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Allen Weisselberg, former Trump Org. CFO, sentenced to 5 months in jail

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New York
CNN
 — 

Allen Weisselberg, former President Donald Trump’s long-time chief financial officer, was sentenced by a New York judge to five months in jail for his role in a decade-long tax fraud scheme after testifying as the state’s witness against the Trump Organization.

Following the court hearing, Weisselberg, 75, is expected to report to Rikers Island, the notorious New York City jail, to begin serving his sentence immediately.

He pleaded guilty last August to 15 felonies in a deal with prosecutors. As part of the deal, he was required to testify truthfully at the trial of the Trump Organization, pay $2 million in back taxes, interest and penalties, and waive any right to appeal.

Weisselberg admitted he should have paid taxes on off-the-books compensation, totaling roughly $200,000 in one year, which included a luxury Manhattan apartment overlooking the Hudson River, two Mercedes Benz car leases, parking, utilities, furniture and private school tuition for his grandchildren.

Judge Juan Merchan on Tuesday said had he not already promised a five-month sentence to Weisselberg, he would have issued a stiffer sentence “much greater” than five months after listening to evidence at trial.

Without a deal, Weisselberg faced a sentence as long as five to 15 years in prison. With credit given for good behavior, one-third of Weisselberg’s sentence could be knocked off, meaning he could end up serving about 100 days behind bars.

Merchan found Weisselberg’s fabrication of a fraudulent $6,000 payroll check cut to his wife so she could become eligible for Social Security benefits to be the most “offensive” of the crimes the judge said were driven by the Trump Org. executive’s greed.

Merchan said he felt he had to share this view in response to Weisselberg’s lawyer who requested an even lesser sentence to his client given his age and other factors.

The long-time Trump Org. executive fulfilled the conditions of his plea agreement, a prosecutor for the Manhattan District Attorney’s Office told the court before Merchan issued the sentence. Prosecutors said that Weisselberg testified truthfully against two Trump companies convicted in connection to the tax fraud scheme in December, prosecutor Susan Hoffinger said.

Weisselberg also paid off the remaining balance of just over $1 million in back taxes and penalties last week he owed to tax authorities, Hoffinger confirmed. He paid more than $2 million in total.

Weisselberg’s attorney Nicholas Gravante said Tuesday “is obviously a difficult day for him, but it is a day for which he has been preparing for many months, since he entered his plea last August.”

“Mr. Weisselberg came to court today ready to begin his sentence, and he is grateful that it has now begun,” Gravante said. “He deeply regrets the lapse in judgment that resulted in his conviction, and he regrets it most because of the pain it has caused his loving wife, his sons and wonderful grandchildren.”

New York District Attorney Alvin Bragg said that the plea and sentence shows that, “in Manhattan, you have to play by the rules no matter who you are or who you work for.”

“Now, he and two Trump companies have been convicted of felonies and Weisselberg will serve a jail sentence for his crimes,” Bragg added.

The sentencing caps one long-running investigation – but it comes as the Manhattan district attorney’s office continues to investigate the Trump Organization. Prosecutors are conducting a wide-ranging investigation involving the accuracy of the companies’ financial statements, and in recent months its focus has returned to the company’s involvement in hush-money payments made to silence adult film star Stormy Daniels from going public with an affair with Trump just before the 2016 election, people familiar with the matter said. Trump has denied the affair.

Weisselberg’s legal woes are not over. He is also a defendant in a $250 million civil lawsuit brought by New York Attorney General Letitia James, who has alleged Trump, his three eldest children, Weisselberg and others defrauded lenders, insurers and tax authorities by inflating the value of multiple Trump Organization properties for more than a decade. Trump has denied wrongdoing and said the lawsuit is politically motivated.

In his testimony at the Trump Organization’s tax fraud trial late last year, Weisselberg said he conspired with others at the company and described conversations he had with Trump, sons Eric Trump and Donald Trump Jr., but told the jury when questioned by Trump attorneys that he did not scheme or conspire with anybody in the Trump family.

Last month, after a few hours of deliberations, two Trump Organization entities were convicted on multiple charges of tax fraud and falsifying business records. Lawyers for the entities said they will appeal.

A source close to the situation said as of Tuesday, Weisselberg is no longer an employee of the Trump Org., describing it as an amicable separation with a severance.

This story has been updated with additional details.

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Trump executive Weisselberg prepares for jail on Rikers Island

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NEW YORK, Jan 10 (Reuters) – A longtime executive for Donald Trump is expected to be sent to New York’s notorious Rikers Island jail after being sentenced on Tuesday for helping engineer a 15-year tax fraud scheme at the former president’s real estate company.

Allen Weisselberg, the Trump Organization’s former chief financial officer, pleaded guilty in August, admitting that from 2005 to 2017 he and other executives received bonuses and perks that saved the company and themselves money.

Weisselberg is expected to be sentenced to five months behind bars, after paying nearly $2 million in taxes, penalties and interest and testifying at the criminal trial of the Trump Organization, which was convicted on all counts it faced.

The sentence will be imposed by Justice Juan Merchan, who oversaw the trial in a New York state court in Manhattan. Weisselberg would likely serve 100 days with time off for good behavior.

