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The Big Apple vs the Big Orange

New York courts now look like the best chance of stopping Donald Trump’s return to the White House

Image: TNE/Getty

On Sunday, business was reported to be “brisk” in the gift store at the Trump Tower on Manhattan’s Fifth Avenue. In its solemnity, it reminded me of a souvenir shop at a religious shrine: shelves packed with T-shirts, baseball caps, mementoes and golf accessories, all celebrating the MAGA cult of personality.

In the starry eyes of true believers, this Midtown, 58-storey skyscraper is a pilgrimage site. For this, as if we could forget, is where it all began: on June 16, 2015, when Donald and Melania Trump descended that golden escalator to announce his first presidential candidacy and throw a Molotov cocktail into the swamp of history.

Now, nine years later, his third such campaign is in alarmingly good shape. Democrats I have spoken to are seriously rattled by the New York Times/Siena College national poll published last weekend, in which Joe Biden was five points behind Trump – the largest lead the presumptive Republican nominee has held in these particular surveys since entering politics.

One data point is especially worrying for the president: Biden is retaining the support of only 83% of those who voted for him in 2020, of whom 10% (amazingly) now say they will cast their ballot for Trump. In contrast, 97% of Trump’s 2020 supporters are sticking with the Lord’s Orange Anointed.

To make matters worse: the prospect of securing convictions in Trump’s four criminal cases before election day on November 5 is diminishing fast. In Georgia, the grand racketeering prosecution has been stalled by a tawdry row involving an affair between Fulton County District Attorney Fani T Willis and the lead prosecutor Nathan Wade (an argument about “optics”, not law, please note). In Florida, Judge Aileen M Cannon has delayed setting a trial date for the federal classified documents case.

Worst of all, the conservative-dominated US Supreme Court ruled last week that it would now consider Trump’s claim to total presidential immunity from prosecution for actions taken while he was in office. Which means that the big federal election interference case brought by special prosecutor Jack Smith will now be seriously, perhaps disastrously, delayed.

Judge Tanya Chutkan had originally set March 4 as the trial date. But it is now entirely possible that the case will not even start (assuming it starts at all) this side of polling day.

The Supreme Court might not deliver its judgment until the end of June or early July. Assuming it rules against Trump – probable, though not a certainty – he is still entitled to 88 days of preparation for Smith’s case. That would take us into October.

There is also a justice department rule forbidding actions that might interfere with the democratic process in the 60 days before an election. Whether this applies to a case already underway is a matter of dispute.

It may not surprise you that a whole new industry of podcasts has arisen, solely dedicated to Trump’s dizzying array of legal problems (if you want to go down that particular rabbit hole, I recommend Crooked Media’s Strict Scrutiny).

The bottom line is that the chances of Trump being convicted before the election are fading fast. This really matters because the polls suggest that Biden would pull ahead if his predecessor were actually found guilty of a criminal charge; and, more specifically, that more than half of swing-state voters would not vote for Trump in these circumstances.

So: there is a delicious symmetry in the fact that New York, the city that made Trump, is now also the city best placed to take him down when it really counts.

It was here, after all, that he invented himself as a playboy property developer: a walking symbol of brash late 1970s and 1980s greed; who made sure he was seen at Studio 54; who promised to “put some showbusiness into the real estate business”; who was mentored by New York Yankees owner George Steinbrenner and the Machiavellian, McCarthyite attorney Roy Cohn (whom he dropped when Cohn fell ill with Aids); who hated the Manhattan elite even as he longed to be accepted by them.

As Maggie Haberman puts it in her brilliant biography, Confidence Man: The Making of Donald Trump and the Breaking of America (2022): “The dynamics that defined New York City in the 1980s stayed with Trump for decades; he often seemed frozen in time there”.

If so, he has somehow forgotten that New York knows no mercy. At the time of writing, the “hush money” case brought by Manhattan district attorney Alvin Bragg still has a trial date of March 25, and Judge Juan Manuel Merchan has shown no inclination to procrastinate (since the case involves alleged crimes committed before Trump was elected, it is not affected by the Supreme Court’s antics).

Although the alleged payoff to porn star Stormy Daniels has attracted most media attention, the case is much more wide-ranging, embracing 34 felony counts involving the alleged falsification of business records and acts of interference in the 2016 presidential campaign.

Yes, this is not as serious as the indictments covering the “Stop the Steal” conspiracy in 2020. But, if found guilty in Manhattan, Trump could go to prison for up to four years. And – crucially – this is all happening very soon.

