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NEW YORK - If Donald Trump was looking for some good news on his 75th birthday last Monday, it arrived at 8:15 a.m. by way of a blue Mercedes slipping into Trump Tower's private garage entrance on West 56th Street.
Behind the wheel was Allen Weisselberg, Trump's longtime confidant and Trump Organization chief financial officer, whom the Manhattan District Attorney's Office has pressed to turn on the former president as they investigate Trump's business dealings.
Every day that Weisselberg arrives for work at Trump Tower - as he did that day, steering in from his Upper West Side apartment across town - could be seen as a public signal that he is sticking with Trump and deflecting investigators' advances.
As the most senior non-Trump executive at the former president's private, closely held company, Weisselberg is probably a key figure in prosecutors' efforts to indict Trump, legal experts say. His central role in nearly every aspect of Trump's business, revealed in depositions and news interviews over the past three decades, afforded him what former employees say is a singular view of the Trump Organization's tax liabilities and finances.
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Although that role long allowed him to stay behind the scenes, it may place him front and center in what would be an unprecedented prosecution of a former president, should the investigation advance.
More than two years after opening an inquiry of the Trump Organization, Manhattan District Attorney Cyrus R. Vance Jr. has convened the grand jury that is expected to decide whether to indict the former president, according to two people familiar with the development, and is pressing Weisselberg to provide evidence implicating Trump.
Yet officials involved in the Weisselberg investigation have grown frustrated about what they view as a lack of cooperation from Weisselberg and believe he continues to regularly speak with Trump, according to a person familiar with the inquiry.
As the investigation proceeds, Trump has returned to New York on several Sunday evenings from his golf club in New Jersey, where he typically spends the summer. On Trump's birthday, hours after the former president had arrived at the building where he has a home and office, Weisselberg left his apartment and arrived at Trump Tower about 40 minutes later.
Early Tuesday, Weisselberg, wearing a suit and carrying a briefcase, again came out of his apartment building, but pivoted back inside when he saw a reporter outside.
Former Trump employees have described Weisselberg as having been entrusted with nearly every aspect of Trump's business, a figure who signed most of the company's checks and monitored expenses as small as pens.
"Just to say 'He's the money man' actually underestimates his role. He was more than that even. He was the whole enchilada," said Tristan Snell, who headed the New York attorney general's investigation of Trump University, which led in 2016 to a $25 million settlement of fraud allegations. "Allen Weisselberg really ran the whole company."
Trump and Weisselberg have worked together through numerous legal battles before now, with both of them having to repeatedly provide testimony to plaintiffs' attorneys and prosecutors in earlier cases.
Weisselberg handled the finances for Trump's charitable foundation, which admitted to self-dealing and dissolved in 2018 after coming under investigation by the New York attorney general, according to a deposition he gave in 2017. He oversaw spending decisions at Trump University, the online program that drew three lawsuits before the settlement, according to his deposition in one of those cases. He signed checks to former Trump lawyer Michael Cohen that Cohen says were reimbursements for illegal payments Cohen made to Stormy Daniels and Karen McDougal to prevent them from publicly alleging they had affairs with Trump. (He received immunity in a federal case against Cohen. Cohen later pleaded guilty to eight criminal counts and received a three-year sentence.)
But neither Trump nor Weisselberg was charged with crimes in any of those cases. Investigators for Vance, D, and New York Attorney General Letitia James, D, now working together, have considered a range of possible corporate and personal fraud charges, according to people familiar with the investigation and public court filings.
At the nexus of Weisselberg's role in the Trump operation and investigators' publicly known interests are the former president's business and personal taxes. Weisselberg has handled Trump's corporate finances, which are closely intertwined with Trump's personal wealth, for more than three decades.
Investigators have subpoenaed tax, banking and insurance records from Trump's company and business partners. They have also scrutinized compensation provided to Weisselberg's son, Barry, while he was working as an ice rink operator for the company, information turned over by Barry Weisselberg's ex-wife under a grand jury subpoena. Investigators could seek to use any legal vulnerability involving Barry Weisselberg to pressure his father into turning against the former president, according to legal experts.
Authorities have not accused Trump or either Weisselberg of wrongdoing, and it remains possible that the investigation will end without anyone being criminally charged. Allen Weisselberg's attorney, Mary Mulligan, declined to comment, and he avoided a reporter outside his home Monday and Tuesday last week. A lawyer for Barry Weisselberg did not respond to a request for comment. Spokespeople for Trump and the Trump Organization did not respond to questions. Trump has called the investigations politically motivated "witch hunts."
Spokespeople for Vance and James declined to comment.
Weisselberg will turn 74 in August. If authorities move against him, as some legal experts predict, he may have to decide whether to face charges, possibly alongside his son, or to accept a deal that would require testifying against Trump, who avoids using email - creating little documentation of his decision-making.
Without Weisselberg's cooperation, legal experts say, it's unclear whether prosecutors would be able to establish any required intent on Trump's part were they to allege that the Trump Organization or any of its officers committed crimes. (The district attorney has the option to indict companies rather than individuals.)
Those experts say Weisselberg's legal exposure could be significant - including the possibility of prison time - if the district attorney is able to prove allegations that have been reported, such as misrepresenting the company's assets or income with banks, insurers or tax authorities.
