At present, Donald Trump is facing roughly 982,157 legal issues, a number of which could lead to him doing time in prison. For the past nine months, though, there’s been one legal matter he hasn’t had to worry about: an investigation by the Manhattan district attorney’s office leading to criminal charges. While the DA indicted the Trump Organization and its longtime CFO last year for allegedly running a 15-year tax fraud scheme, and said CFO testified against said company last week, no charges were ever brought against Trump, and an investigation into him personally was effectively shelved last February. But that reprieve is apparently over.

According to The New York Times, Manhattan district attorney Alvin Bragg has refocused its criminal investigation into Trump—but this time, it’s not over the alleged tax fraud that resulted in his company being charged with more than a dozen crimes, or the case Bragg chose to all but drop earlier this year. Instead, the paper of record reports that prosecutors are returning to the matter that originally sparked their investigation into Trump a number of years back: the hush money payment made in the final days of his 2016 campaign to porn star Stormy Daniels, whom Trump sought to silence about an affair she said she’d had with the then candidate in 2006. While the DA’s office, then headed by Cyrus Vance Jr., had ultimately chosen to shift its focus to Trump‘s “broader business practices,” Bragg, as well as some of his deputies, have reportedly “recently indicated to associates, supporters and at least one lawyer involved in the matter that they are newly optimistic about building a case against Mr. Trump” as it relates to the $130,000 payment he made, via his then lawyer Michael Cohen, to Daniels.

Unfortunately, while one might think this would be a slam dunk case given the fact that Cohen, who was reimbursed for the payment by Trump, literally went to prison over it, it’s not as clear cut as it looks.

Per the Times:

By the time Mr. Vance obtained Mr. Trump’s tax returns in early 2021, he had developed concerns about indicting Mr. Trump on charges of falsifying Trump Organization records related to the hush money. Falsifying business records can be charged as a misdemeanor in New York. To make it a felony, prosecutors would need to show that Mr. Trump falsified the hush money records to help commit or conceal a second crime.

Mr. Vance’s office examined several secondary crimes Mr. Trump might have been seeking to conceal, people with knowledge of their discussions said, and concluded that the most promising option for an underlying crime was the federal campaign finance violation to which Mr. Cohen had pleaded guilty. But with help from the outside legal experts, the prosecutors ultimately concluded that approach was too risky—a judge might find that falsifying business records could only be a felony if it aided or concealed a New York state crime, not a federal one.

According to legal experts who spoke to the Times, it‘s possible that Bragg “is pursuing a violation of a New York State election law to underpin a potential case,” which Vance briefly considered, ultimately concluding that the payment, made with funds for a federal campaign, was out of the bounds of state law. Though, as the Times notes, it‘s not clear “how Mr. Bragg might resolve that issue.” Also not clear: That their apparent hope of flipping longtime Trump Organization CFO Allen Weisselberg will work this time:

To help build the hush money case, prosecutors are revisiting another strategy that has yet to work: pressuring a top Trump lieutenant, Allen H. Weisselberg, to cooperate. While Mr. Weisselberg has already pleaded guilty to unrelated tax charges and testified last week against Mr. Trump’s company at its trial for the same tax crimes, he has not turned on Mr. Trump. To ramp up the pressure, the prosecutors are considering a new round of charges against Mr. Weisselberg in hopes of securing his cooperation against the former president, the people said. Those potential charges concern insurance fraud and are unrelated to the hush money.

To escalate their pressure campaign on Mr. Weisselberg, prosecutors might threaten him with the insurance fraud charges, according to the people with knowledge of the matter. The possible basis for such a charge was first revealed in a January court filing in the attorney general’s civil investigation and laid out in more detail in the lawsuit her office brought in September. In the lawsuit, she accused Mr. Trump and his company of committing “staggering” fraud by overvaluing its assets by billions of dollars on his financial statements.

Both documents accused Mr. Weisselberg of lying to an insurance underwriter when he claimed that the value of the Trump Organization’s real estate holdings had been assessed by an independent appraiser, when in fact they had not. Because the insurer, Zurich North America, relied on Mr. Weisselberg’s assurances about the valuations to renew its coverage, his misrepresentations could be used as evidence in an insurance fraud case, according to legal experts.

Weisselberg’s lawyer declined the Times’ request for comment. Trump has denied the affair with Stormy Daniels, one counterpoint to that denial being that, unfortunately, she’s been able to go into great detail about the ex-president’s genitalia. It’s also important to note that he did, in fact, authorize the payment to Daniels.

Bess Levin

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