Those days will probably not be easy for Weisselberg, 75, at a jail known for violence, drugs and corruption. Nineteen inmates there died last year.

“You’re going into a byzantine black hole,” said Craig Rothfeld, a prison consultant helping Weisselberg prepare for lockup.

50-YEAR RELATIONSHIP

Many convicts in New York City facing one year or less behind bars head to Rikers Island, which lies between the New York City boroughs of Queens and the Bronx and houses more than 5,900 inmates.

Rothfeld spent more than five weeks at Rikers in 2015 and 2016 as part of an 18-month sentence for defrauding investors and tax authorities when he was chief executive of the now-defunct WJB Capital Group Inc.

He now runs Inside Outside Ltd, which advises people facing incarceration. Another client is Harvey Weinstein, the former Hollywood movie producer convicted twice of rape.

After being sentenced, Weisselberg will likely be driven to Rikers and trade his street clothes for a uniform and sneakers with velcro straps.

Rothfeld said he hopes Weisselberg will be segregated from the general population, and not placed in a dorm with inmates who may not know him but will know his boss, who is seeking the presidency in 2024.

“Certainly Mr. Weisselberg’s 50-year relationship with the former president is on all our minds,” Rothfeld said.

A spokesman for the city’s Department of Correction said the agency’s mission is “to create a safe and supportive environment for everyone who enters our custody.”

Rikers is scheduled to close in 2027.

STAR WITNESS

Weisselberg was the star government witness against his employer.

He told jurors that Trump signed bonus and tuition checks, and other documents at the heart of prosecutors’ case, but was not in on the tax fraud scheme.

Though no longer CFO, Weisselberg remains on paid leave from the Trump Organization. He testified in November that he hoped to get a $500,000 bonus this month.

Weisselberg testified that the company is paying his lawyers. It is paying Rothfeld as well, a person familiar with the matter said. Rothfeld declined to comment.

Trump was not charged and has denied wrongdoing. The Manhattan District Attorney’s office is still investigating his business practices.

Merchan will also sentence the Trump Organization on Friday. Penalties are limited to $1.6 million.

Weisselberg remains a defendant in New York Attorney General Letitia James’ $250 million civil lawsuit alleging that Trump and his company inflated asset values and Trump’s net worth.

Rothfeld said he advised Weisselberg not to go outside at Rikers because of the risk of violence in courtyards, and not to interject himself into conversations between other inmates.

“The goal is to keep to yourself,” Rothfeld said.

Reporting by Karen Freifeld; Editing by Richard Chang

Our Standards: The Thomson Reuters Trust Principles.

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Trumps had role in fraud scheme, Allen Weisselberg testifies at company’s trial

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Former Trump Organization chief financial officer Allen Weisselberg testified in court Thursday, describing how Donald Trump and two of his children allegedly participated in a scheme to defraud tax authorities.

Weisselberg said Donald Trump, or at times Eric Trump or Donald Trump Jr., signed checks to pay up to $100,000 for private school tuition for Weisselberg’s grandchildren. Weisselberg said he then instructed the company’s controller to deduct the $100,000 from his salary, allowing him to report a smaller income. Copies of some of the checks signed by the Trumps have been shown in court. 

Weisselberg said the first time Trump signed a tuition check, Weisselberg told him, “Don’t forget, I’m going to pay you back for this.” The payback, he said, was the salary reduction.

Two Trump Organization entities and Weisselberg are accused of more than a dozen counts of fraud and tax evasion. Weisselberg entered a guilty plea in August, admitting to charges filed by the Manhattan District Attorney’s Office accusing him of receiving more than $1.7 million in untaxed compensation.

Weisselberg, who is still on the Trump Organization’s payroll, has over the first two days of testimony described a litany of benefits he and several other executives received for which he said their salaries were similarly reduced to avoid paying taxes.

He said for himself and several other executives, the salary reductions were then mitigated by hefty bonus checks paid to the executives as if they were independent contractors for Trump Organization entities.

“Donald Trump always wanted to sign the bonus checks” before he became president in 2017, Weisselberg said.

That practice ceased during the next two years after an internal review led to changes at the company, he said.

“We were going through a company-wide cleanup process, making sure that since Mr. Trump was now president, everything was being done properly,” Weisselberg said.

Former Trump Organization chief financial officer Allen Weisselberg testifies at the company’s trial on fraud charges in New York.

Jane Rosenberg


Weisselberg said the funds delivered as independent contractor payments were used to set up Keogh retirement plans, tax-deferred pension accounts designed for people who are self-employed.

Defense attorneys for the Trump Organization have said the company did nothing wrong, and laid the scheme squarely at Weisselberg’s feet, saying he hid the salary reductions and independent contractor payments from the Trumps. 

Trump Organization attorney Alan Futerfas asked Weisselberg Thursday, “What human being did you scheme with?”

Weisselberg replied, “Jeff McConney,” referring to the company’s controller, who previously testified during the trial. McConney was granted immunity in exchange for grand jury testimony in the case, and blamed Weisselberg for the scheme.

Futerfas continued with questions seeking to differentiate the Trumps from the executives who worked beneath them.

“Did you conspire with any member of the Trump family?” Futerfas asked.

“No,” Weisselberg replied.

“Did you scheme with Jeff McConney?” Futerfas asked.