"I think he's playing Russian roulette with the district attorney's office if he thinks that even if he is indicted he is going to get a pass," said Robert C. Gottlieb, a New York defense lawyer and former prosecutor for the district attorney. "We're not talking about fraud involving a few thousand dollars, we're talking about allegations of a massive fraud involving millions of dollars over an extended period of time in which he was CFO."
Weisselberg has long been considered Trump's most trusted nonfamily lieutenant and his role at the company appears only to have increased since Trump entered the White House. Recent Trump Organization public filings, in fact, show Weisselberg playing a more active role at some Trump businesses than Trump himself.
Since Trump left office, for example, the company has not changed the official management structure at the Trump hotel near the White House, according to the General Services Administration, the agency that holds the lease on the building. Under that structure, set up to distance Trump from his businesses while he was in the White House, Trump still owns a majority stake in the hotel, through a trust managed by Weisselberg and Trump's two adult sons. But the former president does not play a role in its management.
In Florida this year, the Trump Organization filed annual reports for 40 subsidiaries operating in the state. Weisselberg was listed as an officer of all 40, usually along with one or both of Trump's adult sons. Trump was largely absent, having not retaken the leadership roles he held before he became president. He was listed as an officer of just one company: He is the president of the Mar-a-Lago Club in Palm Beach, a designation that allowed him to reside at the for-profit club after neighbors raised objections.
"At such a small company, he was the kind of person who you wanted to know you," said one former employee, speaking about Weisselberg on the condition of anonymity to share details about the company. "He was in charge of everything."
Snell said that Weisselberg exercised tight control over all of the organization's subsidiaries while Trump focused on marketing, licensing and his TV career on NBC's "The Apprentice," the show that vaulted him to national fame.
In interviews and depositions for prior cases, Weisselberg has described his relationship with Trump as close but one-sided.
"I wouldn't go in there and just chitchat," he said in a 2015 deposition, of his visits to Trump's office. "But if I had a reason to go in and discuss a business matter or needed a decision or some idea or concept, we'd have a conversation."
In a 2017 deposition about the foundation, Weisselberg said that he had been surprised one day in 2016 when Trump asked him to come to Iowa to attend a campaign rally in Des Moines.
"I had never gone anywhere with Donald on any kind of - anything," Weisselberg said, describing his surprise at the invitation. "It doesn't matter what I thought. He's my boss. So I went."
In a 2015 deposition, Weisselberg said he earned $450,000 per year, with bonuses from $200,000 to $400,000. "I take no vacations . . . I work a lot, and pretty much I - I'm in work all the time," he said, according to a nonpublic transcript obtained by the New York Daily News.
Public accounts of depositions show that Weisselberg had an unusually detailed view of the Trump Organization's spending, insisting on signing the company's checks himself.
"I felt by signing checks, which I do for all of our entities, I get a good feel for what the company is doing on a day-to-day basis, as opposed to waiting to get reports months after the fact," Weisselberg said in the 2015 deposition, taken as part of a lawsuit against Trump University. He said he focused on all manner of expenditures, including individual employees' bonuses, and the prices that Trump subsidiaries were paying for office supplies.
In one deposition, he recalled from memory detailed financial figures from across the company: 300 memberships for sale at Trump's golf course in Bedminster, N.J.; 55 home lots the company intended to sell at Trump's course in Los Angeles; and the $10.4 million cost of the clubhouse at Trump's golf club in West Palm Beach.
But in other instances, Weisselberg - when asked about apparent discrepancies in Trump's claims or an incident of alleged misconduct - has cited a lack of knowledge or a lapse in memory.
"I wish I could answer," he told investigators for the New York attorney general's office in 2017, as he was pressed about an improper $25,000 political gift made by the foundation. Investigators wanted to know how the gift had been hidden in the charity's tax returns, replaced with a nonexistent gift to another group. Weisselberg said it must have been a series of mistakes he called "the perfect storm." But he could not say who exactly made them.
The New York attorney general's office has disclosed in public filings that it has investigated whether the Trump Organization manipulated the valuation of four of its properties by potentially inflating the values for banks or insurance companies, but minimizing them for tax purposes.
Investigators also said they had questioned Weisselberg about whether the Trump Organization paid income taxes after a lender forgave more than $100 million of its loans in 2012. Trump Organization lawyers had said Weisselberg could confirm that the proper taxes were paid, James' office said.
But when questioned, he could not. "Mr. Weisselberg testified that . . . he had no firsthand knowledge of this fact, had not reviewed the relevant documents to confirm that this 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 with the Trump Organization's accountants concerning the tax treatment of the amount of the debt that was forgiven," James's office wrote in a filing in August.
Weisselberg's apparent unwillingness to assist the investigation at what appears to be a mature stage may narrow his options down the road were he to be indicted, according to legal experts.
New York criminal defense and civil rights lawyer Earl S. Ward said that wealthy, white-collar defendants in Manhattan state court often walk away with "a wrist-slap compared to individuals who are poor and commit economic crimes of desperation."
That's not likely to be the case for Weisselberg "only because of the real target in this investigation," he said, referring to Trump. Ward has handled a number of cases in the New York Supreme Court, where a criminal indictment of Trump would be heard.
"Typically in state court in New York County if you're charged with a financial crime and you're a rich millionaire you're not going to go to jail - it rarely happens," Ward said. "The difference here is that there's a real target in this investigation and given who that target is, I'd be surprised if [Weisselberg] gets off scot free."
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The Washington Post's Kevin Armstrong contributed to this report.
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