "a sentence much greater than that," the judge said, without specifying how much greater.

Merchan singled out the greed the then-CFO showed in once cutting a $6,000 Trump Organization paycheck for his wife — who had never worked a day for the company.

Weisselberg told jurors he gave his wife the check so she could get on Social Security.

"Perhaps nothing spoke more loudly to that greed than the $6,000 payment," Merchan said.

Weisselberg's wife and two sons did not appear in court.

"He deeply regrets the lapse in judgement that resulted in his conviction and regrets it most because of the pain that it caused his loving wife, his sons and wonderful grandchildren," Gravante said after the sentencing.

Over the course of the scheme, Weisselberg admittedly enjoyed some $900,000 in tax savings from taking large portions of his salary in the form of untaxed perks, including luxury apartments and cars, and even tuition for his grandchildren.

Under the terms of the plea agreement, Weisselberg will also serve five years of probation.

Along with charges against Weisselberg, the Manhattan district attorney's office brought charges against the Trump Corporation and the Trump Payroll Corporation, two of the entities that comprise the Trump Organization.

As part of his plea deal, Weisselberg took the stand for three days in the trial against the corporate entities, which took place in a lower Manhattan courtroom between late October and early December.

The former president and his family members weren't personally charged, although the district attorney's investigation into the Trump Organization is ongoing, Bragg has said.

Weisselberg's plea came after months of pressure from the Manhattan district attorney's office.

Hanging over him was the specter of charges against his son, Barry Weisselberg, who also worked for the Trump Organization and had tuition bills for his kids comped by the company.

Jeff McConney, the company's controller, previously testified before the grand jury, which immunized him from criminal charges.

But when Weisselberg took the stand at the Trump Organization's trial, he was less than forthcoming, jurors found in their decision to find the company guilty.

"He has a half a million reasons to kind of shade the truth towards their side of the room," Assistant District Attorney Joshua Steinglass told the jury, a reference to a $500,000 year-end bonus Weisselberg had hoped to pocket this month, on top of his $1.14 Trump Organization pay package for 2022.

The question of Weisselberg's allegiance — to the Trump Organization or to the truth — had raised the possibility that Merchan could revoke the plea deal.

A separate sentencing hearing, for the Trump Corporation and the Trump Payroll Corporation, is scheduled for Friday.