“Yes,” Weisselberg replied.

“Did you scheme with any member of the Trump family?” Futerfas asked.

“No,” Weisselberg replied.

Later, Futerfas asked, “Aside from family members, you were among the most trusted people they knew. Is that correct?”

“Correct,” Weisselberg replied.

Soon after, Futerfas asked, “Are you embarrassed about what you did?”

Choking up, Weisselberg replied, “More than you can imagine.”

Earlier Thursday, Weisselberg said under questioning by a prosecutor that other executives at the company were active participants in, and beneficiaries of, similar salary and bonus arrangements.

Weisselberg described arranging for his son Barry’s family to live in a newly-renovated apartment on New York’s tony Central Park South. He said the location was convenient for Barry Weisselberg’s job as manager of an ice rink and carousel run by the Trump Organization in Central Park. Allen Weisselberg said his son paid $500 out of pocket and $500 from his salary per month to rent the apartment, which he described as a “below market” rate.

At the time, Allen Weisselberg and his wife lived in an $8,200 per month company-owned apartment under a lease agreement signed by Donald Trump himself.

Allen Weisselberg said he provided his son’s tax paperwork for preparation to the outside accountant who was in charge of the entire Trump Organization’s annual tax account. Allen Weisselberg said his son’s reported salary at the time “was probably lower than it should have been.”

Peter Stambleck, an attorney for Barry Weisselberg, declined to comment.

Graham Kates

Graham Kates is an investigative reporter covering criminal justice, privacy issues and information security for CBS News Digital. Contact Graham at KatesG@cbsnews.com or grahamkates@protonmail.com

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Trump CFO Allen Weisselberg pleads guilty in tax-fraud case

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NEW YORK — Allen Weisselberg, the longtime top financial officer of former president Donald Trump’s company, pleaded guilty on Thursday to committing more than a dozen felonies, including criminal tax fraud and grand larceny.

Weisselberg and the Trump Organization were indicted last year by authorities in New York who charged them with concealing certain financial compensation as part of a years-long scheme to avoid paying taxes. The case is part of the churning legal maelstrom still surrounding Trump and his close allies, with local, state and federal authorities scrutinizing everything from his namesake business to his handling of classified government documents since leaving office.

Appearing in a Manhattan courtroom, Weisselberg, 75, acknowledged his part in the scheme outlined by prosecutors — and agreed to testify, if called, at a pending trial for the company. As part of his plea agreement, Weisselberg, Trump’s close and trusted associate for decades, would spend five months in jail, followed by five years of probation.

Chief financial officer of former president Donald Trump’s company Allen Weisselberg appeared Aug. 18 at a N.Y. court, facing more than a dozen felony charges. (Video: AP)

Weisselberg spoke sparingly during the hearing, answering “yes” to affirm his activities and guilt on every count. His future testimony, however, could prove damaging for the former president’s namesake company, which prosecutors say carried out “a sweeping and audacious illegal payments scheme.”

The status of key investigations involving Donald Trump

Weisselberg’s sentence depends on him “testifying truthfully” at the Trump company’s trial, according to the district attorney’s office.

The plea agreement “directly implicates” the Trump Organization in a “wide range of criminal activity,” Manhattan District Attorney Alvin Bragg said in a statement.

“Furthermore, thanks to the incredibly hard work and dedication of the team prosecuting this case, Weisselberg will spend time behind bars,” Bragg said. “We look forward to proving our case in court against the Trump Organization.”

The former president and those close to him have assailed the case, tying it to the thicket of other investigations and scrutiny that he routinely characterizes as a coordinated “witch hunt” by Democrats who dislike him.

In a statement, his company called Weisselberg “a fine and honorable man who, for the past 4 years, has been harassed, persecuted and threatened by law enforcement, particularly the Manhattan District Attorney, in their never ending, politically motivated quest to get President Trump.”

Weisselberg, the company’s statement said, pleaded guilty “in an effort to put this matter behind him and get on with his life.” The company pledged that the two corporate entities charged alongside Weisselberg would not make any plea deal, denying any wrongdoing, and said “we now look forward to having our day in court.”

Jury selection in the Trump Organization’s trial is scheduled to begin in late October, which the company noted was “just days before the midterm elections.”

Word that Weisselberg was expected to reach a plea deal emerged on Monday, his 75th birthday. A person with knowledge of the matter said then that he was not expected to help with an ongoing inquiry into the former president. Weisselberg’s indictment in July 2021 was in part an effort to secure his cooperation against Trump, people with knowledge of the strategy said last year.

“In one of the most difficult decisions of his life, Mr. Weisselberg decided to enter a plea of guilty today to put an end to this case and the years-long legal and personal nightmares it has caused for him and his family,” Nicholas Gravante Jr., an attorney for Weisselberg, said in a statement. “Rather than risk the possibility of 15 years in prison, he has agreed to serve 100 days. We are glad to have this behind him.”

Bragg, who took office earlier this year, has faced public pressure over his office’s investigation into Trump. Two veteran prosecutors involved in the case resigned in protest after learning Bragg would not authorize them to seek an indictment against the former president. Bragg made a public statement in the spring saying the investigation was continuing, and his office reiterated that on Thursday.

