By Nada TawfiqBBC News, New York
Donald Trump's recent legal loss hurts him the most because it targets his very identity.
For decades, he marketed himself as a genius business mogul who made it big in one of the world's cutest cities.
That film — always tied to the New York deal production and fueled by relentless self-promotion — catapulted him to international fame, allowing him to reinvent himself first as a reality TV star and then eventually as the president of the United States.
But Judge Arthur Engron's ruling in a civil fraud case — involving inflation of property values and lying about financial statements to get better loan terms — undermines Mr Trump's entire story. It portrays him as a fraud and deals a huge blow to his business empire and wealth.
Donald Trump once remarked that the mind can overcome any obstacle. But what is this obstacle?
The ruling significantly curtails the Trump Organization's ability to do business in New York. He is personally barred from holding any directorship for three years and his company cannot take loans from financial institutions registered in the city during that time.
He has been hit with a huge financial penalty of $355m (£282m; €329m) – more than $450m plus one-off interest – more than he has cash on hand. His business will be regularly monitored by an independent monitor, with a separate independent compliance director signing off on key business decisions.
In the one bright spot for the former president and Republican front-runner, the Trump empire was spared the equivalent of a corporate death sentence — the revocation of its business licenses.
Mr Trump appeared to be reeling from decades of scandals and legal challenges that could have irreparably damaged others.
The nickname previously belonged to mob boss John Gotti after he won a series of high-profile acquittals in the 1980s. But today's ruling suggests that, like Gotti, Donald Trump may be out of luck.
Judge Engoron noted Mr Trump and the other defendants' lack of remorse and history of repeated and persistent fraud. In the case, he said, the examples of fraud at the company over a decade “shock the conscience beyond measure”.
Still, the defendants were unwilling to admit the error of their ways, he wrote: “Their utter remorse and remorse bordered on pathology.”
Unsurprisingly, Mr Trump sees things very differently. He says he built a “proper company” and denies he should be convicted of fraud because the banks have been fully repaid. He continues to repeat claims without evidence that his legal challenges are a conspiracy by elite Democrats to keep him out of the White House.
According to Mary Trump, Mr Trump's estranged niece, the judge's ruling puts an end to the Trump family legacy. “Today is an emotional day, but one thing is for sure: the Engoran decision is absolutely devastating for The Donald,” he wrote on social media.
The son of a real estate developer whose portfolio includes middle-class apartment buildings in the outer boroughs of Brooklyn, Queens and Staten Island, Mr. Trump always dreamed of making a name for himself among Manhattan's skyscrapers.
Seven years of construction from 1976-1983, including the eponymous Trump Tower, cemented his reputation as a real estate giant in New York. “Many sons can't escape their fathers,” he told The New York Times in 1983 — and at age 37, he already had.
It is true that the 1980s era of greed and excess was a prosperous time for a young developer with his ambitions.
Trump Tower, with its prominent location on 5th Avenue, put Donald Trump on the map. Once his reputation was established, he put his name on every project he did.
In the early 1990s, Donald Trump filed for several corporate bankruptcies and lost almost all of them.
It was around this time that Rich Herzlock, chief engineer in the Manhattan Borough President's office, worked with Mr. Trump and his organization on the Riverside South project, a redevelopment of a former rail yard on the Upper West Side.
He says Donald Trump has to “do everything or close to everything” to be seen as a successful real estate developer — especially one who built an empire out of his father's legacy.
“See that [potentially] “Dismembered and mutilated, I can't imagine it being anything less than an emotional horror,” he told the BBC.
It is not yet clear how Mr Trump will pay the nearly half a billion dollars he owes, and whether it will involve selling any assets or businesses to raise the money. His vast real estate empire in New York is valued at $490 million by Forbes, but has many properties across the country, including hotels, golf courses, condominiums and a winery.
He will appeal against the conviction, which will put the decision on hold until a higher court reviews the case.
But if he wants to avoid paying a fine or confiscation of his personal assets while the appeal process is over, he must either deposit the full amount within 30 days or obtain a costly bond.
Selling any of his prime Manhattan real estate would be a shame for the former president — and he won't make a decision.
Whether Donald Trump recovers from this financial shock or not, the outcome looks set to erode his wealth significantly.
Having always been an outsider, ruling in the city where he rose to the top was undoubtedly a great loss. In more than six decades in New York real estate, there's no one Mr. Trump has derided more than a “failure.”