The audacity of Donald Trump is perhaps one of the characteristics a person needs to really make it in New York, but the former Fifth Avenue resident has never been truly accepted by his home city.
There are other personality traits that might have helped, had he possessed them.
Like so many people around the world, the island of Manhattan held a certain magnetism to a young Donald Trump.
The pull was only from across the East River, but the boy from Queens had more means than most to make it in the place that tempted the willing into believing the great American dream could come true.
Donald Trump would make his mark on the city, getting richer as it did, regularly featuring in gossip columns, hosting lavish parties and living in the golden tower named in his honour.
But there are things money cannot buy.
It can't buy honesty or integrity, and if you don't have those things and you end up with a lot of power, you might also end up in a lot of trouble.
This week, Manhattan became the first district to indict Donald Trump on criminal charges.
Media gathered from around the world to write about the historic moment that played out in the Manhattan Criminal Courthouse because this time, the person being fingerprinted was a former United States president.
But there was no denying that those watching from around the borough were acutely aware he was also a former resident.
Donald Trump wanted so desperately to impress Manhattan and be accepted by its elite but ultimately, he never ascended to the status he craved.
When he fled to Florida in 2019, he rolled into his compound at Mar-a-Lago and into his supporter heartland, finally living in a place where the people not only accepted him, they adored him.
They talk of being willing to die for him.
Nearly four years later, the state of New York and, specifically, the District of Manhattan finally came calling, but it wasn't to give him the satisfaction of acceptance. It was to place him under arrest.
Manhattan was the birthplace of Donald Trump the tycoon, and it's there he will first be put on trial.
Making it in Manhattan
Donald Trump's ride down the golden escalator at Trump Tower in 2015 was a defining moment in American politics as the brash billionaire and reality television star announced his candidacy for president.
In his speech that day, he told the crowd of devoted supporters his father had warned him not to come to Manhattan.
Fred Trump had told his son, who was already a millionaire, that the island at the centre of the world was indeed the "big leagues".
Donald Trump was only more determined.
"I gotta build those big buildings," he said.
In 1984, when he had just opened Trump Tower and was rapidly developing real estate projects across the city, author William E Geist wrote in New York Magazine that some New Yorkers would run up to the young businessman and touch him for the chance of his good fortune rubbing off on them.
Others were not so convinced.
"They see him as a rogue billionaire, loose in the city like some sort of movie monster, unrestrained by the bounds of good taste or by city officials to whom he makes campaign contributions, ready to transform Midtown into another glass-and-glitz downtown Houston, with Central Park for parking," he wrote.
The previous decade had seen the city gripped by the worst financial crisis in its history. In the 1980s, murder rates jumped, and there was a sense of desperation.
Donald Trump used it to his advantage and, on the promise of economic rejuvenation, secured tax breaks that allowed his personal wealth to skyrocket.
The average American may have been looking up at him, but Manhattan elites were looking down.
Susan Mulcahy was a Page Six columnist in the 70s and 80s, and Donald Trump made for a great story.
"Trump was so outrageous — and outrageously tacky — it was a constant temptation to write about his antics, particularly because he thought he was the height of sophistication," she wrote in Confessions of a Tabloid Scribe.
"He didn't seem to understand, for instance, that if he wanted the respect of Manhattan's cognoscenti, he should have left the beloved Bonwit Teller building in place on 57th Street, or at least given the bas-relief sculptures on the department store's façade to the Metropolitan Museum, which wanted them for its collections.
"He smashed them to bits."
Trump the brand
While Donald Trump was building his wealth, he was also building a brand.
No longer satisfied with success on the island of Manhattan, at 40 years of age, Trump released The Art of the Deal and introduced himself to America as a brilliant businessman.
It was 1987 and life was good, but the next decade would test the deal-maker.
His real estate empire was in debt, he needed cash, and the book allowed Trump to put a price on his name.
Eventually, there were Trump resorts he did not build. Then golf clubs and food companies. Trump steaks. Trump suits. Sunglasses. Underwear. Colognes.
