Trump Organization Chief Financial Officer Allen Weisselberg was led through a courthouse in handcuffs on Thursday. Some are salivating at the prospect of former President Donald Trump meeting the same fate.
“Donald Trump’s odds of going to prison just skyrocketed,” was the headline on Vanity Fair. Former Trump attorney and fixer Michael Cohen predicted “sleepless nights for the Trump family, Weisselberg, [Trump Organization chief operating officer Matthew] Calamari, and others.”
“The media is already f***ing up the narrative as usual, so let’s be clear: there is no way the Manhattan DA would be indicting the Trump Organization unless it’s a precursor to indicting Donald Trump and other Trump family members,” tweeted a popular Resistance account as the indictment was first reported. “Today’s news means Trump is going to prison.”
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Outside fervent anti-Trump circles, there were more measured predictions that the investigation into unpaid taxes would derail any attempted comeback by the former president, possibly ending his political career.
New York Times reporter Maggie Haberman told CNN that Trump is “dealing with the reality of a trial in, say, 18 months. … It’s hard to see somebody running for president with a trial playing out about how their company did business.”
Trump was elected in 2016 despite being a political neophyte, in no small part because of his reputation for business acumen. “George, it’s called management,” he told ABC News’s George Stephanopoulos in a 2015 interview when asked how he would accomplish his immigration policy objectives.
Yet, Trump has survived many past predictions of legal jeopardy and political demise, from the release of the lewd Access Hollywood tape, special counsel Robert Mueller’s Russia investigation, the controversy over payments to Stormy Daniels, two impeachment trials, and various past looks into his charitable foundations and business dealings.
“The political Witch Hunt by the Radical Left Democrats, with New York now taking over the assignment, continues,” Trump shot back in a statement on Thursday, connecting the Trump Organization charges to past investigations he has described in similar terms. “It is dividing our Country like never before!”
Liberals, and some Never Trump conservatives, have speculated about the former president, Ivanka Trump, and Jared Kushner being incarcerated. Others talked about the military removing Trump from office following last year’s presidential election.
Trump’s highly publicized trip to the border this week alongside Texas Gov. Greg Abbott and regular post-presidential appearances on the front page, for reasons other than his business’s legal woes, show that he remains a political force. Republicans still fete him, and supporters turn out for his campaign-style rallies.
“If Jan. 6 didn’t move the party away from him, I don’t see why this will,” said a Republican strategist.
The charges against Weisselberg coincide with a Democratic-led House investigation into the Jan. 6 Capitol riot, waged by Trump supporters who wanted to disrupt the electoral vote certification based on his allegation of voter fraud.
Weisselberg stands accused of failing to pay taxes on a variety of company perks. Trump foes hope the charges will be a precursor to Weisselberg flipping against the former president, implicating him in criminal activity. Assistant Attorney Carey Dunne described the tax fraud the Trump Organization CFO is alleged to have engaged in as “orchestrated by the most senior executives.”
The investigation is said to extend beyond Weisselberg into whether the Trump Organization “overvalued and undervalued its assets on loan, tax, and insurance documents for financial gain,” according to the Wall Street Journal.
The Trump Organization said in a statement that Weisselberg was “being used by the Manhattan District Attorney as a pawn in a scorched earth attempt to harm the former President.”
Trump himself believes that Manhattan District Attorney Cyrus Vance Jr. and fellow Democrat New York Attorney General Letitia James are engaged in a partisan vendetta. He has described them as “Radical Left” prosecutors who are “rude, nasty, and totally biased.”
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If Trump weathers the latest legal storm, he could try to become the first president to serve nonconsecutive terms since Grover Cleveland. His contemplation of a third straight presidential campaign is casting a shadow over the 2024 Republican White House field, though any further developments in the Trump Organization investigation could change that.
Trump reportedly believes that voters will see the investigation as politically motivated and that it will work against President Joe Biden in a rematch.