“For years, Mr. Weisselberg broke the law to line his own pockets and fund a lavish lifestyle,” New York Attorney General Letitia James (D), who also is investigating Trump and his business practices, said in a statement. “Today, that misconduct ends. Let this guilty plea send a loud and clear message: we will crack down on anyone who steals from the public for personal gain because no one is above the law.”

The former president, who is said to be plotting another bid for the White House, is facing a swell of legal scrutiny, including probes examining efforts to overturn the 2020 election, his handling of classified documents after leaving office, his taxes and his actions related to the Jan. 6, 2021, riot at the U.S. Capitol.

Underscoring the array of probes and legal jeopardy facing the former president and others in his orbit, Weisselberg’s plea came the same day as a hearing in South Florida about whether an affidavit submitted before an FBI search of Trump’s residence might be publicly released.

A day earlier, former New York mayor Rudy Giuliani, who has worked as Trump’s lawyer, appeared before a Georgia grand jury as part of a criminal probe into efforts to overturn the 2020 election. Giuliani has been informed he is a target of that investigation, according to his lawyers.

Trump-allied lawyers pursued voting machine data in multiple states, records reveal

For Weisselberg, who has worked for the Trump family for nearly 50 years, the plea deal signals a seeming endgame to his criminal case that sidesteps a trial in the heart of Manhattan, which would likely have drawn significant media attention.

In the indictment last year, Weisselberg was described as “one of the largest individual beneficiaries” of what prosecutors depicted as a wide-ranging, long-running scheme.

The indictment alleges that the Trump Organization paid the rent and utilities for a Manhattan apartment where he lived, and financed the leases for the Mercedes-Benz cars for Weisselberg and his wife, but failed to report this as income and pay the necessary taxes. The indictment also said he “intentionally omitted” his compensation from his tax returns.

All told, the indictment said, Weisselberg obscured about $1.7 million in his compensation from tax authorities over a period from 2005 through 2017, dodging “hundreds of thousands of dollars in federal, state, and local taxes.”

As part of the plea deal outlined in court, Weisselberg agreed to repay the taxes he owed, along with penalties and interest — a total of $1.9 million, the district attorney’s office said. And if he does not live up to the plea deal, he could face a harsher sentence imposed by the court.

Berman reported from Washington. Shayna Jacobs in New York and Josh Dawsey in Washington contributed to this report.

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Allen Weisselberg, Trump Org’s ex-CFO, set to plead guilty

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NEW YORK (AP) — A top executive at former President Donald Trump’s family business pleaded guilty Thursday to evading taxes in a deal that could potentially make him a star witness against the company at a fall trial.

Trump Organization CFO Allen Weisselberg pleaded guilty to all 15 of the charges he faced in the case. He was accused of dodging taxes on lavish fringe benefits he got from the company, including lease payments for a luxury car, rent for a Manhattan apartment and private school tuition for his grandchildren.

Weisselberg is the only person to face criminal charges so far in the Manhattan district attorney’s long-running investigation of the company’s business practices.

Judge Juan Manuel Merchan agreed to sentence Weisselberg to five months incarceration and five years probation at New York City’s Rikers Island jail complex, although he will be eligible for release much earlier if he behaves well behind bars. The judge said Weisselberg will have to pay nearly $2 million in taxes, penalties and interest.

The plea bargain also requires Weisselberg to testify truthfully as a prosecution witness when the Trump Organization goes on trial in October on related charges. The company is accused of helping Weisselberg and other executives avoid income taxes by failing to accurately report their full compensation to the government.

Trump himself is not charged in the case.

Testimony by Weisselberg could potentially weaken the Trump Organization’s defense. If convicted, the company could face fines or potentially be placed on probation and be forced to change certain business practices.

THIS IS A BREAKING NEWS UPDATE. AP’s earlier story follows below.

NEW YORK (AP) — The chief financial officer of Donald Trump’s company, Allen Weisselberg, will plead guilty to tax violations in a deal that would require him to testify about illicit business practices at the Trump Organization, prosecutors and his lawyer told a court Thursday.

Weisselberg is charged with accepting more than $1.7 million in off-the-books compensation from the former president’s company over several years, including untaxed perks like rent, car payments and school tuition.

Attorney Nicholas Gravante Jr. said his client would plead guilty in exchange for a promised sentence of five months in jail.

Prosecutors said the plea deal would require Weisselberg to admit to each of 15 counts in indictment, to speak in court Thursday about the company’s role in the alleged compensation arrangement and possibly serve as a witness when the Trump Organization goes on trial in October on related criminal charges.

Weisselberg, 75, is expected to receive a sentence of five months in jail, to be served at New York City’s notorious Rikers Island complex, and he will be required to pay about $2 million in restitution, including taxes, penalties and interest, prosecutors told the court. If that punishment holds, Weisselberg would be eligible for release after about 100 days.

Weisselberg is the only person to face criminal charges so far in the Manhattan district attorney’s long-running investigation of the company’s business practices.

Seen as one of Trump’s most loyal business associates, Weisselberg was arrested in July 2021. His lawyers have argued the Democrat-led district attorney’s office was punishing him because he wouldn’t offer information that would damage Trump.

The district attorney has also been investigating whether Trump or his company lied to banks or the government about the value of its properties to obtain loans or reduce tax bills.