On top of which: the pitiless wheel of fortune that looms over the New York skyline threatens to do something that would hurt Trump much more than criminal convictions; namely, to take all his money away. In two civil cases involving sexual abuse and defamation, he has already been ordered to pay the writer E Jean Carroll a total of $88.5m.

Even worse for Trump was the instruction on February 16 by Judge Arthur Engoron to pay $354.9m for fraudulently overstating his net worth to deceive lenders – more than $450m including interest. He was also barred from holding any top roles in a New York company for three years, including parts of the Trump Organization.

If New York is a monster, this is its roar: I’m gonna take your money, sucker. Which means, in practice, his real estate.

It has always been almost impossible to work out how cash-rich Trump actually is: Forbes estimates that he has around $413m to hand, close to what he himself testified in April 2023 (“substantially in excess of $400m” – you can always ignore words like “substantially” when he uses them).

Ever the hustler, the former president had been counting on a perfectly timed windfall of $3-4bn from the merger of Trump Media & Technology Group, which owns his Truth Social network, with a special purpose acquisition company called Digital World Acquisition, formed so it could be publicly floated.

But that payday has now been nixed, at least for now, by (you guessed it) yet another lawsuit brought on February 28 accusing Trump of “wrongful 11th hour… manoeuvring” to “drastically dilute” the value of shares held by his co-founders.

In another glorious symmetry, those co-founders, Andy Litinsky and Wes Moss, are former contestants on Trump’s reality show, The Apprentice.

Which means that, unless Trump can come up with $454m by March 25, New York Attorney General Letitia James will be entitled to play bailiff and start seizing his assets. In the city itself, she has explicitly mentioned Trump’s 40 Wall Street skyscraper; he has a 30% stake in 1290 Avenue of the Americas; some units in Trump Park Avenue and other Trump-branded apartment buildings; and – of course – the commercial space and his own triplex apartment in Trump Tower itself.

For true believers, the loss of this shrine in the sky would be like the Vatican being repossessed. It is no accident that Christopher Nolan chose the tower as the location for Wayne Enterprises in The Dark Knight Rises. The mythology of Gotham clings to its shimmering walls.

And – of course – if the building and others like it were indeed seized during the campaign, Trump would present the confiscation as just the next phase of the witch hunt, the supposed “Deep State” persecution which he has made a metaphor for the suffering of his supporters.

“I am your justice,” he said at an event in Maryland last year. “And for those who have been wronged and betrayed: I am your retribution”.

All the same: it would hurt like hell. Remember Mark Twain: “In Boston they ask, how much does he know? In New York, how much is he worth?”

It would get to him, as many things do. It would diminish him, deplete his political immunity system and puncture the big boss image that is so essential to his narrative.

Alina Habba, Trump’s lawyer, has said that if James gets her way, “New York is screwed”. To which New Yorkers reply: it’s your boss who’s about to get screwed, honey.

It is apt that both Trump’s The Art of the Deal and Tom Wolfe’s The Bonfire of the Vanities were published in 1987. The former is a guide (though nobody knew it at the time) to the lies, bombast and post-truth that would underpin strong-man leadership in the US and elsewhere in 2016 and beyond. The latter, one of the great post-war novels, uncovered the deceit, status fixation and dangerous social pathologies that underpinned the glamour of 1980s Manhattan and the “Masters of the Universe”.

Wolfe’s main protagonist, Sherman McCoy, is a much more sophisticated figure than Trump, a superstar bond trader rather than a property developer. But they share a cruel indifference to the consequences of what they do, the damage they so recklessly cause.

The point, according to McCoy, is to do whatever is necessary to avoid the sweat and tears of ordinary people’s lives: “If you want to live in New York… you’ve got to insulate, insulate, insulate, meaning insulate yourself from those people”.

Trump’s hypocrisy is even greater, since he claims – absurdly but with depressing success – to represent the left-behind working-class and the resentful dispossessed of deindustrialised America. Like McCoy in the novel’s final pages, he has ended up a “professional defendant”.

Yet he could still be president again. Of that there is absolutely no doubt. Those expecting “normality” to reassert itself, for the non-existent pendulum to swing back, are deluding themselves and wasting time.

If Biden is to win in November, he has to ditch the old playbook and accept the absolutely new paradigm of the post-2016 world.

In this, at least, he has a friend in the city of New York. Uniquely in America, it is not backsliding in its campaign to convict Trump of multiple felonies. It is not relenting in its crusade to strip him of his wealth. It is, true to form, taking care of business.

Come on, Manhattan: do your worst.

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