‘Very real chance’ Donald Trump will go to jail amid escalating legal woes

Nearly three months after leaving the White House, Donald Trump is facing a “very real chance” his escalating legal woes will send him to prison.

Two-and-a-half months after leaving the White House, Donald Trump is, among other things, reportedly plotting a 2024 reprisal of his role as leader of the free world, from the comfort of his eponymous Mar-a-Lago resort in Florida’s Palm Beach.

But if the former president’s escalating legal woes are anything to go by, there’s a “very real chance” he won’t be heading back to the White House, but to prison instead.

In addition to being the defendant in no fewer than 29 lawsuits, according to The Washington Post, the 74-year-old is also the subject of multiple criminal investigations — including one in which lawyers had obtained access to his tax returns, after a four year fight on Mr Trump’s part to keep them secret.

Trump denies any wrongdoing, having previously said he’s “proud” of his tax returns, and labelling the attempts to force him to show them a “political prosecution”.

The investigation into whether, along with the Trump Organisation, he has committed bank, tax and insurance fraud has stepped up a notch in recent weeks, when the personal bank records of Allen Weisselberg, the self-described “eyes and ears … from an economic standpoint” of Mr Trump were subpoenaed.

“Mr Weisselberg, who has not been accused of wrongdoing, has overseen the Trump Organisation’s finances for decades and may hold the key to any possible criminal case in New York against the former president and his family business,” reporters for The New York Times wrote on Wednesday.

People with knowledge of the matter also told The Times that prosecutors are seeking a new round of internal Trump Organisation documents, to then “compare those details (of each Trump property’s financial situation) against the information the company provided to its lenders and local tax authorities to assess whether it fraudulently misled them”.

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There’s a “very real chance” Donald Trump could go to prison. Picture: Olivier Douliery/AFP

Michael Cohen, the former personal lawyer for Mr Trump, leaves the Manhattan District Attorney’s Office after meeting with prosecutors. Picture: Michael M Santiago/Getty Images/AFP

While Mr Trump likely won’t go to jail for “the rest of his life”, it’s “pretty likely” that, if proven guilty of insurance and bank fraud, it could “lead to criminal charges and that would carry jail time”, The Daily Beast legal analyst Jay Michaelson said in late February.

“If Trump did commit crimes of some sort, even if they’re kind of, you know, sort of ordinary business crimes — if he died, it’s important that there not be a culture of impunity in this country, that there needs to be a message sent that there are consequences, no matter how rich and important you are, if you break the law,” chief Washington correspondent for The New Yorker, Jane Mayer, told NPR’s Terry Gross.

But, Mayer added, people she’d spoken to who know Trump are sceptical that he’ll ever serve time in prison, predicting instead that “he would flee”.

“It’s hard to know what to expect. But it’s — for me, anyway, it’s hard for me to contemplate him truly in an orange jumpsuit at, you know, Rikers Island,” she said.

“I think there’s absolutely a chance that he could face serious charges and be convicted. I mean, this is no joke.”

In addition to the criminal probe, Mr Trump was also sued this week by two Capitol Police officers, who battled the angry mob that the self-described billionaire was accused of “inciting” on the US Capitol back in January.

Officers James Blassingame and Sidney Hemby are demanding damages for the physical and emotional injuries they suffered during the violent insurrection — that killed five people — in a federal lawsuit.

“The insurrectionist mob, which Trump had inflamed, encouraged, incited, directed, and aided and abetted, forced its way over and past the plaintiffs and their fellow officers, pursuing and attacking them inside and outside the United States Capitol, and causing the injuries,” the suit states, according to The Washington Post.

“Officer Hemby was attacked relentlessly. He was bleeding from a cut located less than an inch from his eye. He had cuts and abrasions on his face and hands and his body was pinned against a large metal door, fending off attacks.”

Officer Blassingame, who is Black, faced “endless threats and attacks” from the mob, and “it was not clear to him on January 6 that he would survive to make it home”.

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Mr Trump was also sued this week by two Capitol Police officers, who battled the angry mob that he was accused of “inciting” on the US Capitol. Picture: Roberto Schmidt/AFP

Mr Trump also faces multiple defamation suits — including writer E. Jean Carroll’s, who accused him of sexually assaulting her in Bergdorf Goodman in late 1995 or early 1996, only for him to deny her allegations and accuse of her lying to drum up sales for a book.

Another, involving former Apprentice contestant Summer Zervos, has been given the green light to move forward after Mr Trump’s lawyers attempted to get it dismissed because he was the president.

Ms Zervos came forward in the lead-up to the 2016 election, alleging that Mr Trump groped and kissed her without her consent in 2007. In 2017, she sued him for defamation after he denied her allegations and called her story a “hoax”.

“Now a private citizen, the defendant has no further excuse to delay justice for Ms Zervos, and we are eager to back to the trial court and prove her claims,” a lawyer for Ms Zervos, Beth Wilkinson, told The Wall Street Journal in a statement.

Originally published as ‘Very real chance’ Donald Trump will go to jail amid escalating legal woes