Trump’s Criminal Nightmare Officially Begins

Former President Donald Trump long ago honed his ability to narrowly escape legal consequences into his own personal brand of rare and exceptional performance art.

But like Elvis in his Vegas years, Trump’s act is growing old. Prosecutors are after him like never before—and legal experts, including some who once doubted Trump would ever be charged with a crime, increasingly say the first indictment of a former U.S. president is now a real possibility.  

Just look at Trump’s company. The family business and source of Trump’s ego-boosting fortune, The Trump Organization, was found guilty on Tuesday afternoon by a Manhattan jury of all 17 counts in a corporate tax fraud case. The direct consequences may be no big deal: the company may have to pay a relatively tiny $1.6 million fine when it’s sentenced in January. But the verdict could signal the start of a new season of legal accountability for the former president, since it shows that a jury can be convinced to reach a guilty verdict—17 times in this case—in a matter directly touching Trump. 

That makes it a dark omen for the multiple criminal investigations winding closer to the former president—which carry far more serious potential consequences.  

Trump lost his best tools for staving off prosecutors when he left the White House, including his ability to appoint the Attorney General, and the protection of an internal Department of Justice policy that a sitting president cannot be federally indicted.

“This verdict will embolden federal and state prosecutors to treat him the way he should be treated: like every other citizen,” said Gene Rossi, a former federal prosecutor for the Eastern District of Virginia said. “Trump’s slippery slope is becoming a luge.” 

During the trial, prosecutors slammed Trump’s company as a cesspool of self-dealing, and accused the firm of a 13-year-long scheme of paying employees with off-the-books benefits to avoid taxes. 

“This case is about greed and cheating—cheating on taxes,” prosecutor Susan Hoffinger told the jury.

The Trump Organization’s Chief Financial Officer, Allen Weisselberg, pleaded guilty to receiving $1.76 million in such unreported benefits, including rent on a luxury Manhattan apartment, pricey Mercedes Benzes, parking garage expenses, and tuition at a ritzy private school for his grandchildren. 

Trump’s corporate lawyers argued Weisselberg’s admitted crimes served only Weisselberg, and not the company. But the jury rejected their argument. 

Trump responded with his usual mix of denial and bravado, issuing a statement saying he was “disappointed with the verdict in Manhattan, but will appeal.” Trump has repeatedly denied any wrongdoing, and painted all the investigations as a sprawling witch hunt organized by his political enemies. 

Tuesday’s guilty verdict won’t send anyone to prison, because the case targeted a corporate entity. Weisselberg was charged alongside the company in 2021, but agreed to spend five months in New York’s notorious Rikers Island jail complex in exchange for his guilty plea and testimony at the trial. With good behavior, he may spend only 100 days behind bars. 

Yet the performance of Trump’s legal team in this and other cases should give him little comfort. Trump has struggled to secure top legal talent, and his lawyers have, at times, bungled even basic legal maneuvers. 

This high-profile loss makes Trump look vulnerable, said Carl Tobias, a professor at the University of Richmond School of Law. 

“The major success of convictions on all charges will be difficult to overturn on appeal,” Tobias said. “It may encourage other people and groups who think or suspect that he and his businesses have participated in misbehavior to be more willing to investigate, and even pursue litigation.” 

Tuesday’s guilty verdict was just the latest hit in a drumbeat of terrible legal and political news for Trump.  

On the same day, the House Jan. 6 panel said it plans to make criminal referrals to the Department of Justice, which could include Trump or his top allies. And the man Trump personally picked to run for Senate in Georgia, Heschel Walker, lost to his Democratic rival in one more sign of Trump’s wavering political influence. 

In late November, the DOJ appointed a new special counsel to oversee the department’s two key criminal probes into Trump’s actions at the tail-end of his presidency. Special Counsel Jack Smith will lead investigations into the removal of highly-sensitive government documents taken to Trump’s Mar-a-Lago club in Palm Beach, and also into Trump’s attempts to reverse his defeat in the 2020 election and the Capitol riot of Jan. 6, 2021. 

Smith vowed to move “expeditiously,” and so far, evidence suggests he’s doing just that. On Tuesday, Smith sent grand-jury subpoenas to local officials in Arizona, Michigan and Wisconsin, according to The Washington Post. These states were key to Trump’s effort to remain in the presidency despite losing the 2020 election, and the subpoenas are fresh evidence that Smith means business. 

In Georgia, another aggressive criminal probe also appears to be heading towards a crescendo. 

Fulton County District Attorney Fani Willis is investigating Trump’s attempts to reverse his 2020 electoral defeat. She has empaneled a special purpose grand jury, which has subpoenaed top Trump allies for testimony—including GOP Senator Lindsey Graham, Trump’s former White House Chief of Staff Mark Meadows, his longtime lawyer Rudy Giuliani, former GOP House Speaker Newt Gingrich, former National Security Advisor Michael Flynn, and many others. 

“The allegations are very serious,” Willis told the Post in September. “If indicted and convicted, people are facing prison sentences.” 

Trump may not yet even be done with the Manhattan District Attorney Alvin Bragg, the prosecutor who just successfully branded Trump’s company a criminal enterprise in the Manhattan courtroom on Tuesday.  

One day before the guilty verdict came down, Bragg’s team announced it had hired Matthew Colangelo, a former DOJ official with a history of going after Trump and his company. Bragg has re-upped the Manhattan DA’s focus on an episode that once appeared dormant, according to the New York Times: The hush-money payment to adult film star, Stormy Daniels, who claimed to have an affair with Trump. 

Trump is also grappling with a $250 million civil lawsuit brought by New York Attorney General Letitia James. The case, which was unveiled in September and is now rolling along in court, accuses Trump, his company, and his adult children of lying to banks and insurance providers about the value of Trump’s assets to score financial perks. 

In November, a Manhattan judge granted James’ request to place the company under the supervision of an independent monitor, in a blistering opinion that cited Trump’s company’s “persistent misrepresentations.”

The decision means Trump must notify the judge and James before selling or transferring assets, following a warning from James’ office that the company may have been gearing up to transfer parts of his business empire outside the reach of her lawsuit. 

Tuesday’s decision “will give even more leverage to New York Attorney General Tish James in her civil suit, which seeks extraordinary remedies that would cripple the company,” tweeted Renato Marrioti, a former federal prosecutor. 

The question for Trump now will be whether this loss represents a rare and one-time departure from his longtime ability to thwart prosecutors—or the start of a new trend, in which one defeat leads to another. 

“The leaks in his dam are getting bigger and bigger,” Rossi said.