It was a low-risk, high-reward strategy that proved far more lucrative than the over-leveraged development deals which saw him file for corporate bankruptcy four times.
Talking to the Wall Street Journal about his escape from financial ruin in the 1990s, Trump said:
"I had some banks that I was negotiating with that were fabulous people. I also had some very terrible people that I was dealing with, and had I not been more terrible than them, I might not be sitting here talking to you right now."
Donald Trump sold himself on being a deal-maker and a bullish leader who got what he wanted.
His determination changed the face of New York City.
Manhattan has long known what Trump was willing to do to succeed — and to survive.
Now its criminal court will test how far he was willing to go to get to the White House.
NYC rejects President Trump
On Wednesday, as he was arraigned, the former president was able to summon a moderately sized crowd of supporters outside the courthouse.
Compared to a Trump rally, it was nothing.
On the campaign trail in 2020, it was not uncommon to see Trump supporters driving by Joe Biden rallies making their feelings known, but it was rare to see the reverse.
This week, New Yorkers showed up, and Trump's fans were face-to-face with a group of people who want him behind bars and were not afraid to make noise about that.
They told the ABC that the Manhattan indictment was the former president's "worst fear because he's always yearned for New York's love and he's never had it".
Trump supporters Marjorie Taylor Greene and George Santos lasted minutes, quickly swamped by the press but also drowned out by the chants, whistles, cowbells and the snare drums from over the fence.
The anti-Trump anthem FDT played on repeat all day.
In 2016, both presidential candidates were from the state of New York — Hillary Clinton won 59 per cent of the vote in the state.
Then-BBC journalist in New York Nick Bryant wrote that there were several moments in that campaign when he witnessed a different Donald Trump:
"After spending much of the past year or so watching and travelling with Donald Trump, I've been struck by how his physical demeanour changes when he appears in public in New York City — not in the atrium of Trump Tower, his personal fiefdom, where his incendiary rhetoric ricochets off the marble walls, but rather when he steps outside that self-congratulatory echo chamber."
Bryant recalled the Al Smith dinner in the final week of the campaign.
"Faced with a hostile crowd of New York's white-tied elite, who booed parts of his speech, Trump seemed almost sheepish. The catcalls of rich New Yorkers seemed especially wounding, and it was the first time during the campaign when he looked like he had been cowed," he wrote.
In 2018, Trump's Art of the Deal ghostwriter Tony Schwartz noted: "No amount of money, fame or power has been enough to win him the respect he so insatiably craves."
Even becoming commander-in-chief was not enough.
And it wasn't just the city's uber-wealthy who he failed to impress as president.
Trump's administration was building a wall along the US-Mexico border while New Yorkers were tearing down the signs that branded their buildings with his name.
More than a third of the population of New York City was born outside the United States, and the city had long moved to provide a level of protection to undocumented workers.
There are countless chapters to the story of Donald Trump's relationship with his home city, and in many of them, he is either making money or exerting the power of the highest office in the land.
But in the latest chapter, the people of New York are in charge.
Trump in the defendant's chair
Donald Trump was only in court for 45 minutes as he and his legal team learned about the details of the charges a grand jury of New York City residents had voted to indict him with.
Stories that have followed the former president for years are now at the heart of his legal battle: alleged hush money payments were made to prevent them from ever being made public.
It is alleged that Trump and others covered up a series of payments made to adult film star Stormy Daniels, another woman and a former Trump Tower doorman by falsifying financial documents.
To elevate the charges to felonies, District Attorney Alvin Bragg alleges that was done in order to conceal other crimes.
The indictment does not detail what those were but, in a press conference, Bragg alluded to violations of both state and federal election legislation and tax laws.
Legal experts are divided on the strength of the case; from the safety of Florida, Trump told his supporters there simply was "no case".
This indictment may not be the last to force Trump to defend criminal charges, but it is the first and, potentially, the most personal.
Because now it's there in black and white, scanned and shared on court documents that despite all his attempts to win their acceptance, it is, in fact "The People of the State of New York against Donald J Trump".