Then-District Attorney Cyrus Vance Jr., who started the investigation, last year directed his deputies to present evidence to a grand jury and seek an indictment of Trump, according to former prosecutor Mark Pomerantz, who previously led the probe.

But after Vance left office, his successor, Alvin Bragg, allowed the grand jury to disband without charges. Both prosecutors are Democrats. Bragg has said the investigation is continuing.

The Trump Organization is not involved in Weisselberg’s expected guilty plea Thursday and is scheduled to be tried in the alleged compensation scheme in October.

Prosecutors alleged that the company gave untaxed fringe benefits to senior executives, including Weisselberg, for 15 years. Weisselberg alone was accused of defrauding the federal government, state and city out of more than $900,000 in unpaid taxes and undeserved tax refunds.

Under state law, punishment for the most serious charge against Weisselberg, grand larceny, could carry a penalty as high as 15 years in prison. But the charge carries no mandatory minimum, and most first-time offenders in tax-related cases never end up behind bars.

The tax fraud charges against the Trump Organization are punishable by a fine of double the amount of unpaid taxes, or $250,000, whichever is larger.

Trump has not been charged in the criminal probe. The Republican has decried the New York investigations as a “political witch hunt” and has said his company’s actions were standard practice in the real estate business and in no way a crime.

Last week, Trump sat for a deposition in New York Attorney General Letitia James’ parallel civil investigation into allegations that Trump’s company misled lenders and tax authorities about asset values. Trump invoked his Fifth Amendment protection against self-incrimination more than 400 times.

___

Follow Michael Sisak on Twitter at twitter.com/mikesisak. Send confidential tips by visiting https://www.ap.org/tips/.



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Allen Weisselberg, a Top Trump Executive, to Plead Guilty in Tax Scheme

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One of Donald J. Trump’s most trusted executives is expected to stand before a judge on Thursday and plead guilty to 15 felonies, admitting that he conspired with Mr. Trump’s company to carry out a scheme to avoid paying taxes on lavish corporate benefits — even while refusing to implicate the former president himself.

As part of the plea deal, the executive, Allen H. Weisselberg, will be required to testify at the company’s trial if prosecutors choose to call on him, and to admit his role in conspiring with Mr. Trump’s company to carry out the tax scheme. That testimony could tilt the scales against the company, the Trump Organization, as it prepares for an October trial related to the same accusations.

Under the terms of the plea deal, Mr. Weisselberg is expected to receive a five-month jail term, and with time credited for good behavior, he is likely to serve about 100 days.

The plea deal does not require Mr. Weisselberg to cooperate with a broader investigation into Mr. Trump, and his admissions will not implicate the former president. His decision to accept jail time underscored the extent of his loyalty to a family he has served for nearly a half-century.

Mr. Weisselberg was indicted alongside Mr. Trump’s family business last year and accused of participating in a scheme in which some employees were compensated with special off-the-books perks. Mr. Weisselberg, prosecutors from the Manhattan district attorney’s office said, avoided paying taxes on $1.76 million of his income over the last 15 years.

In refusing to cooperate against Mr. Trump, Mr. Weisselberg fended off intense pressure from prosecutors fighting for his testimony. They saw Mr. Weisselberg as the ideal cooperator in their wider investigation focused on the former president and his business practices: He entered the Trump orbit in the early 1970s as a junior bookkeeper for Mr. Trump’s father and climbed the ranks at the Trump Organization in the decades that followed, developing an encyclopedic knowledge of its finances.

Despite not securing Mr. Weisselberg’s cooperation, the Manhattan district attorney, Alvin L. Bragg may gain a victory from the deal. His prosecutors now have a potential star witness as they prepare for trial against the Trump Organization. And Mr. Weisselberg, an accountant who served a vital role as the company’s financial gatekeeper, will be branded as a felon.

His plea comes as a number of other investigations swirl around the former president related to his efforts to overturn the 2020 election and his handling of sensitive documents after he left the White House. Last week, F.B.I. agents searched his Florida home, a stunning move that underscores the extent of Mr. Trump’s legal jeopardy.

Mr. Trump is also the subject of a civil investigation being conducted by the New York State attorney general, Letitia James. That inquiry is focused on whether Mr. Trump fraudulently inflated the value of his hotels, golf clubs and other assets to obtain loans.

Last week, Ms. James interviewed Mr. Trump under oath, and the former president invoked his Fifth Amendment right against self-incrimination more than 440 times. Ms. James, whose office also worked on the criminal case against Mr. Weisselberg, will now have to decide whether to file a lawsuit against the former president.

The charges to which Mr. Weisselberg will plead Thursday stemmed from a yearslong criminal investigation conducted by the Manhattan district attorney’s office. Like Ms. James’s civil inquiry, the criminal investigation came to focus on Mr. Trump’s financial statements and the way he represented the value of his assets.

The investigation, which started in 2018, proceeded in fits and starts and was stalled when Mr. Trump fought against the release of his tax returns and other records to the office in a battle that twice reached the U.S. Supreme Court.

While prosecutors were waiting for a final ruling from the court, they began to scrutinize Mr. Weisselberg and the perks he had received from the Trump Organization, including leased Mercedes-Benzes, an apartment on Manhattan’s Upper West Side and private school tuition for his grandchildren.

