A Short History of the Trump Family

The​ most enduring blight left behind by Donald Trump, long after he has smashed things up, will be the pile of books devoted to trying to make sense of him. It will grow after investigative journalists have spent years diving for hidden records, exploring subterranean corporations and foreign partners but never reaching the dark ocean bottom. It will continue after political scientists have trekked through mountain ranges of survey data seeking the precise source of his magnetic attraction for the aggrieved white lower-middle and working classes. It will outlast the pundits holding forth on TV, collecting lecture fees and cranking out bestsellers that retail inside dope gleaned, single-sourced and second-hand, from somewhere near the elevators of Trump Tower. It will not be stemmed even after the memoirs of Trump’s associates, unreliable narrators in the spirit of their leader, have been removed from the remainder bins in used bookstores.

A week after the inauguration, Nineteen Eighty-Four and The Origins of Totalitarianism were number one and number 36 respectively on the US Amazon bestseller list, but the true-life Donald J. Trump story has more to do with what Scott Fitzgerald called ‘foul dust’ than with ideas or ideology. Reckoning with Trump means descending into the place that made him. What he represents, above all, is the triumph of an underworld of predators, hustlers, mobsters, clubhouse politicians and tabloid sleaze that festered in a corner of New York City, a vindication of his mentor, the Mafia lawyer Roy Cohn, a figure unknown to the vast majority of enthusiasts who jammed Trump’s rallies and hailed him as the authentic voice of the people.

The notion of a Trump literature begins, appropriately, with an imaginary novel, 1999: Casinos of the Third Reich, contrived by Kurt Andersen, an editor at Spy, a New York magazine of the 1980s and 1990s. Over several months in late 1989 and early 1990, Andersen kept referring to the non-existent Casinos of the Third Reich and its implausible protagonist, Donald Trump, whose narcissistic exhibitionism offered a never-ending source of unintentional self-satire. ‘Who’s my toughest competitor – if not in content, only in style?’ he asked. ‘Prince Charles,’ he answered. ‘I’m thinking of becoming an entertainer,’ he also said. ‘Liza Minnelli gets $75,000 a night to sing, and I’m really curious as to how I would do.’ ‘Yes,’ Andersen wrote, ‘in the blockbuster 1999: Casinos of the Third Reich, it’s nobleman-lounge singer Donald Trump!’ Andersen simply quoted Trump, referred to Casinos of the Third Reich and sat back. Trump did all the work. The fabulous novel had no plot and the protagonist’s character didn’t develop – just like in real life. Spy assumed its readers were in on the joke about the ‘short-fingered vulgarian’. (Marco Rubio flung Spy’s slight against Trump in a debate, without noting its provenance in the defunct magazine, if indeed he knew it. Trump heatedly replied: ‘If they’re small something else must be small. I guarantee you there’s no problem.’ The Trump spectacle often ends with insult imitating satire.)

Fred Trump, Donald’s father, was a king of Queens; the Donald became a joker in Manhattan. In search of fame and greater fortune in the big city, he set out from the family mansion with its 23 rooms, nine bathrooms and, at the front, four white columns adorned with a confected family crest. A Cadillac and a Rolls-Royce were parked in the driveway, guarded by two cast-iron jockeys. Even in Queens, it was a world apart. ‘“Be a killer,”’ Fred Trump, ‘who ruled all of us with a steel will’, told him. Then he said: ‘“You are a king.”’

Trump wasn’t looked down on in Manhattan because he was a parvenu, a dressed-to-kill bridge-and-tunnel bounder from an outer borough. New Yorkers hardly have a bias against aspiring newcomers. The musical Hamilton exalts a classic New York story of a brilliant young immigrant rising in a mercantile culture. (‘I hear it’s highly overrated,’ President-elect Trump tweeted last November after the cast addressed Vice President-elect Mike Pence, as he was leaving the theatre, calling on the new administration ‘to work on behalf of all of us’.) Walt Whitman sang in ‘Mannahatta’ of a city ‘liquid, sane, unruly, musical, self-sufficient’. Trump wished to be more than accepted in Manhattan: he wanted to be adored, there and only there, and came to despise it in all its diversity and cacophony when time and again he was rejected. ‘I want to wake up in a city that doesn’t sleep and find I’m king of the hill, top of the heap.’ The lyrics of Frank Sinatra’s standard ring out like a mocking chorus from the Yankee Stadium when the hometown wins. Poor Trump, who thought the song should be his anthem, could never shake his ‘little town blues’. His humiliation at his failure ‘to make it there’ is at the heart of his vengeful compulsion to wreak humiliation on those he fears will belittle him. The uncontrollable anger that unleashes a regular flood of insults derives from his profound feeling that he has been, is being and will be diminished. In a constant state of alert and hurt, he victimises others because he burns with the feeling that he is the true victim. Every time his outlandish behaviour turns him into the butt of a joke, especially at the hands of sources associated with New York, from Spy’s jibes to Alec Baldwin’s impersonation on Saturday Night Live, his rage is stoked. Portraying himself as the innocent party he lashes out, a narcissistic reflex but also a tactic he learned from Roy Cohn.

Resentment born of entitlement, of the feeling that he was being treated as an inferior though he knew he was superior, was an inadvertent and inverse link with the lower-middle-class whites who fled Queens and Brooklyn in the 1950s and 1960s for the Long Island suburbs to escape black migration. They went one way and Trump another, but both were repelled by Manhattan’s racial liberalism, which was seen as an insult to and impingement on their own status from those above and below them.

Trump’s loathing and bullying are among the few things he came by honestly: they were part of his inheritance. Fred Trump was arrested for participating in a violent Ku Klux Klan rally in 1927; he had Mob ties and flagrantly discriminated against blacks when renting out housing. Woody Guthrie, his most famous tenant, wrote about his landlord in the first literary work on a Trump, ‘Old Man Trump’:

I suppose
Old Man Trump knows
Just how much
Racial hate
he stirred up
In the bloodpot of human hearts
When he drawed
That colour line
Here at his
Eighteen hundred family project

In 1988, Spy conducted a national poll, the first ever on the presidential potential of Donald Trump. Offered a list of non-candidates, voters were asked: ‘Who are you most disappointed isn’t running for president?’ Trump got 4 per cent of the vote. Tellingly, Spy discovered the celebrity’s irreducible base: ‘In terms of level of education, the voters who most favoured a Trump candidacy – with a 9 per cent rating – were those whose minds remain uncluttered by any learning beyond junior high school.’

