Trump's legal troubles come to a head in New York

When Donald Trump campaigned for president back in 2016, he defended his lifelong hometown with the kind of vigor one might expect from a blunt-talking New Yorker, telling then-rival Sen. Ted Cruz, "When you want to knock New York, you've got to go through me."

But lately, New York has been knocking back. Trump's relationship with the Big Apple took an adversarial turn during his presidency, and recently a series of court actions have summoned him back from his new home state of Florida.

The cases have drawn out for years, both civil and criminal, state and federal, and "it's not a total coincidence that it's all coming together at once," according to former federal prosecutor E. Danya Perry.

"He very successfully and deftly managed to put so much of it on ice while he was president," said Perry, a defense attorney who also previously served as a New York State deputy attorney general.

E. Jean Carroll defamation case and forthcoming sexual assault lawsuit

At the federal court on Pearl Street in lower Manhattan, a judge last week ordered Trump to sit Wednesday for his second high-stakes deposition in three months. He'll be questioned by a lawyer for author E. Jean Carroll, who sued Trump for defamation in 2019 after Trump accused Carroll of lying when she said he raped her in the mid-1990s.

Judge Lewis Kaplan wrote that Trump's deposition may be used in another civil suit Carroll has pledged to file, a sexual assault claim against Trump.

Carroll will be able to pursue the lawsuit next month when a new state law, the Adult Survivors Act, briefly removes the statute of limitations for such claims in New York.

Trump has repeatedly denied Carroll's allegations.

Civil fraud lawsuit against Trump and his company

A block east of the federal courthouse is the Centre Street state civil court where for years attorneys for Trump and his company fought a losing battle to limit subpoenas in a sprawling New York attorney general probe into their financial practices. Trump's other recent deposition was ordered by Judge Arthur Engoron in this case.

Trump invoked the Fifth Amendment more than 400 times during the August questioning. His deposition was among the last pieces of evidence collected before the New York Attorney General filed on Sept. 21 a sprawling lawsuit that aims to kneecap Trump's company. New York is seeking $250 million in damages and an end to Trump business in the state. In addition to the Trump Organization, the attorney general's suit names Trump and three of his children — Don Jr., Ivanka and Eric Trump — as defendants.

The company and the Trumps have denied all allegations in the case and said through an attorney in September that "absolutely no wrongdoing has taken place." They have previously accused New York Attorney General Letitia James in public and in court filings of pursuing the investigation out of political animus.

The complaint alleges the Trumps and other executives at the company engaged in a yearslong scheme to enrich themselves by inflating the values of properties across the country.

That investigation was prompted by congressional testimony given in 2019 by former Trump attorney Michael Cohen, who said at the time that "Trump inflated his total assets when it served his purposes … .and deflated his assets to reduce his real estate taxes."

Cohen told CBS News that he believes Trump "has broken the law," but that the alleged fraud may never have been exposed had Trump not run for office.

"He might never had been caught other than the high profile nature of the position and his continuous refusal to adhere to norms," said Cohen, who is now a fierce critic of the former president.

The next hearing in that case is scheduled for Oct. 31.

Manhattan criminal fraud and tax evasion trial

By then, attorneys for the company will be busy one block north on Centre Street, at a state criminal court, where on Monday the Trump Organization's criminal fraud and tax evasion trial will begin.

Among the witnesses expected to be called in that case is former Trump Organization chief financial officer Allen Weisselberg, who in August entered a guilty plea in the case. The judge in that proceeding, Juan Merchan, is also presiding over former Trump adviser Steve Bannon's state criminal fraud case.

At a hearing on Sept. 12, Merchan criticized Trump Organization lawyers for "eleventh hour" changes to their defense team.

"One of the accusations is that the defense is trying to stall. You know, it's starting to feel that way a little bit," Merchan said.

Merchan's rebuke was echoed by Judge Kaplan in the E. Jean Carroll case, who wrote on Oct. 12 that Trump "should not be permitted to run the clock out on (Carroll's) attempt to gain a remedy for what allegedly was a serious wrong."

Trump has long used delay as a court strategy, according to Barbara Res, who was Trump's head of construction in the 1980s.

"His M.O. was to try to do that with contractors when he owed them money and, you know, offer them maybe 50 cents on the dollar. If they didn't take it, he would just drag through court. So, you know, they'd go bankrupt waiting for a long time," said Res.

Asked by USA Today in 2016 about contractor complaints, Trump said he docked companies pay if the Trump Organization was unhappy with their work.

"Let's say that they do a job that's not good, or a job that they didn't finish, or a job that was way late. I'll deduct from their contract, absolutely," Trump said.

If that strategy worked in the past, it may no longer be effective, according to Perry, who said, "there's a general loss of patience by litigants, and more importantly the judiciary, with some of these delay tactics and gamesmanship."

"There's been more of a 'rocket docket' with some of these matters than you might otherwise see," Perry said.

Special master in Mar-a-Lago documents probe

Five blocks south of the state criminal court building is the Brooklyn Bridge, which on the outer-borough side runs past another federal courthouse. The building's atrium is named for Raymond Dearie, the semi-retired judge who is serving as special master in Trump's lawsuit against the federal government.

That suit was filed in August after the Justice Department served a search warrant at Trump's Mar-a-Lago home, seizing White House files, some of which were labeled "Top Secret." Trump has insisted the documents were in his possession lawfully.

Dearie is reviewing thousands of pages of documents seized by the FBI, with a mandate to identify which, if any, are subject to attorney-client or executive privilege.

Trial of Trump confidant Thomas Barrack

On the eighth floor of that Brooklyn court building, another federal judge is presiding over the ongoing criminal trial of billionaire businessman Thomas Barrack, a longtime Trump friend and adviser who served as chair of the 2016 Inauguration committee.

Barrack is accused of acting as an unregistered foreign agent in an effort to sway U.S. foreign policy in favor of the United Arab Emirates' interests. He has entered a not guilty plea in the case.

During the trial so far, jurors have heard from former Trump administration Secretary of State Rex Tillerson, who was called as a witness, and have been shown emails and text messages sent to and from Trump administration officials.

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