After they obtained the tax returns, they continued to scrutinize Mr. Weisselberg, hoping to pressure him to cooperate. When they did not receive that cooperation, they indicted Mr. Weisselberg and the company in the tax scheme.

The broader investigation continued, and in December, Mr. Bragg’s predecessor, Cyrus R. Vance Jr., asked prosecutors to begin presenting evidence about Mr. Trump to a grand jury. But Mr. Bragg, who was sworn in on Jan. 1, grew concerned about prosecutors’ ability to show that Mr. Trump had intended to commit a crime, and the presentation was halted.

In February, the two prosecutors who had led the investigation resigned from the office, leaving its future unclear. Mr. Bragg has said that it has continued, but there has been no public indication of its direction in recent months.

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Trump executive Weisselberg expected to reach plea deal

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Allen Weisselberg, the longtime chief financial officer of former president Donald Trump’s company, is expected to reach a plea deal in a criminal case against him, according to two people with knowledge of the matter. Weisselberg was indicted last year on felony charges including tax fraud.

The specific terms of any plea agreement were not immediately clear. One of the people with knowledge of the matter, who spoke Monday on the condition of anonymity, said they expected Weisselberg to be sentenced to about five months behind bars. The person also said Weisselberg is not expected to help with an ongoing inquiry into Trump, who is facing legal scrutiny from multiple directions.

Weisselberg was charged with more than a dozen felony counts when he was indicted last year, among them grand larceny and criminal tax fraud. Before the indictment, a person familiar with the investigation into Trump’s finances had said prosecutors hoped to convince Weisselberg to testify against the former president as part of a deal that would reduce his own legal jeopardy.

The status of key investigations involving Donald Trump

Attorneys for Weisselberg declined to comment on the case’s status Monday, as did the Manhattan District Attorney’s Office. The expected plea deal was first reported by the New York Times. A hearing in the case is scheduled for Thursday.

Weisselberg and the Trump Organization were indicted last year in a case alleging a plot to avoid taxes by concealing executive pay. Prosecutors called it “a sweeping and audacious illegal payments scheme,” while Trump and his attorneys assailed the case as politically motivated. Weisselberg and the company had pleaded not guilty.

News of a potential deal in his case came as ongoing investigations into Trump have continued to dominate headlines. A week earlier, with Trump in New York preparing to be deposed in a civil probe of his business, FBI agents searched his South Florida club for government documents and came away with nearly a dozen sets of classified or top-secret material.

Trump’s secrets: How a records dispute led the FBI to search Mar-a-Lago

The Justice Department’s criminal probe into efforts to overturn the 2020 election is investigating his actions as part of that effort. And in Georgia, prosecutors conducting a criminal probe into efforts to overturn the election have said former New York mayor Rudy Giuliani, who has served as Trump’s lawyer, is a target of that inquiry, his attorney said Monday.

In Manhattan, District Attorney Alvin Bragg has faced pressure over his office’s long-standing investigation into Trump.

Two key prosecutors involved in the case suddenly quit in February, upset they were not approved to seek an indictment against the former president, while a grand jury convened to hear evidence against him was believed to have expired in the spring.

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Allen Weisselberg, Trump Org. ex-CFO, expects more indictments, his lawyer says

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“We have strong reason to believe there could be other indictments coming,” Bryan Skarlatos said at a pre-trial hearing in New York State Supreme Court.

Weisselberg faces 15 state counts, including grand larceny, which were unveiled by Manhattan District Attorney Cy Vance in July. The grand jury indictment alleged a 15-year tax evasion scheme in which Weisselberg received from the Trump Organization an array of luxury perks — including an Upper West Side apartment, a pair of Mercedes-Benz cars for him and his wife, and private school tuition for two family members — in lieu of compensation.

The former president’s namesake business was also charged in the indictment, but Donald Trump himself has not been charged.

The alleged scheme, according to prosecutors, allowed Weisselberg to evade taxes on $1.76 million in income over a period beginning in 2005. Weisselberg is also accused of concealing his residency in New York City to avoid paying city income taxes.

Weisselberg has pleaded not guilty to the charges.

Monday’s hearing was Weisselberg’s first court appearance in the case since his arraignment this summer.

His lawyer did not identify who else Weisselberg’s team expected to face an indictment in the Vance investigation, but prosecutors have been scrutinizing other top Trump Org. employees, including Matthew Calamari, Sr., the company’s chief operating officer and his son, Trump Org. corporate director of security Matthew Calamari, Jr.

The younger Calamari testified before the grand jury earlier this month and received transactional immunity for the topics he testified about, in accordance with New York state law. The decision to bring him before the grand jury signals prosecutors do not plan to indict him.

Father and son have been under scrutiny by prosecutors over whether they properly paid taxes on subsidized rent and cars they received as benefits from the company, CNN has previously reported.

On Monday, after the hearing, a lawyer for the Calamaris said in a statement that, “We remain in discussions with the District Attorney’s Office relating to” Calamari, Sr. The lawyer, Nick Gravante, said that they “believe there is no basis for indicting” Calamari, Sr.

“If they presently intended to indict him, I would have been informed. I haven’t been and, in fact, have been informed to the contrary,” Gravante said.