Trump was already among New York’s stock cast of colourful characters, one of Spy’s ‘top ten jerks’, joining notorious loudmouths of the era such as the New York Yankees’ bullying owner George Steinbrenner (another Roy Cohn client). From the Bronx to the Battery, opinion on Trump set as hard as the cement on his construction sites and as fast as he had ordered underpaid Polish immigrant construction workers in 1980 to jackhammer the Art Deco friezes on the Fifth Avenue Bonwit Teller building to make way for his tribute to himself, Trump Tower, a slab of banality which resembles an elongated flat-screen TV. He had promised to preserve the reliefs for the Metropolitan Museum, but after blasting them to smithereens to widespread condemnation the Trump Organisation issued a press release declaring that the sculptures were ‘without artistic merit’. Through a PR agent, Trump claimed the demolition was a matter of aesthetic judgment and, he added, cost him $500,000, no doubt a round number pulled out of a hat. In the New York Times the PR spokesman identified himself as ‘John Barron’. In the Associated Press story the same publicity man called himself ‘Donald Baron’ and was quoted as saying that ‘the merit of these stones was not great enough to save them.’ Both ‘John’ and ‘Donald’ were Trump. ‘What do you think? Do you think blowing up the sculptures has hurt me?’ he asked Vanity Fair a decade later.

Who cares? Let’s say that I had given that junk to the Met. They would have just put them in their basement. I’ll never have the goodwill of the Establishment, the tastemakers of New York. Do you think, if I failed, these guys in New York would be unhappy? They would be thrilled! Because they have never tried anything on the scale that I am trying things in this city. I don’t care about their goodwill.

Then Trump fired the illegal immigrant labourers, ‘the Polish brigade’, after they’d completed their work, meaning that they were deprived of wages and benefits. The US Labor Department filed suit against him, a federal judge found him guilty of fraud, noting that his testimony was not credible, and eventually he paid a fine in a sealed agreement.

Donald Trump​ ’s universally disparaged image in Manhattan attained skyscraper heights at the turn of the 1990s, after his flamboyantly bungled real-estate projects, tabloid hijinks, manic club-hopping, flagrant Mob associations, cruel wife-dumping, outrageous defence of his housing discrimination, not to mention his purchase of screaming full-page newspaper ads demanding the death penalty for black youths accused of rape, the Central Park Five, who later turned out to have been innocent. ‘The banks call me all the time,’ he boasted. ‘Can we loan you money, can we this, can we that.’ But Trump had wildly run up $3 billion in debt. Now his grandiose Trump Shuttle airline crashed and burned. He lost his crown jewel, the Plaza Hotel. (‘They say the Plaza is worth $400 million? Trump says it’s worth $800 million,’ said Trump. ‘Who the hell knows what it is worth?’) His casino empire across the Hudson River in Atlantic City, his Taj Mahal, went belly up. (‘The most spectacular hotel-casino anywhere in the world’.) He declared bankruptcy four times in order to stiff his contractors and workers. Every financial house in the city spurned his plea to extend his loans. Rather than acceding to his childish demands after meetings at which he brandished newspaper clippings about his antics instead of financial papers, the banks put the profligate Trump on an allowance like an irresponsible adolescent. He had to sell virtually everything, including his yacht, the Trump Princess, which he had purchased from the shadowy Saudi arms trader Adnan Khashoggi. Trump threatened to sue a journalist at the Wall Street Journal for accurately reporting his collapse, one of his many attempts to intimidate the press, and another technique he learned from Roy Cohn.

‘Wa-a-a-a-h! – Little Donald, Unhappy At Last – Trump’s Final Days,’ crowed the cover story in the August 1990 issue of Spy. The illustration depicted him as a wailing toddler. The story inside the magazine, ‘A Casino Too Far’, featured a fictional scrapbook of newspaper clippings carrying ‘the brash tyro’ forward to his miserable future in 1996, bloated, balding and broke, ‘doing a little consulting for the Sultan of Brunei’.

Trump never fitted the mythology of rugged individualism he mimicked and tried to sell as intrinsic to his brand. Launched as a front and junior partner for the tainted Fred Trump in Manhattan real estate, he had been on gaudy display in New York since he first crossed the Queensboro Bridge with $14 million from his father. ‘My father gave me a very small loan in 1975 and I built it into a company that’s worth many, many billions of dollars,’ he lied during one of the presidential debates. Born with a silver spoon in his mouth, he insists that he has pulled himself up by his bootstraps. But, as well as staking him to launch his real-estate career, when the Taj was sinking like Donald’s own private Titanic, Fred Trump rushed to the casino to buy $3.35 million in chips to buoy his flailing child, who used the money to avoid default by making an interest payment he wouldn’t otherwise have had the liquid reserves to meet. A straight loan would have put Fred Trump in the lengthy queue of creditors. With his loan in the form of chips he could redeem it as soon as his son had the capital. The New Jersey Casino Control Commission ruled a year later that Fred Trump had engaged in an illegal loan and that Donald should return it, which would have forced him into instant bankruptcy. The Trumps blithely ignored the finding and instead paid a meagre $65,000 fine, though the manoeuvre failed to save the casino.

But Trump evaded the fate Spy had foreseen for him. His genius was to promote his clownishness, so that the headlines fed to the New York Post consisting of make-believe quotes from his then mistress Marla Maples (‘Best Sex I’ve Ever Had’) became a PR platform for the licensing of his celebrated name to murky investors from Russia, China and Saudi Arabia who were looking for an American frontman. His salvation was a double play of a con.

The glitzier the gigantic bronze block capitals of his name staring down Fifth Avenue and across Central Park, the more secure New Yorkers felt in their contempt. Trump Hotel was strictly for out-of-towners seeking to be sprinkled with ersatz gold dust. Trump could never escape being a ‘Queens-born casino operator’, as Spy stamped him. But he wasn’t scorned only for his unrelieved vulgarity. The reaction to him wasn’t the antique snobbery Edith Wharton dissected in her society novels, but the worldly perspicacity of New Yorkers high and low. Trump’s quest for respectability only deepened his problems. It wasn’t that he had missed his moment like the passive Newland Archer in The Age of Innocence, but that his love was unrequited because New York found him repellent despite his incessantly harassing courtship.

