Why New York AG Letitia James is probably Trump's biggest worry right now (not Jack Smith, Fani Willis or Alvin Bragg)

• In two months, Trump faces a civil fraud trial that could run his Trump Organization out of New York.
• Of all his legal perils — indictments included — this one irks him most, Trump biographers believe.

Donald Trump's law-enforcement pursuers have filled our headlines and headspace for so long, they're almost household names.

There's Jack, and Fani, and Alvin, of course, all poised to prosecute the former president criminally.

But there's also Tish — New York Attorney General Letitia James — and though her pursuit of Trump doesn't have a jail cell at the end of its rainbow, she may be the one Trump is most concerned about right now.

If James gets her way at a $250 million civil fraud trial that starts just two months from now, a Manhattan judge will permanently pull The Trump Organization's license to operate as a New York business.

And Donald Trump, Donald Trump, Jr., and Eric Trump would further be banned from ever running a business anywhere in the state. Ivanka Trump has been removed as a defendant in the case.

In other words, the man who introduced himself on the pilot of The Apprentice by crowing,"I'm the largest real estate developer in New York," would be run out of town on a rail, corporately speaking, and his progeny along with him.

The financial and psychic toll to being a mogul in exile would be great, two Trump biographers told Insider.

"I think as a born and raised New Yorker who grew up fantasizing about Manhattan, and truly believed it was the capitol of the world, it will truly damage his sense of self," said author Michael D'Antonio.

"Based on what he's said and done, New York has always been central to who he imagines himself to be," said D'Antonio, who wrote the biography "The Truth About Trump."

"This would be the rare case that he's actually punished in a way that matters."

Why "Tish" may still be his biggest worry

Trump has so far been indicted in Manhattan (District Attorney Alvin Bragg's hush-money document-fraud case) and in Florida (Special Counsel Jack Smith's Mar-a-Lago classified documents case.)

Smith appears on the brink of winning a new indictment, relating to the 2020 election, as does District Attorney Fani Willis in Atlanta.

That would bring Trump's total number of criminal indictments to four, all strenuously denied as "witch hunts" and all carrying potential prison sentences.

But there are many paths to "no jail" for Trump, even if he is convicted.

The paths to "no jail"

Here's an obvious one: a 2024 presidential election win by virtually any Republican candidate, excepting his most strident detractor, former New Jersey governor Chris Christie, would likely result in a federal pardon, which would make Smith's Mar-a-Lago and 2020 election cases go away.

If Democrats keep the White House, that particular prison escape hatch probably closes.

But Trump's federal judges still have great discretion in sentencing.

As long as they publicly explain their reasoning, judges can bypass the statutory sentencing guidelines, which are advisory, not mandatory, and hand out no-jail sentences on a wide range of offenses, including those faced by Trump, explains former federal and Manhattan prosecutor David Aaron.

"The fact that the case is sui generis, and that the defendant is so uniquely positioned, a judge could go in any direction with this — down the middle, or it could be a harder punishment because of an abuse of a high position," said Aaron, now senior counsel at the Manhattan and Washington, DC-based Perkins Coie LLP.

"Or, a judge could say that in this instance, the needs of justice have been served merely by the fact of a prosecution and conviction, and there's nothing greater to be gained by a prison sentence."

Trump happens to have nominated the judge now presiding over the Mar-a-Lago documents case, Aileen Cannon, some of whose pre-indictment rulings have swung wildly in his favor.

Home confinement is one more prison-free option

Several factors that are unique to Trump may make a sentence of home confinement a pragmatic alternative, including the potential for civil unrest should he be imprisoned, and the question of what to do with his ever-present Secret Service contingent, which would accompany him to prison.

Trump would likely have to wear an ankle bracelet, and pay for private security to keep an eye on him, say, on the sprawling, 17-acre grounds of Mar-a-Lago.

But home confinement, while unusual, would not be unheard of, said Ira Judelson, who handled the bail and home confinement for former IMF chief Dominique Strauss-Kahn.

James' law enforcement action against Trump, meanwhile, is civil, not criminal. She can't threaten his physical freedom.

But she is getting first crack at Trump, with a case that's going to trial before any other on his busy docket.

The October 2 trial date is set in stone, warned Manhattan Supreme Court Justice Arthur Engoron, a tough judge that Trump has tried and failed to get removed from the case.

And James is demanding other things of great importance to Trump: money (her lawsuit demands $250 million) the afore-mentioned corporate banishment, and more.

James is alleging Trump committed massive, repeated fraud in a decade's worth of financial statements, as he described the worth of his properties to banks, insurers and tax officials. The phony math, she alleges, let him pocket hundreds of millions of dollars in loans and tax savings.

If she gets the relief that her 200-page lawsuit seeks, the company could simply pick up stakes and move, re-incorporating, say, in Florida or Delaware, but an independent monitor would follow the company across the border, hovering over its financial dealings for five years.

But the toughest penalty, notes D'Antonio, would be James' demand for a five-year ban on Trump, his family or his company acquiring any new real estate in New York — he currently owns Trump Tower, 400 Wall Street, and Trump Park Avenue — and that they abandon Trump Org's New York business address for good.

"As a child growing up in Queens, I think, he was enthralled with Manhattan, as if it were the Emerald City," D'Antonio said.

"He wants to be the cagey and brilliant New York businessman, and I think losing that is going to lead to an injury," he said.

"Nobody imagines the great businessman of Miami. They don't make movies about Bedminster, New Jersey," where Trump has a golf course, D'Antonio added.

"They make movies about Wall Street."

Gwen Blair, author of The Trumps: Three Generations That Built an Empire, agrees that Trump rose to first television, and then political, prominence, through this in-his-own-mind legend of being New York's biggest, savviest and flashiest real-estate mogul.

"He spent the 1980s burnishing that reputation, and going almost a billion dollars in debt scooping up all of the status symbols of being a magnate," she said. "Like a yacht. Like a football team. Like an airline. Like his skyscrapers in Manhattan."

The Apprentice delivered that fantasy directly, and unfiltered, into America's living rooms, with New York City as his co-star, both biographers who spoke to Insider agree.

And if James wins her case this fall, and the judge finds him guilty and grants the relief she seeks, that fantasy will be thoroughly revised in favor of a new fantasy, they also agree.

"The narrative will shift to 'I never liked New York, anyway,' and 'I was doing it a favor, anyway,' and 'I was propping it up — when it was on the ropes I went in and saved it, those ungrateful bastards,'" she predicted with a laugh.

Still, "It's an interesting question, whether that core piece — New York — really matters to him any more," she said.

"I think New York isn't big enough for him any more, even if it was the biggest thing in the universe when he was growing up in Queens," she said.

"Though maybe, in his heart of hearts — and his soul, if he has one — he'll be like a five-year-old boy whose favorite toy got taken away," she said.

"But ever see a nuclear facility? He has cement walls ten-feet deep around that part of him," she said.

He may well lose some sleep, if James chases him out of her state, and he's no longer officially a New York real-estate mogul, Blair added.

"But if he wakes up at three o'clock in the morning, he'll just have a chocolate shake. Maybe a cheeseburger. And go back to sleep."

This story was updated to reflect that Ivanka Trump was removed as a defendant from the lawsuit.