At Monday’s short hearing, Skarlatos, an attorney for Weisselberg, referenced a dispute between the Manhattan district attorney’s office and Trump Organization lawyers, saying, he is “concerned” that his client “becomes collateral damage in a bigger fight” between the two.

Holding up a manila envelope with a bulge in it, Skarlatos, said that the parties met in the judge chambers, before the court hearing. “It was represented to us by the [district attorney’s office] that this package includes documents found in a co-conspirator’s basement that are tax documents,” Skarlatos said.

Skarlatos did not identify the co-conspirator by name. CNN has reported that one alleged co-conspirator in the investigation is Jeff McConney, the controller of the Trump Organization. McConney has testified at least twice before the grand jury, in which he received immunity for his testimony.

Solomon Shinerock, a prosecutor with the Manhattan district attorney’s office, responded to Weisselberg’s attorney, saying, “Mr. Weisselberg is the boss. Mr. Weisselberg is also not an innocent party caught up as collateral damage.”

The remainder of the hearing focused on scheduling and an attempt by defense to get longer schedule for motions.

Skarlatos argued that defense attorneys have been handed a large amount of documents by the prosecution, asking the judge judge for an extended schedule for the motions.

Shinerock countered that “Allen Weisselberg is no stranger to these documents.”

The judge agreed to a 120-day motions schedule to begin in January, but noted “many of the documents came from the defendants themselves” and that their claims of needing to go through millions of documents was “a little misleading,” as they are “familiar with most of the documents.”

The next court date was set for July 12, 2022, with trial date not expected until August or early September.

This story has been updated with additional details.

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Takeaways from the Trump Organization and Allen Weisselberg indictment

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It is the first criminal case against former President Donald Trump’s company, one he has derided as a political prosecution.

The crux of the alleged scheme is that the company gave fringe benefits, or perks, to executives including Weisselberg as part of their income, but didn’t pay required payroll taxes on those benefits.

Meanwhile, the recipients of the perks didn’t report them as income and thus didn’t pay income tax on them.

Weisselberg allegedly received a wide array of benefits

On top of his direct compensation from the company, Weisselberg received rent on an Upper West Side apartment, utilities and garage expenses paid for by the Trump Organization, according to the indictment. He and his wife each received a leased Mercedes-Benz. He received nearly $30,000 in cash over a six-year period to pay personal holiday gratuities. He received new beds, flat-screen TVs, carpeting and furniture for his home in Florida.

Trump himself wasn’t charged, but he is referenced

According to the indictment, Weisselberg received perks including $359,058 in tuition payments for Columbia Grammar & Preparatory School for two of his grandchildren. Those payments were made by checks from Donald Trump’s account signed by Trump himself, and later from the Donald J. Trump revocable trust, the indictment said.

The payments for Weisselberg’s grandchildren were “indirect compensation” and were not included on Weisselberg’s W-2 forms, and no income taxes were withheld by the Trump Organization or Trump Payroll Corp. in connection with the tuition payments.

No other individuals were charged Thursday

The Trump Organization, an entity called Trump Payroll Corp. and Weisselberg were charged Thursday — 10 charges brought against the companies and 15 against Weisselberg. But no other individuals have been charged as part of the district attorney’s investigation. The charges do reference an unindicted co-conspirator, which the indictment describes as a person who helped Weisselberg evade taxes.

“From at least 2005 through the date of this indictment, the named defendants and others, including Unindicted Co-conspirator #1, agreed to and implemented a compensation scheme with the object of enabling Weisselberg to underreport his income to federal authorities, and thereby evade taxes and falsely claim federal tax refunds to which he was not entitled,” the indictment says.

A person familiar with the investigation told CNN the unindicted co-conspirator is Jeff McConney, the Trump Organization’s long-time controller.

The investigation isn’t over

The Manhattan district attorney’s office has emphasized that the investigation is ongoing.

The indictment focuses largely on Weisselberg, whose cooperation prosecutors have spent months trying — and failing — to secure. Weisselberg pleaded not guilty Thursday, but if he were to change his mind and decide to assist prosecutors, they could use his testimony and evidence to pursue others.

Additionally, prosecutors have explored a wide range of topics in the course of their more than two years of investigation, and they could add additional charges in the future in what’s known as a superseding indictment.

CNN’s Sonia Moghe and Kara Scannell contributed to this report.

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Trump Organization CFO Allen Weisselberg pleads not guilty to tax charges

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WASHINGTON — The Trump Organization’s chief financial officer, Allen Weisselberg, pleaded not guilty Thursday to tax charges in a Manhattan court after a grand jury indicted him and former President Donald Trump’s company in a case over its business dealings.

Weisselberg, 73, was charged with grand larceny in the 2nd degree, along with other charges and entered a plea of “not guilty.” The Trump Organization also pleaded not guilty.

Prosecutors, in the indictment, described a years-long scheme to compensate executives “off the books” to avoid taxes.

Weisselberg’s attorney, Mary Mulligan, said before the hearing the he “will fight these charges in court.” He was a longtime Trump employee who turned himself in early Thursday morning.

The DA’s office said it does not expect to hold a news conference afterward “as the case relates to an active, ongoing investigation.”

The charges center around a scheme to pay compensation to Weisselberg and possibly others “off the books” by the Trump Organization, NBC News previously reported.