Trump’s reality TV shows, The Apprentice and The Celebrity Apprentice, were fantasy projections of his dominance in the city in whose eyes he was obviously not the master of the universe. From 2004 to 2015, he played on TV the persona that he intended Manhattan to worship. Of course, ‘reality’ in Trump’s reality TV wasn’t real. In every episode he acted out dramas of control over submissive contestants seeking his favour, wilting at his denial of it and fawning at his approval. Under Trump, winning was the road to serfdom. The subtext was pathos, not only on the part of the supplicants but also in the boss’s trademark phrase, ‘You’re fired.’ No matter how many people Trump rejected, he couldn’t force his own acceptance.

If​ there is one subject that has unified discordant New Yorkers over the past five decades, it has been Trump. In 2016, he lost 87 per cent of the vote in Manhattan, and most of those who voted for him probably did so with distaste, casting their loyal Republican votes for a man who for most of his life donated money to Democratic candidates in a Democratic city. (Trump also lost in Queens, carrying only 22 per cent of the vote; in Brooklyn, he won less than 20 per cent; and in the Bronx, about 10 per cent.)

After the election, Trump’s manic sensitivity to his rebuff by New Yorkers exploded in his id’s unfiltered outlet, his trigger-happy Twitter account. When Vanity Fair headlined a review of his restaurant ‘The Trump Grill Could Be The Worst Restaurant In America’ he fired off an early morning tweet directed at its editor, Graydon Carter, who not coincidentally had been co-editor of Spy. ‘Has anyone looked at the really poor numbers of Vanity Fair Magazine. Way down, big trouble, dead! Graydon Carter, no talent, will be out!’ Immediately, Vanity Fair had its biggest one-day increase in subscriptions. Once again, Trump had foolishly exposed his thin skin. For him, Manhattan has always been the opposite of what home was for Robert Frost, ‘the place where, when you have to go there, they have to take you in.’ Wa-a-a-a-h!

Winning the presidency was never a deep desire, more a branding scheme that spun out of control, but Trump has tried to turn his victory into a means to compel New Yorkers finally to genuflect. Washington had never held the slightest allure for him – until now when it is leverage over New York. Even so, Washington is strictly Palookaville, a nowhere town for grown-up student council presidents. There is only one City on a Hill for Trump, the city that doesn’t sleep, where a perpetually wide-awake collective eye fixes its unwavering judgment on him. ‘It’s up to you, New York, New York.’ President Trump in his eyrie is King Kong defying the gaping city below. But in contrast to the original movie, there is no tragic anti-hero: he lacks the giant ape’s sympathy for a beautiful young woman, and it won’t be beauty that kills the beast.

After his nomination for president, Trump talked about his fondest wish: winning New York State. ‘We are going to win this state,’ he proclaimed, adding that he had won the Republican primary there ‘because nobody knows me better than New Yorkers’. Unfortunately for him, New Yorkers did know him. But earlier in the campaign he had expressed another wish. Nothing he said during the campaign more succinctly reflected his furious and damaged narcissism than his dream of committing cold-blooded murder and getting away with it. ‘I could stand in the middle of Fifth Avenue and shoot somebody, OK, and I wouldn’t lose any voters, OK?’ The ‘somebody’ he wanted to kill could be any New Yorker. But why did he ask twice if it was ‘OK’? His statement expressed three unconscious desires at once: striking back at New Yorkers; breaking the rules without consequence; and gaining adulation from the fans for whom he can do no wrong. Shooting ‘somebody’ on Fifth Avenue, however, presumably would not win him voters on Fifth Avenue, which is where he lives.

‘We don’t win anymore,’ Trump lamented. His reverent followers took his omnipotent image from his reality show as the reality and his anger as something felt on their behalf. They didn’t understand his inner injury. Rousing the crowds at his rallies to a fever pitch – ‘knock the crap out of them’ – he encouraged an atmosphere of violence and fear. Watching Trump incite his pitchfork revolt, New Yorkers were merely astounded that others couldn’t recognise his all too familiar stuntmanship. He knew he had to cross the Hudson to find true believers, but the further into Duck Dynasty territory he ventured the more it felt like banishment to Queens. In winning he had not won. He couldn’t get over it. Nothing had changed for him since the interview he gave to Vanity Fair in 1990 in which he said: ‘There are two publics as far as I’m concerned. The real public and then there’s the New York society horseshit. The real public has always liked Donald Trump. The real public feels that Donald Trump is going through Trump-bashing. When I go out now, forget about it. I’m mobbed. It’s bedlam.’ Trump’s most deeply felt grievance 26 years later wasn’t that he lost the popular vote by 2.8 million – he dismissed these votes as fraudulent. Less than a month after his election, the president-elect sent out a post-midnight tweet: ‘Just tried watching Saturday Night Live – unwatchable! Totally biased, not funny and the Baldwin impersonation just can’t get any worse. Sad.’ Getting madder, he accelerated his never-ending attempts to get even. His far-right appointments weren’t so much signs of his ideological commitment as symbols of his retribution.

Trump​ has thumped around Manhattan for an epoch like a dinosaur that survived extinction, anachronistic proof of Veblen’s late 19th-century Theory of the Leisure Class, an anthropological examination of the robber barons, published in 1899. Veblen described the tycoons flaunting their conspicuous consumption, their atavistic appropriation of feudal symbols suggesting pre-industrial rank, and their treatment of women as ‘trophies’ – an ‘archaic trait’ that ‘begins in the lower barbarian stages of culture’. The key to understanding these displays was that they established social status as based on the moguls’ distance from actual productive work.

If Trump was a ‘captain of industry’, a phrase Veblen popularised, then the industry was leisure: hotels, casinos, reality TV shows, a beauty pageant and a wrestling federation. More than a century after Veblen, the ultimate representative of the leisure class indulged in an aesthetic of ‘conspicuous waste’ in order to offer himself as an object of envy and magical thinking. ‘There has always been a display of wealth and always will be, until the depression comes, which it always does,’ Trump explained to Playboy. ‘And let me tell you, a display is a good thing. It shows people that you can be successful. It can show you a way of life.’ ‘Dynasty,’ he added, ‘did it on TV.’ It was conclusive proof.

