Donald Trump's latest legal defeat in a New York court — a jaw-dropping $354 million judgment to claw back the proceeds of a decade of fraud, plus almost $100 million in interest — puts an exclamation point on an unprecedented losing streak in his home state.

Trump and his company have been winless in a series of costly, cascading high-profile legal battles in New York in the last 14 months. It has been a reckoning without precedent, with judges and juries alike concluding that Trump and his company have engaged in illegal behavior for years.

Trump's losses have come in state and federal court, civil and criminal, in rulings by juries and judges. A total of 30 jurors in three cases have unanimously ruled against Trump or his company. One of those juries was composed of citizens from heavily Democratic Manhattan, but two came in federal court in the Southern District of New York, with a pool of jurors from more politically diverse suburbs and exurbs. 

Trump frequently calls courts in New York "rigged," but his losing streak is "an indication of the strength of the cases" against him, not a reflection of bias, said Cardozo School of Law professor Alexander Reinert. 

"That string of defeats is an indication of the unlawfulness of his conduct," Reinert said, adding that Trump acts like "he doesn't think the law really constrains him, and I think he needs to understand now that it does."

He will soon face yet another New York jury in his March 25 criminal trial, the first ever of a former president.

The list of Trump's legal losses in New York is already lengthy:

• In December 2022, a Manhattan jury found two Trump Organization companies guilty of 17 felonies related to tax evasion. The company was ordered to pay a $1.6 million fine and the case landed its former CFO behind bars. 
• On March 30, 2023, a New York grand jury in Manhattan indicted Trump on 34 felony counts of falsification of business records.
• Five weeks later, a federal jury in New York found Trump liable for sexual abuse and defamation in one of two civil lawsuits filed by the writer E. Jean Carroll. Trump was ordered to pay her $5 million. 
• In September 2023, a state judge found Trump and his company liable for a decade-long fraud scheme in a pretrial ruling.
• In January, another federal jury found Trump liable for defaming Carroll. The jury awarded her another $83 million. 
• On Friday, the judge in the civil fraud case issued his final ruling, saying Trump must pay the state $354 million, plus nearly $100 million in interest.

The fact that these defeats have all come in the Big Apple is not lost on Trump. He railed against his hometown in comments outside a Manhattan criminal courtroom on Feb. 15.

"It's all rigged. It's a rigged state. It's a rigged city," said Trump, who has denied wrongdoing in each of his cases and claimed his accusers are targeting him for political gain.

Minutes earlier, Trump's lawyer in his state criminal case argued in court that the former president couldn't get a fair shake in New York. Trump has entered a not guilty plea in the case, which revolves around reimbursements for a "hush money" payment days before the 2016 election that temporarily bought the silence of an adult film star who claims she had an affair with Trump.

Trump attorney Todd Blanche cited Trump's recent cases, claiming "outsized and extraordinary media saturation" in New York. Left unsaid was that Trump himself often cultivated that media frenzy, making the courtroom doorways and halls of lower Manhattan a marquee backdrop for a presidential campaign that's at times indistinguishable from, and always intertwined with, his many legal fights.

Blanche proposed asking prospective jurors about their feelings toward Trump, potentially to build a case for demanding a change of venue.

"We can't ignore the elephant in the room," he said.

That statement echoed one made by Manhattan prosecutor Joshua Steinglass, who called Trump the "elephant not in the room" during jury selection for the criminal case against the former president's company in October 2022.

In that case, some prospective jurors who were ultimately excused said they didn't think they could set aside their opinions of the former president. One said, "I have total disdain for anything to do with Trump. Sorry." Another went a step further after saying jury duty could interfere with her travel plans: "And I also hate Donald Trump, if that is of merit."

A few expressed admiration and support for Trump, and nearly all pledged to set aside their biases in considering the case. At the end of the five-week trial, the 12 who were chosen took just over a day to find two Trump Organization companies guilty of 17 felony counts related to tax fraud.

In April 2023, a federal jury pool was once again probed about their political leanings and news consumption habits for the Carroll sexual abuse and defamation civil trial. Trump, though a defendant, declined to attend any of the proceedings, which lasted two and a half weeks. The jury of nine took just three hours to find Trump liable for sexually abusing and defaming Carroll, and awarded her $5 million.

Trump attended a trial in the same federal courtroom in January, when a new jury of nine considered evidence related to separate defamations of Carroll. Trump huffed and trumpeted disgust throughout the two-week trial, though he and his entourage got up and walked out of court minutes before the jury awarded Carroll another $83 million.

Friday's ruling by a state judge in Trump's civil fraud case brought the total Trump owes for bad deeds to more than half a billion dollars, with interest continuing to accrue.

"When I teach constitutional law, we do cover cases involving the president, but they tend to be about a president failing to disclose material to Congress, or involving their constitutional duties. There's nothing else like this," said Noah Rosenblum, a New York University professor of legal history. 

"There's nothing like it previously in American history."

Graham Kates

Graham Kates is an investigative reporter covering criminal justice, privacy issues and information security for CBS News Digital. Contact Graham at [email protected] or [email protected]