He’s driven a taxi cab, played in a band and protested the Vietnam War. As a New York City judge, Arthur Engoron has resolved hundreds of disputes, deciding everything from zoning and free speech issues to a custody fight over a dog named “Stevie.”

Now, in the twilight of a distinguished two-decade career on the bench, the erudite, Ivy League-educated judge is presiding over his biggest case yet: deciding the future of former President Donald Trump's real estate empire.

Last week, Engoron ruled that Trump committed years of fraud by exaggerating his wealth and the value of assets on financial statements he used to get loans and make deals. As punishment, the judge said he would dissolve some of Trump's companies — a decision that could cause him to lose control of marquee New York properties, like Trump Tower.

Starting Monday, Engoron will preside over a non-jury trial in Manhattan to resolve remaining claims in New York Attorney General Letitia James' lawsuit against Trump, his company and top executives. He will also decide on monetary damages. James' office is seeking $250 million.

Trump, who is listed as a potential witness and could end up face-to-face with Engoron in court, called the judge's fraud ruling “the corporate death penalty.” He referred to Engoron as a “political hack" and said his would appeal.

“I have a Deranged, Trump Hating Judge, who RAILROADED this FAKE CASE through a NYS Court at a speed never before seen,” the 2024 Republican frontrunner wrote on his Truth Social platform.

Through a court spokesperson, Engoron has declined to comment on Trump's barbs. He is barred from commenting to the news media about the case.

Trump typically hasn't gone to court in the many cases involving his company. He was absent from a criminal trial in which the Trump Organization and one of its top executives was convicted of tax evasion and skipped a civil trial in which he was found responsible for sexually assaulting the writer E. Jean Carroll. But asked Friday if he planned to be at the New York trial, Trump said: “I may. I may.”

Engoron, a Democrat, has ruled repeatedly against Trump in the three years he's been presiding over James' lawsuit. He's forced Trump to sit for a deposition, held him in contempt and fined him $110,000.

Now, Engoron is poised to permanently disrupt the collection of skyscrapers, golf courses and other properties that vaulted Trump to fame and the White House.

At a hearing in the case last Wednesday, the day after his ruling, Engoron offered “a little bit of New York humor" to break the tension. He repeated an oft-told story about a judge who ended up agreeing with everyone who spoke in his courtroom.

Engoron, a fan of puns and pop culture references, routinely turns to humor — even in the gravest of hearings and decisions.

“We certainly can use it today,” Trump lawyer Christopher Kise said.

Engoron, a few years younger than Trump at 74, spent his early years in Queens, about 3.8 miles (6 kilometers) east of the former president's childhood home.

Engoron's family later moved to East Williston on Long Island, where he ran track and wrote for the student newspaper at The Wheatley School, a public high school in Old Westbury, New York, and graduated in 1967.

A proud alum, Engoron is the founder and director of the school’s alumni association and writes an online newsletter with news about fellow graduates who’ve nicknamed him the “Mayor of Wheatley.” He even posted a link last year to an article about his involvement in the Trump case.

At the end of one newsletter, he posted a quippy call to action: “Please send me your autobiography before someone else sends me your obituary.”

Engoron first made headlines in 1964, when he and three friends won the grand prize in a “Banner Day” contest where the New York Mets, then just two years into their existence, invited fans to parade across the field carrying banners painted with creative messages about the team.

In an early sign of Engoron's irreverence, the message was a take off on a popular political quote from the era: “Extremism In Defense Of The Mets Is No Vice.” Engoron was just 15 at the time.

While attending Columbia University in the 1960s, Engoron drove a taxi — a fact he revealed a decade ago while ruling against then-Mayor Michael Bloomberg's plan to expand yellow cab service outside New York City. A state appeals court later reversed that decision.

Engoron's rulings are rife with biographical information, part full-disclosure, part nostalgia. He revealed in one decision that he participated in “huge, sometimes boisterous, Vietnam War protests.” He’s also described himself as a free-speech absolutist and said he's been a member of the American Civil Liberties Union since 1994.

Engoron got his law degree from New York University in 1979. He's worked as a litigator and was a law clerk for 11 years for a judge in the same court where he now sits. Engoron also taught piano and drums and played keyboard in what he describes as a “moderately successful” bar band. He's been married three times and has four children, according to his Wheatley alumni page biography.

Engoron joined the bench in 2003 as a judge on the New York City Civil Court, which handles small claims and other lesser-stakes lawsuits. In 2013, he was appointed an acting justice of the state’s trial court and ran unopposed for a permanent post in 2015. His term runs until 2029, though New York requires judges at his level retire when they turn 76.

A former law clerk, Michelle Bernstein Ravenscroft, said she remembered Engoron being “kind and approachable and that he was very invested in making sure his clerks had a good learning experience with him.”

Engoron frequently peppers his rulings with song lyrics, movie quotes and the occasional New York City history lesson. He's quoted Bob Dylan and Shakespeare and movies like “City Slickers” and the Marx Brothers classic “Duck Soup.” He signs them with a logo of sorts, his initials, AE, drawn together in a circle.

In 2017, Engoron turned to the Frank Sinatra hit “Love and Marriage” which, the song notes, “go together like a horse and carriage” for a ruling restricting protests on horse-drawn carriages in Central Park. He punily titled a subsection “Balancing of the Equines, er, Equities.”

In a 2015 ruling on the custody of “Stevie” — a female, mixed-breed, part Basenji — Engoron offered a philosophical discussion of the rights of animals — or lack thereof — while reversing his previous ruling that sought to do what was in the pet’s best interest.

“Conferring rights on animals would create the ultimate slippery slope,” he said, reasoning that “if dogs were deemed to have rights, why not cats, raccoons, squirrels, fish, ants, cockroaches? Could you be imprisoned for swatting a fly? Where will it all end?”

In another ruling, Engoron said New York’s review process for new housing “seems like Rube Goldberg, Franz Kafka, and the Marquis de Sade cooked it up over martinis.”

Engoron has been involved in Trump-related cases since 2020, when he was assigned to intervene in quarrels among Trump’s lawyers and James’ office over demands for evidence and the direction of her investigation.

Trump’s lawyers wanted James’ lawsuit moved to a judge in the court’s Commercial Division, which is set up to handle complex corporate litigation, but an administrative judge kept the case with Engoron, citing his experience with the matter.

Back in the courtroom last Wednesday, as Trump's lawyers reached rare consensus with James' office on procedural issues, Engoron dispatched with one last quip.

“I knew this case would be a love fest," he said.