Trump wanted his pretences to be accepted at face value as signs of his authenticity, his ostentation as accountability in lieu of tax returns. His recklessness was intended to engender deference, his disorder belief in his power to impose order. The faux aristocrat sought to inspire a faux populism: ‘I love the poorly educated.’ For Veblen, his vulgarity would have been self-defeating in the struggle for reputation, ‘the lower barbarian stages’, undermining any potential image of ‘honorific virtue’. In Veblen’s terms, he never learned to emulate the taste for understated pre-industrial trappings that would enable him to assimilate to the upper class.

His style has been unfailingly kitsch. His penthouse apartment at Trump Tower is museum-like in its curating of exquisitely tacky taste in a faux luxe style: marble floors, walls and columns; Louis XIV chairs with cushions stitched with the Trump coat of arms; gilded lamps, vases and crown mouldings; ceiling murals with scenes from Greek mythology (‘If this were on the ceiling of the Sistine Chapel,’ he boasted, ‘it would be very much in place in terms of quality’); a large copy of a statue of Eros and Psyche; a fake Renoir; coffee-table books, carefully placed – the ‘Vogue’ Living Book, the ‘Vanity Fair’ Oscar Night Book and a Muhammad Ali tribute book. ‘The Trump style is “developing-country despot”, rather than European or “evolved American”,’ Peter York wrote in the Times. ‘It doesn’t even try to get things “right” – “real” antiques, architecturally correct detailing or any of that – because, as with DC despots, neither the client nor the people he wants to impress care about that.’

Trump’s interest in interior decorating exceeds his interest in paintings. His major acquisitions have been a six-foot-tall portrait of himself done in five minutes by a little-known ‘speed painter’ and another portrait that now hangs over the bar at the Champions Bar and Grill at the Trump National Doral Miami Golf Resort. Both were bought with funds from the Donald J. Trump Foundation. Another portrait of himself in a golden glow as a young man in a tennis sweater hangs at his Mar-a-Lago mansion. He entitled it The Visionary.

He once turned down the chance of owning Andy Warhol’s pictures of Trump Tower. Warhol met the already famous Trump on 22 February 1981 at a birthday party for Roy Cohn. They met again on 24 April at Warhol’s Factory, where they discussed Trump Tower and agreed, Warhol noted in The Andy Warhol Diaries, that ‘I should do a portrait of the building that would hang over the entrance to the residential part.’ Warhol produced ‘a beautiful series of multi-layered paintings in black, silver and gold; some with a sprinkling of Warhol’s glittering diamond dust’, according to the Warhol Museum blog. Warhol’s rendering of Trump Tower was an idealised imagining. The two men met on 5 August at the Factory, where Trump delivered his judgment to the artist. ‘Mr Trump was very upset that it wasn’t colour co-ordinated,’ Warhol wrote. Trump sent his interior decorator ‘to come down with swatches of material so I can do the paintings to match the pinks and oranges. I think Trump’s sort of cheap, though, I get that feeling.’ In the end, Warhol couldn’t satisfy Trump and he never bought the paintings. Warhol’s 15 minutes with Trump were over. He ended up like the other stiffed contractors. They ran into each other once more on 26 February 1983 at another Roy Cohn birthday party. ‘And Ivana Trump was there and she came over and when she saw me she was embarrassed and she said: “Oh, whatever happened to those pictures?”’

‘It is a fact that my buildings are acclaimed and they have lasting power,’ Trump wrote in 2014 in an op-ed for the Chicago Tribune to tout his new Trump hotel in the city. At the press conference announcing that he would build Trump Tower, he said loudly to the architect, Der Scutt: ‘Give them the old Trump bullshit. Tell them it is going to be a million square feet, 68 storeys.’ Scutt replied: ‘I don’t lie, Donald.’ Trump’s aesthetic contribution to the design of his buildings has been to tell the architects to make them big and shiny. During the campaign he suggested he was an architectural genius. ‘Trump described himself as an Ayn Rand fan,’ an interviewer for USA Today reported. ‘He said of her novel The Fountainhead: “It relates to business [and] beauty [and] life and inner emotions. That book relates to … everything.” He identified with Howard Roark, the novel’s idealistic protagonist, who designs skyscrapers and rages against the establishment.’ Roark is an Ubermensch, a towering genius set above the mass of mediocrity. He blows up a building he has designed rather than submit to any modifications, is triumphantly acquitted after defending himself eloquently in court and wins the girl: it’s an adolescent boy’s dream plot, Nietzsche for teenagers. Trump’s description of the novel reveals no evidence that he has actually read it, but his identification with Roark is consistent with Rand’s exaltation of egoism.

Trump’s self-promotional grandiosity has prompted endless comparisons to P.T. Barnum, the showman and circus operator of the 19th century who was the son of a storekeeper. (A Google search turns up more than 520,000 references to ‘Trump Barnum’.) One of Trump’s advocates, also consumed by his own grandiosity, Newt Gingrich, raised the Barnum cliché in Trump’s defence: it ‘resonates well with the working class’, he said, ‘but not the elite’. The hackneyed comparison is demeaning to Barnum. Unlike Trump, who not only didn’t write the books that carry his name but doesn’t seem to have read them, Barnum wrote a great deal. He was witty; Mark Twain was an admirer. He was also a philanthropist, the founder of the Bridgeport Hospital, and an educator, helping to found and fund Tufts University. Both as a member of the Connecticut state legislature and as mayor of Bridgeport, he was responsible for a host of civic reforms and improvements.

Nobody in New York buys Trump’s humbug that he’s a reincarnation of the original rags-to-riches hero out of Horatio Alger’s Ragged Dick; or, Street Life in New York with the Boot Blacks, a Gilded Age tale of pluck and the Protestant Ethic that lifts an urchin to respectability through a business career and churchgoing. In a 1990 interview Trump boasted to Playboy that ‘the working man likes me because he knows I worked hard and didn’t inherit what I’ve built. Hey, I made it myself; I have a right to do what I want with it.’ Trump, the heir with the urchin’s manners, has undergone no moral transformation. The rapacious spirit of his formative Manhattan period – the world of The Bonfire of the Vanities, with its scandal-driven media, unscrupulous race hustlers and politically ambitious district attorneys – is still with him. But he also still lives in the shadow of the fictional character who became the symbol of the Roaring Twenties.

