The man charged with ruling on Donald Trump’s property empire is no stranger to court battles with the former president.

Since Arthur Engoron began presiding over cases linked to Mr Trump in 2020, he has forced him to sit for a deposition, held him in contempt of court and fined him more than $100,000.

Their running battle has given rise to a bitter enmity between the two men. Mr Trump has called him “unhinged” and “deranged”, and a “political hack”, while Mr Engoron has used official rulings to mock the former president using pop culture references.

In a footnote to his most recent ruling that Mr Trump had inflated his net worth, Mr Engoron quoted from the Marx Brothers film Duck Soup: “Well, who ya gonna believe, me or your own eyes?”.

The judgment found that Mr Trump had committed years of fraud by exaggerating his wealth and the value of assets on financial statements he used to get loans and make deals.

Mr Engoron said he would dissolve some of the former president’s companies - a decision that could cause him to lose control of his best-known New York properties, such as Trump Tower.

On Monday, the pair faced each other in court for a trial that will decide the future of the Trump Organisation and whether Mr Trump will be required to pay $250 million (£205 million) in damages sought by Letitia James, the New York attorney general.

Mr Engoron spent his early years in Queens, about 3.8 miles east of the former president’s childhood home.

He first made headlines in 1964, when he and three friends won the grand prize in a contest where the New York Mets, a baseball team, had invited fans to parade across the field carrying banners. Mr Engoron, then 15, scrawled an adaptation of a Republican quote about Communism: “Extremism In Defence Of The Mets Is No Vice.”

Later, while attending Columbia University, the future judge drove a taxi - a fact he revealed while ruling against then-mayor Michael Bloomberg’s plan to expand yellow cab service outside New York City.

In another ruling, he said he had once taken part in “huge, sometimes boisterous, Vietnam War protests.” He has described himself as a free-speech absolutist and a member of the American Civil Liberties Union since 1994.

Alongside his career as a legal clerk and judge, he has taught piano and drums and played keyboard in what he described as a “moderately successful” bar band.

Mr Engoron became a New York judge in 2003, handling small claims and other small lawsuits, before being appointed as an acting justice of the state’s trial court – a position he made permanent in 2015.

His term runs until 2029, although Mr Trump’s may be the last major case he oversees before taking retirement under New York law at 76.

After Mr Engoron was given control of the fraud lawsuit last October, Mr Trump’s lawyers have accused Ms James’ office of trying to “judge shop” for a more critical judgment.

In subpoena disputes related to the case, Mr Engoron had already forced Mr Trump to pay $110,000 in fines and sit for a deposition.

He has also issued rulings ordering the Trump Organization and its appraiser, Cushman & Wakefield, to hand over evidence, and required Mr Trump’s son, Eric Trump, to testify at a deposition.

Mr Trump and Mr Engoron have a shared love of the city of New York, where both have built their decades-long careers.

The former president generally splits his time between Florida and New York and avoids visiting “the swamp” of Washington where possible.

But the fraud trial in New York may force him to give up Trump Tower – his glass-and-steel flagship on New York’s Fifth Avenue nearly four miles from Mr Engoron’s Lower Manhattan courthouse.

Mr Engoron frequently peppers his rulings with song lyrics, movie quotes and the occasional New York City history lesson.

He has quoted Bob Dylan and Shakespeare and movies like City Slickers and signs off his rulings with his initials, AE, drawn together in a circle.

In 2017, Mr 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.

In another ruling, he 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.”