Will Allen Weisselberg flip on Trump? Executive days away from tax probe charges

Manhattan DA reportedly in final stages of the investigation, could charge Weisselberg to turn up the heat and get him to flip on Trump

                            Will Allen Weisselberg flip on Trump? Executive days away from tax probe charges
Allen Weisselberg's name has cropped up in connection with financial fraud investigation against DonaldTrump and his company (The Trump Organization; Tasos Katopodis/Getty Images)

The Manhattan District Attorney is reportedly in the final stages of its criminal tax investigation into the Trump Organization. It is likely that top executive Allen Weisselberg could be criminally charged in the coming days. Prosecutors are hoping that the charges will turn up the heat enough for Weisselberg to flip on Trump, but the big question is will he?

Weisselberg, the Chief Financial Officer of the Trump Organization is reportedly a close confidant of the ex-President. He has been at the center of Manhattan DA Cyrus Vance's extensive probe into the Trump Organization, which in May convened a grand jury to hear the case. The case is also famously centered on Trump's tax returns, which Trump was forced to hand over after legal challenges for over a year. 


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The exhaustive investigation is just one of the several into Trump but is currently the most advanced. Charges are expected in the coming days, with the DA having a full picture of Weisselberg and his finances. For months, Vance has been attempting to get Weisselberg to flip on Trump, but to no avail. Can he do so with criminal charges? To understand that, we first need to look into the case against the executive.

The case against Weisselberg

The DA began looking to Weisselberg after it emerged that the Trump Organization was providing "fringe benefits" to its top executives. Those benefits are taxable, but it appears as if tax wasn't paid by Weisselberg and others. There are some exceptions, and the rules aren't always clear, but usually, some benefits are taxable. In the case of Weisselberg, the DA found that the Trump Organization provided him with apartments, leased cars, and even private school tuition fees for his grandchildren. 

By obtaining and examining Weisselberg's tax returns, the DA found that Weisselberg has been receiving these taxable benefits from the company. The investigations led to prosecutors subpoenaing records from the Columbia Grammar and Preparatory School, where Weisselberg's grandchildren are reportedly studying. Along with that, the DA has also managed to get his former daughter-in-law, Jennifer, to cooperate with the investigation. 

Jennifer is being probed about the benefits her former husband Barry Weisselberg received, including an apartment on Central Park South and Mercedes-Benz cars. Together, all this information has helped the DA build a solid case against Weisselberg. The New York Times, which broke the story, noted that the full scope of the investigation could not be determined. "It is rare for prosecutors to build a criminal case solely around a failure to pay taxes on fringe benefits," they said. 

Will Weisselberg flip on Trump?

Experts The Times spoke to say Weisselberg could be facing charges for grand larceny, scheme to defraud, or tax fraud. All those charges come with steep repercussions. Failure to pay more than $10,000 in taxes in a single year can be punishable by up to seven years in prison. Scheming to defraud has a maximum of four years. Of course, getting a conviction won't be that easy. The Times noted that "Mr. Weisselberg’s lawyers could argue that some of the benefits were not taxable, or that Mr. Weisselberg did not know he needed to pay taxes on them," because the rules are so opaque.

But, even if Vance manages to secure charges, it is being considered as a big win. Reportedly, charges indicate that "prosecutors have identified what they believe is misconduct," at the Trump Organization. But that could leave employees like Weisselberg on the hook, not necessarily Trump. If Vance wants to charge Trump, he will need Weisselberg's cooperation. For decades, Weisselberg has been Trump's financial gatekeeper and a very close ally, indicating he knows a lot about the former President. 

So far, he has refused to flip and is still working at the Trump Organization. But with changes coming, there is a possibility that could change. We know the DA has his and Trump's tax returns, records from several banks that worked with the company, Jennifer's testimony, and Trump's former fixer Michael Cohen is also reportedly cooperating with investigators. Reportedly, Weisselberg's aide Jeffrey McConney has already testified in front of the grand jury, but he is not expected to flip. 

Together, these facts indicate that Vance has a strong case, but just how strong is a matter of debate. We won't know until the charges are made public, and we know the full scope of the investigation into the company. Trump though seems unworried. Both Weisselberg and McConney are known to be immensely loyal to Trump, indicating that the former President has little to fear. 

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