‘What preyed on Gatsby,’ the narrator asks himself in Fitzgerald’s novel, ‘what foul dust floated in the wake of his dreams?’ The fabulously wealthy Gatsby takes a mansion on Long Island, holds extravagant parties drawing the swells from Manhattan, and appears to be the effortless maestro of the scene. He has willed himself into being. Gatsby is actually Jay Gatz, a poor boy from the plains, in romantic pursuit of Daisy Buchanan, the upper-class object of his desire, who once rejected him. He believes he can win her back through displays of wealth and manners, but she is now married to Tom Buchanan, an upper-class boor. Trump’s claim to have risen Gatsby-like is the opposite of Gatsby’s magical self-invention. Gatsby was careful to maintain the air of the gentleman he wished to be taken for. Trump is the uncouth son of privilege for whom, as for Tom and Daisy, there are no consequences for ‘smashing things up’. Trump is Tom Buchanan farcically playing Gatsby. Gatsby might have appreciated the audacity, but would have avoided the shabbiness. Both Gatsby and Trump, however, are characters enthralled by the possibility of recapturing the past and reshaping it as they imagine it should have been.

What Gatsby and Trump also have in common are gangsters. Gatsby’s fortune is secretly derived from his bootlegging partnership with Meyer Wolfsheim, a character based on the mobster Arnold Rothstein, who fixed the 1919 World Series. Trump’s business has been dependent almost from the start on real-life racketeers. There was Anthony ‘Fat Tony’ Salerno, boss of the Genovese crime family, and Paul ‘Big Paulie’ Castellano, boss of the Gambino crime family, who owned the company that provided the ready-mix cement for Trump Tower, used in place of the usual steel girders. There was John Cody, the boss of Teamsters Local 282, who controlled the cement trucks and was an associate of the Gambino family. There was Daniel Sullivan, Trump’s labour ‘consultant’, who in partnership with the Philadelphia crime boss Nicodemos ‘Nicky’ Scarfo’s financier, sold Trump a property in Atlantic City that became his casino. There was Salvatore ‘Salvie’ Testa, ‘crown prince’ of the Philadelphia Mob, who sold Trump the site on which two construction firms owned by Scarfo built the Trump Plaza and Casino. There was Felix Sater, convicted money launderer for the Russian Mafia, Trump’s partner in building the Trump SoHo hotel through the Bayrock Group LLC, which by 2007 had more than $2 billion in Trump licensed projects and by 2014 was no more. There was Tevfik Arif, another Trump partner, Bayrock’s chairman, originally from Kazakhstan. Bayrock’s equity financing came from three Kazakh billionaires known as ‘the Trio’, who were reported to be engaged in racketeering, money laundering and other crimes. And so on.*

There was no art to these deals. Trump’s relationships with the Mob weren’t just about the quality of cement. In his defence it was said that doing business with the Mob was inescapable in New York, but the truth is that there were prominent developers who crusaded against the sorts of arrangement that Trump routinely made. From beginning to end, whether Cosa Nostra or the Russian Mafia, Trump has been married to the Mob.

On​ New Year’s Eve, President-elect Trump held a party at his Mar-a-Lago estate at Palm Beach for almost a thousand revellers from whom he cleared a neat profit. For members of his Mar-a-Lago Golf Resort, for which he levies a $100,000 entry fee, the price was $525 a ticket (guests at the hotel paid extra). For that they got to mingle with celebrities like Sylvester Stallone, who turned down Trump’s offer to become chairman of the National Endowment for the Arts, and Joe ‘Morning Joe’ Scarborough, the former Republican congressman turned TV talk show host. Marjorie Merriweather Post, heiress to the Post cereal fortune, collector of Russian art, Fabergé eggs and husbands, built the lavish 126-room estate in 1927. She left her art to the Hillwood Museum, which had been her Washington DC residence, the diamond earrings that had belonged to Marie Antoinette and other pieces of jewellery to the Smithsonian Institution, and Mar-a-Lago to the US government to serve as a winter White House. Trump snapped it up in 1985 when the government put the unused but costly property on the market.

As celebrants rang in the year in which Trump would become president, the man himself appeared on the stage of Mar-a-Lago’s gilded ballroom to tick off his future achievements: ‘We going to get rid of Obamacare!’ Standing next to him was a tuxedoed man pumping his fists at Trump’s every line to lead the cheering throng. Joseph ‘Joey No Socks’ Cinque is a former associate of the Gambino family boss John Gotti who was convicted in 1989 for possession of stolen artworks including a couple of $20,000 Chagall prints and a Miró. (The New York district attorney’s office withdrew a plea bargain after an informant reported a conversation in which Gotti was heard promising Cinque he would ‘take care of the DA’.) After getting involved in New York bars and clubs and the used-car business, Cinque got a new racket. Called the American Academy of Hospitality Sciences, it reportedly bestows Star Diamond awards on hotels and restaurants that pay its entry fee and annual charge. Half the trustees are Trump employees, including the general manager of his Bedminster, New Jersey golf club, the vice-president of his Mar-a-Lago resort, and his butler. Trump’s sons Donald Jr and Eric have been listed as ‘honorary trustees’, and Trump himself was ‘ambassador extraordinaire’. The Star Diamond website lists 19 Trump properties that receive its imprimatur. ‘How am I involved in it?’ Trump replied in 2015 to a reporter from Yahoo News. ‘I don’t know. I don’t know that my sons are involved with that, actually.’ Asked about Cinque, Trump said: ‘I don’t know him well. I don’t know him well, but I have found him over the years to be a very nice man.’ In 2014, Cinque’s website posted an article stating: ‘Joseph Cinque, president of the AAHS, has been attending Mr Trump’s party for the past 16 years. It is somewhat of a New Year’s Eve tradition for him and of course, he has become dear friends with the Trump family.’