The indictments by the grand jury were obtained by the offices of Cy Vance, the Manhattan DA, and Letitia James, the New York attorney general, two people familiar with the matter told NBC News on Wednesday.

Weisselberg entered the courtroom on Thursday in handcuffs alongside his attorney.

The Manhattan District Attorney moved to secure Weisselberg’s passport as part of the terms of his release. He surrendered his passport to D.A. investigators.

Weisselberg is not necessarily barred from traveling overseas but he has to ask the court’s permission. The judge set a status conference to setup a motion schedule for Sept. 20 at 9:30 a.m.

Vance’s office has been investigating criminal conduct, court documents have shown, such as falsifying business records, insurance fraud and tax fraud at the Trump Organization, which has its headquarters in New York City. NBC News reported in March that Vance was investigating whether Trump employees, including Weisselberg, were able to avoid paying taxes in exchange for fringe benefits, such as apartments.

In a statement Thursday morning, a spokesperson for the Trump Organization said that Weisselberg is “a loving and devoted husband, father and grandfather who has worked at the Trump Organization for 48 years.”

“He is now being used by the Manhattan District Attorney as a pawn in a scorched earth attempt to harm the former President,” the spokesperson said. “The District Attorney is bringing a criminal prosecution involving employee benefits that neither the IRS nor any other District Attorney would ever think of bringing. This is not justice; this is politics.”

Weisselberg’s ex-daughter-in-law, Jennifer Weisselberg, told MSNBC on Wednesday that she’s been in touch with Vance’s office and has turned over documents and has named witnesses. Asked if her former father-in-law is not cooperating with the district attorney’s office because he’s trying to protect his family and the former president, she said, “Not exactly.”

“I think that they’re already in trouble,” she said. “I think that he’s not cooperating. I think when somebody doesn’t cooperate it’s because the other person might just have a lot of leverage on you, and that is a reason why you are afraid to flip.”

Pushed to elaborate, Jennifer Weisselberg said that she thinks the person who has leverage over Allen Weisselberg is “Donald.”

Ron Fischetti, a lawyer for the Trump Organization, said last week that prosecutors were going after the company and its CFO because they “could not get Allen Weisselberg to cooperate and tell them what they wanted to hear and that’s why they are going forward.”

“It looks like they are going to come down with charges against the company and that is completely outrageous. I’ve been practicing for over 50 years and I’ve never seen a case like this where they would indict or charge an individual or a company on tax evasion for using a company car or company apartment and then tie it to the company that he is working for without any evidence that what he did benefited the company,” Fischetti said.

“It’s never been done and it hurts a lot of innocent people who are working at that company, and they are doing this just to get back at Donald Trump,” he said.

Prosecutors are typically hesitant to indict companies because such a move can be a death blow to many innocent employees. The best-known example is that of the auditing firm Arthur Andersen in 2002. Its client was Enron and after that company collapsed in 2001 in an enormous accounting and securities fraud case, Andersen was indicted for obstruction of justice. Prosecutors alleged it had shredded crucial documents having to do with its work for Enron. The indictment of the firm, which had been considered the gold standard for ethics, meant it could no longer gain government contracts.

The firm collapsed after it was found guilty at trial and its 30,000 employees were thrown out of work.

Prosecutors may view the Trump Organization differently, however. It is not a sprawling entity with tens of thousands of employees potentially hurt by an indictment. New York City has already canceled contracts it struck with the Trump Organization to run a city-owned golf course, a move that is in litigation, and an ice skating rink in Central Park. The company does not rely heavily on government contracts that could be lost after an indictment.

The indictment of the Trump Organization, a private company which owns real estate, hotels and golf resorts, comes amid a troubled period for the company hit hard like many by Covid-related shutdowns.

In January, when Trump filed federal financial records of his holdings in his final such disclosure as president, many of the operations showed hemorrhaging revenues. Operations at the Trump National Doral golf resort in Miami were down 43 percent last year from 2019, the records showed, while revenues at Trump International Hotel in Washington’s Old Post Office Building fell by 63 percent, to $15.1 million. Some of his golf courses generated single-digit sales increases, but most of the Trump properties registered declines in revenues last year from 2019.

Tax cases have been brought against New York hotel magnates before.

In 1988, real estate investor Harry Helmsley and his wife, Leona, were convicted of evading $1.2 million in federal taxes. They had billed Helmsley businesses for personal expenses ranging from her underwear to $3 million worth of renovations to their Connecticut estate. At its peak, their real estate empire was worth an estimated $5 billion.

During the Helmsley trial, a former housekeeper testified that she heard Leona Helmsley say: “We don’t pay taxes. Only the little people pay taxes.” Helmsley denied having said it, but the comment stuck.

The indictment was brought by then-Manhattan U.S. Attorney Rudy Giuliani. Then-businessman Trump blamed Leona Helmsley — who’d been dubbed “the queen of mean” — for her husband’s troubles in a letter that was obtained by the New York Post.

“Without the veil of Harry Helmsley, you would be a non-entity. You would not be able to randomly fire and abuse people in order to make yourself happy,” Trump wrote of Leona Helmsley. “What has happened to the legendary Helmsley reputation is indeed sad.”

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