More than the frolics at Gatsby’s mansion in West Egg, New Year’s Eve at Mar-a-Lago evokes the goings-on at another Long Island estate – that of the Corleone family. The founding father of what became the Trump Organisation, Frederick Trump, a German immigrant who changed his name from Drumpf, left a substantial legacy of New York real estate and investments that had originated in brothels and bars in the Yukon and the Pacific Northwest. When he died, his son Fred, then 15 years old, assumed his mantle under the stewardship of his mother. His housing business flourished from the 1930s until the early 1950s thanks to his close partnerships with the Brooklyn Democratic Party machine and a steady flow of loans from the Federal Housing Authority. In 1954, he was subpoenaed to appear before the Senate Banking Committee, where he was questioned about profit windfalls and inflated costs. From then on he would receive no FHA loans – which is the reason the Trump Village on Coney Island, among other projects, was greased by his Brooklyn political connections. Also cited in the FHA investigation was Fred Trump’s partner, contractor and financier William ‘Willie’ Tomasello, who according to the federal Organised Crime Task Force was associated with elements of both the Gambino and Genovese families.

Fred Trump appeared to be grooming Fred Jr to take over his business. But he was a harsh and exigent father and lost patience with his eldest son. Donald, though eight years younger, adopted his father’s attitude to Fred Jr. ‘Donald put Freddy down quite a bit,’ a family friend told the New York Times. ‘Donald was the child who would throw the cake at the birthday parties,’ Robert Trump, the youngest brother, who went to work for the Trump Organisation, reported to Vanity Fair. ‘If I built the bricks up, Donald would come along and glue them all together, and that would be the end of my bricks.’ Fred Jr rebelled, first by joining a Jewish fraternity at Lehigh University, and then by giving up on the Trump business and becoming an airline pilot. He literally flew away. But the free spirit of the Trump family fell into alcoholism, crawled back to work on one of his father’s construction crews and died in 1981 at the age of 43. When Fred Trump died in 1999, his will completely cut out Fred Jr’s children. They sued for their share, claiming that the will had been written under ‘undue influence’ from Donald Trump. In retaliation, Donald withdrew payments for the medical care of Fred III, who had cerebral palsy. After extended litigation, a settlement was reached. Donald had learned some lessons from Fred Jr’s demise. ‘Our family environment, the competitiveness, was a negative for Fred,’ he told Playboy.

It wasn’t easy for him being cast in a very tough environment, and I think it played havoc on him … He was the first Trump boy out there, and I subconsciously watched his moves. I saw people really taking advantage of Fred and the lesson I learned was always to keep up my guard 100 per cent, whereas he didn’t. He didn’t feel that there was really reason for that, which is a fatal mistake in life. People are too trusting.

While the Trump money had its origins in prostitution and multiplied through ties to clubhouse politics and Mob figures, neither Frederick Trump nor Fred Trump fits the role of Don Vito Corleone. Vito Corleone avoided flamboyance and publicity. He was straitlaced, patient and tactful. He gained power and influence not only through crime and corruption but also by understanding people’s feelings and helping them when they were in trouble. The Don’s bond was not the Trump way.

Fred Jr resembled the middle Corleone brother, Fredo, who is weak and indecisive, and is eventually murdered by his younger brother, Michael, after he assumes control of the family business. Donald was most like the hot-headed Santino ‘Sonny’ Corleone, whose impulsiveness results in his assassination by rival gang members at a tollbooth. Donald has raced through many tollbooths, but has survived the hail of gunfire. Though he grabbed hold of the family business, he is not much like Michael Corleone, a war hero, Dartmouth graduate and tragic figure who initially resists the poisoned Corleone chalice. Early on, he tells his Wasp wife he has nothing to do with the sordid business: ‘That’s my family, Kay – that’s not me.’ But he becomes everything he was determined not to be. His success is to have transformed the Family into a corporation. ‘This is the business we have chosen,’ he is told by Hyman Roth, the Mafia character based on the real-life mob financier Meyer Lansky. Roth also speaks about the scale of the enterprise, ‘bigger than US Steel’, and suggests to Michael that someday he might be able to choose a president.

The member of the Trump family who most resembles Michael Corleone is Ivanka. Her father’s favourite, the ambitious and fashionable Manhattanite presents herself as an advocate of childcare and climate change policies, selling herself as the one hope for decency among the Trumps. While merchandising her dresses, shoes and jewellery she has achieved a degree of social acceptance in the city. She represents Donald’s last chance at respectability, but her precarious image depends finally on repudiation of the father she worships. ‘That’s my family – that’s not me.’

Roy Cohn​ , the Mafia lawyer, was more than just the consigliere in Trump’s story. He was Donald’s mentor, his godfather. If Trump received an education beyond his two years at Fordham and as a transfer student at Wharton (‘I’m a smart person. I went to the Wharton School of Finance’), it was from his guide through the circles of the Inferno, who conducted masterclasses in malice. Trump was an apt pupil in aggression. ‘I don’t think I got that from Roy at all,’ Trump told the Washington Post. ‘I think I’ve had a natural instinct for that.’ He didn’t really need an education in heartlessness, but he learned the finer points from Cohn. Offering his highest praise, Trump called him ‘a total genius … he brutalised for you.’

Like Trump, Roy Cohn was the pampered son of a politically connected New York family. His father, Albert Cohn, was a major player in the Bronx Democratic Party, an assistant district attorney who was appointed to the division of the New York Supreme Court presiding over the Bronx. Roy Cohn was a child prodigy; he graduated from Columbia Law School at the age of twenty, and was appointed as an assistant US attorney for the Southern District of New York. He promoted himself in his early cases by giving false leaks to the New York World Telegram. He was put in charge of prosecuting communist agents, staging several prominent show trials, including one of 11 Communist Party officials for subversion. In 1951, he took effective control of the trial of Julius and Ethel Rosenberg, who were accused of stealing atomic secrets. He pulled strings to appoint both chief prosecutor and judge, then urged the judge to impose the death penalty, though the evidence against Ethel Rosenberg was flimsy. Cohn’s tour de force brought him to the attention of Senator Joseph McCarthy, who hired him as chief counsel in his Red-hunting investigations. After the Red Scare came the Lavender Scare, when Cohn launched a campaign against homosexuals in government jobs, though he was a closeted homosexual himself.

Cohn opened a law office in New York, taking on such clients as the Mafia kingpins Tony Salerno, Paul Castellano, John Gotti and Carmine ‘The Cigar’ Galante, underboss of the Bonanno crime family – as well as the Catholic Archdiocese of New York and the New York Yankees. He was the city’s supreme fixer. The menacing milieu around him was portrayed in the 1957 noir movie Sweet Smell of Success, about an influential and vicious New York tabloid newspaper columnist called J.J. Hunsecker, modelled on the latter-day Walter Winchell, who operates from a booth at the 21 Club, where he dines with movers and shakers. Hunsecker rules the town, making and wrecking reputations through smears and fear. When he uses a PR agent to destroy his sister’s jazz musician boyfriend, who denounced him for his ‘phony patriotism’, the plot turns nasty.

Donald Trump met Roy Cohn at Le Club, a private New York disco, in 1973, when Trump was 27 and had a serious problem. The Justice Department was suing him and his father for racial discrimination in their building at 100 Central Park South. ‘My view is tell them to go to hell,’ Cohn advised, ‘and fight the thing in court.’ From that moment, Cohn and Trump were inseparable. Cohn recalled that Trump would phone him more than a dozen times a day. With Cohn as their attorney the Trumps filed a countersuit against the federal government for using ‘Gestapo-like tactics’. Their suit was instantly dismissed and two years later the Trumps settled after being forced to sign a decree forbidding them from engaging in discriminatory practices.

Roger Stone, a longtime Cohn protégé who began his political career as a dirty trickster and ‘ratfucker’ for Richard Nixon’s re-election campaign in 1972, explained the relationship. ‘First of all,’ he told an interviewer, ‘Roy would literally call up and dictate pieces for Page Six [of the New York Post] because Rupert [Murdoch] was a client and because Roy always had good material. So Roy understood the tabloids. Donald, I think, learned the tabloid media, and the media cycle, from Roy.’ Cohn was the sorcerer and Trump the apprentice. ‘Roy was a mentor in terms of the fast track,’ Stone said. ‘I mean, Donald was from Queens, Manhattan’s the fast track. I think, to a certain extent, Donald learned how the world worked from Roy, who was not only a brilliant lawyer, but a brilliant strategist who understood the political system and how to play it like a violin.’ For Trump, Cohn served ‘like a cultural guide to Manhattan’, Stone told the Washington Post. ‘Roy was more than his personal lawyer.’

Cohn took him to the 21 Club, where they held court in Cohn’s reserved red leather booth. He took him to his townhouse on 68th Street, where he lived and conducted his law business, and which was filled with a running crew of attractive young gay men, models, cigar-chomping politicians, gangsters and journalist hangers-on. ‘Roy lived in a matrix of crime and unethical conduct,’ according to his biographer Nicholas von Hoffman. He ‘derived a significant part of his income from illegal or unethical schemes and conspiracies, the most blatant of which was not paying income tax’.

Cohn initiated Trump into the highlife and lowdown at the hottest club in town, Studio 54. ‘What went on in Studio 54 will never, ever happen again,’ Trump told a journalist much later.

First of all, you didn’t have Aids. You didn’t have the problems you do have now. I saw things happening there that to this day I have never seen again. I would watch supermodels getting screwed, well-known supermodels getting screwed on a bench in the middle of the room. There were seven of them and each one was getting screwed by a different guy. This was in the middle of the room. Stuff that couldn’t happen today because of problems of death.

Cohn greased the skids with favours. ‘I got to know everybody,’ Trump said. Cohn arranged for the Mob to construct Trump’s towers and provide protection against labour trouble. ‘You know how many lawyers in New York represent organised-crime figures? Does that mean we’re not supposed to use them?’ Trump asked. Cohn threatened to sue anyone in Trump’s way to secure leases on properties and city tax abatements. He wrote the prenuptial agreement stipulating that Trump’s first wife, Ivana, would return all gifts in the event of a divorce, and coerced her to sign; Cohn had suggested an associate to serve as her lawyer. (‘I would never buy Ivana any decent jewels or pictures. Why give her negotiable assets?’ Trump told his friends, according to Vanity Fair.) And Cohn finagled a federal judgeship for Trump’s sister, Maryanne Trump Barry. When anyone resisted Trump’s demands, he waved Cohn’s picture in their face. ‘Would you rather deal with him?’ he would say.

The State of New York disbarred Cohn in 1986 for unethical and unprofessional behaviour described in the judgment as ‘particularly reprehensible’. A month later, he died of Aids, an illness he tried to conceal (he told Trump he had cancer). He was an outrageous racist and self-loathing Jew, freely spewing epithets about ‘niggers’ and ‘kikes’. He was also a self-hating homosexual, who obsessively denounced ‘fags’ and crusaded against gay rights. When he was dying Trump turned away from him, shifting his business to other lawyers. ‘I can’t believe he’s doing this to me,’ Cohn said. ‘Donald pisses ice water.’ Cohn called Trump to ask him to find a room in one of his hotels for Cohn’s former lover and assistant, near death himself from Aids. Trump got him a ‘tacky’ room and sent Cohn the bills. Cohn refused to pay. Trump’s underlings called to evict the dying man. The only surprising part of the story is Cohn’s shock.

Cohn made an afterlife appearance as a major character in Tony Kushner’s Angels in America: A Gay Fantasia on National Themes, staged in 1993 and produced as a TV miniseries in 2003. Dying of Aids and disbarred, Cohn denies his homosexuality, attempts to hoard an experimental drug, and finds himself in a hospital bed cared for by a nurse who is a drag queen. Ethel Rosenberg hovers as a ghost to haunt him and in his death scene chants the Kaddish as an act of mercy over his unrepentant soul.

At the height​ of the Cold War, Richard Condon’s The Manchurian Candidate laid out a Russian conspiracy to elect a malleable president. Raymond Shaw, a US army sergeant during the Korean War, is captured and brainwashed along with the other members of his unit in Manchuria. His comrades are programmed to testify falsely to his bravery, for which he wins the Congressional Medal of Honor. ‘Raymond Shaw is the kindest, warmest, bravest, most wonderful human being I’ve ever known in my life,’ they all declare. The American war hero is turned into a Russian sleeper agent, groomed to assassinate the presidential nominee at the convention. But Major Ben Marco, a former member of his army unit, breaks through his brainwashing and so instead of murdering the nominee, Shaw shoots his mother, who had been controlling him throughout, along with his idiotic stepfather. Decades later, Condon explained the inspiration for the perverse dynamic between Raymond Shaw and his mother. ‘Raymond’s mother is Roy Cohn, and her husband Johnny is McCarthy. I was fascinated by the very strange relationship between Cohn and the senator. Roy ran McCarthy, totally dominated him.’

What Cohn would have made of Donald Trump’s romance with Vladimir Putin is anybody’s guess. The Red-hunter might have been appalled at his client becoming an agent of influence for the former agent of the KGB. But Cohn might have approved. After he departed, Trump fell and rose, his resurrection partly financed by clandestine loans from Russian banks linked to a state governed on Mafia principles. During the 2016 campaign, Putin appears to have provided assistance to Trump through the Russian intelligence services’ hacking of the Democratic National Committee and the Clinton campaign, and his political model may serve as something of an inspiration too. Trump’s business has always operated organisationally like a prototypical Mafia, with a tight circle of family, friends and flunkies, bearing little resemblance to a modern corporation. As Masha Gessen put it in the New York Review of Books, borrowing from the Hungarian sociologist Bálint Magyar, the ‘post-communist mafia state’ is ‘run like a family by a patriarch who distributes money, power and favours’. Usually, the ‘family’ is ‘built on loyalty, not blood relations, but Trump is bringing his literal family into the White House. By inviting a few hand-picked people into the areas that interest him personally, he may be creating a mafia state within a state.’ He has long been attracted to authoritarianism. In his 1990 interview with Playboy he expressed admiration for the Chinese government’s violent repression of the democracy movement. ‘When the students poured into Tiananmen Square, the Chinese government almost blew it,’ he said. ‘Then they were vicious, they were horrible, but they put it down with strength. That shows you the power of strength. Our country is right now perceived as weak … as being spat on by the rest of the world.’

Talk of a ‘mafia state’ echoes another period’s fears of fascism. In 1935, fascist figures emerged not just in Europe but in America. Father Charles Coughlin held millions of his radio flock in thrall with jeremiads against bankers, liberals and Jews, and enlisted them into his Union for Social Justice. The DuPonts and other wealthy conservatives financed the American Liberty League to campaign against the New Deal as un-American, spending twice as much as the Republican Party. William Randolph Hearst likened Roosevelt to Karl Marx – ‘imported, autocratic, Asiatic’ – and declared: ‘Whenever you hear a prominent American called a “Fascist”, you can usually make up your mind that the man is simply a loyal citizen who stands for Americanism.’

It was in this combustible environment that the most celebrated writer of the day, Sinclair Lewis, the first American writer to win the Nobel Prize, voiced his sense of imminent catastrophe in the American heartland. Lewis’s previous novels – Main Street, Babbitt, Elmer Gantry and Arrowsmith – had satirised the hypocritical manners and morals of small-town life. He punctured the suffocating prejudices, mean-spiritedness and crushed idealism in the nativist, isolationist and Prohibitionist America of the Republican-dominated 1920s. His characters were studies in the cultural constraints of the age. There was not a Gatsby among them. Now, his alternative history showed how the people of Main Street might fare in the face of homegrown fascism. In It Can’t Happen Here, it happened here.

FDR loses re-election in 1936, defeated by Senator Berzelius ‘Buzz’ Windrip, ‘a Professional Common Man’, who pledges a return to ‘founding’ principles. He embodies ‘every prejudice and aspiration of every American Common Man … the Common Man twenty-times magnified by his oratory, so that while the other Commoners could understand his every purpose, which was exactly the same as their own, they saw him towering among them, and they raised hands to him in worship.’ A tabloid journalist, Lee Sarason, generates a blizzard of propaganda and ghostwrites Windrip’s manifesto, Zero Hour: Over the Top, excerpts from which appear as chapter epigraphs. ‘In the little towns, ah, there is the abiding peace that I love, and that can never be disturbed by even the noisiest Smart Alecks from these haughty megalopolises like Washington, New York, & etc.’ ‘Sarason had encouraged Windrip to keep up in the Great World all of the clownishness which … had endeared him to his simple-hearted constituents.’ A radio preacher deploys his League of Forgotten Men behind Windrip. Among Windrip’s ‘camp followers’ are ‘Intellectuals and Reformers and even Rugged Individualists, who saw in Windrip, for all his clownish swindlerism, a free vigour which promised a rejuvenation of the crippled and senile capitalistic system’. President Windrip announces a new ‘Corporatist’ state, suspends civil liberties and sends his militia, the Minute Men, to enforce order. Sarason directs propaganda, telling the masses ‘they were the honoured foundation stones of a new Civilisation … And they had the Jews and the Negroes to look down on, more and more … Every man is a king so long as he has someone to look down on.’ Windrip’s policies fail to deliver on his extravagant promises. Dissidents disappear into concentration camps. A New Underground organises against the regime. Sarason stages a coup and installs himself as president. Then his ally, General Dewey Haik, ousts him and invades Mexico to arouse patriotic unity. The country descends into civil war. The end.

The Confidence Man: His Masquerade was the last full-length book Herman Melville published in his lifetime. Moby-Dick had been poorly received and Melville could no longer scrape by on his writing. A flat-out failure, he was about to take a job as a clerk in the New York Customs House. His new book, inspired by a story he read in a newspaper, takes place on April Fool’s Day, when a mysterious stranger boards a Mississippi steamboat named the Fidèle. We are a long way from the Pequod. The confidence man is anything but loyal. He assumes different guises as he works his way through the passengers, from the ‘cosmopolitan’ to the kindly old lady. To one he sells non-existent shares in the Black Rapids Coal Company. He inveigles funds for the imaginary Seminole Widow and Orphan Asylum. He hits up others for something he calls ‘the World’s Charity’. From yet another he coaxes money for an investment in ‘a Protean easy chair for invalids’. Whenever any of his dupes baulks he appeals to their sense of confidence, understanding that their weakness is their desire for hope. Written at the nadir of his own hope, Melville masked his bitterness with satirical humour. The reviews of his plotless and oblique work were unkind. He withdrew into the Customs House. In The Raven and the Whale, the critic Perry Miller wrote: ‘The few contemporaries who examined the book were in no position to see it as, whatever else it is, a long farewell to national greatness.’ The only character who escapes the confidence man’s swindle, the only one to lack confidence, is the steamboat’s barber, who refuses to wield his scissors without first being paid, and has hung a large sign in his shop reading: ‘NO TRUST.’