21. Sometimes winning means not losing now.
It’s how he (with the help of Roy Cohn) “won” the federal government’s suit in the 1970s against him and his father for racist rental practices at the apartments they owned:
The accepted narrative of this case is that Trump and his father lost. The Justice Department did indeed notch what it considered a victory—a consent decree mandated that the company rent to more tenants who weren’t white. But looked at slightly differently, it was every bit a triumph for Trump, too. Typically seen as a not-quite-two-year episode more or less confined to the mid-’70s, the saga actually lasted for almost a decade. The government ascertained quickly that the Trumps had failed to adhere to the terms of the decree and apparently had little intention of ever complying. A revolving-door roster of exasperated prosecutors, stymied by Cohn’s shameless, time-buying tactics, found it practically impossible to enforce the specifics of their “win.” And Trump simply waited them out. He emerged in Manhattan, his reputation virtually unscathed, to wrest unparalleled public subsidies to convert the collapsing Commodore Hotel into the glossy Grand Hyatt and then pry additional tax cuts to erect Trump Tower—the one-two punch of projects that constituted rocket propellant for Trump’s entire adult existence. His monetary wealth. His life-force celebrity. His extraordinary presidency.
“He’s used litigation historically,” O’Brien told me, “to keep hostile forces at bay and to delay reckonings.”
22. Sometimes winning is just winning that hasn’t happened yet.
It’s how he’s used the word “comeback” over the years. “If there’s a moment that you’re not quite a winner, you’re almost a winner. You’re practically a winner,” Blair explained. “It’s a cloak that contains winning as a part of it.”
23. And sometimes winning is whining.
“By claiming victory over and over again, it starts to become a self-fulfilling prophecy,” Trump biographer Harry Hurt III told me.
He believes, because of Norman Vincent Peale, that simple assertion can lead to actual achievement.
“I win, I win, I always win,” he said in 2005. And when he doesn’t? “I keep whining and whining until I win.”
“He’s the most successful failer of all time,” I once wrote.
24. Reality doesn’t matter.
He just rewrites (and prewrites) his own history:
He is who he is, is where he is, is seen the way he’s seen by so many, because of it. He’s self-made! (He’s not.) He’s a businessman with a Midas touch. (He’s not.) He’s an outsider! (He was an insider—thanks to his father’s political connections—the day he was born.)https://7c7899e8400d5f44afdcfc0a4c4777f9.safeframe.googlesyndication.com/safeframe/1-0-37/html/container.html
“He’s been able to create his own reality,” late Trump biographer Wayne Barrett once told me.
“He can build 200 yards of wall and say he built the wall,” old Upper West Side Trump foe Steve Robinson told me. “And the press, which has been so diligent in fact-checking, will say, ‘No, no, no, wait a second, Mr. President. You didn’t build the wall that you said you were going to build. You only built 200 yards of it.’ And it won’t matter.”
25. The past doesn’t matter.
Never has. Not to him:
Trump, according to those who know him best, is not a man given to backward looks—“the most present human being I ever met,” in the words of an intimate. Traditionally, Trump has seen the past as something to be either razed or twisted for expediency.
“Trump has about as much interest in history as he does in literature and philosophy,” O’Brien told me. “Which is to say almost nonexistent.”
26. The future doesn’t matter.
He is the “episodic man.”
27. Nothing, actually, matters.
Whatever happens, happens,” he says.
“I’m very much a fatalist,” he says.
“He’s empowered to be a fatalist,” O’Brien told me, “because he’s been insulated from his failures by wealth, privilege and celebrity—so the impact of catastrophes is more muted in his world than it is in the world of an average person.”
28. Create your own world.
It helps explain his complicated relationship with New York:
For Trump, as inhospitable as he found the city on the street, the parlors of high society were equally problematic—and he created a refuge. It was some 600 feet in the sky, where the faucets were gold, the baseboards were onyx and the paintings on the ceiling, he would claim, were comparable to the work of Michelangelo in the Sistine Chapel. At the top of Trump Tower, biographer Tim O’Brien told me, he could live “at a remove from the city and its amazing bloodstream of ideas and people and culture”—“encased,” added fellow biographer Gwenda Blair, “within this bubble of serenity and privilege.”
“I am the creator of my own comic book,” he once said, “and I love living in it.”
29. Tell your own story.
He started telling his early on:
Trump was, and still is, they say, a confident, competitive, aggressive, impulsive, zero-sum, win-at-all-costs, transactional, unpredictable, often underinformed and ill-prepared, gut-following, ego-driven, want-it-and-want-it-now negotiator. His self-burnished image as a tip-top deal-maker long has obscured an actual record that is far more mixed, pocked with moves and acquisitions that scratched a passing itch but created massive financial problems later. His best work, too, was his earliest work. Trump was at his most patient, his most diligent, his most attentive and his most creative—his most effective—some 35 to 45 years ago, when he was intent on pile-driving into the cultural bedrock powerful storylines on which he would build his career as a celebrity business tycoon
“Americans are suckers for a good story,” Sheinkopf told me. “Donald Trump is going to give ’em a good story.”
“Donald Trump is an excellent storyteller. It’s like we’re all amazed by his ability to cast himself in the best light possible. And that’s kind of what campaigning is,” Amanda Carpenter, a former speechwriter for Ted Cruz and the author of Gaslighting America: Why We Love It When Trump Lies to Us, told me. “He just does it with staggering audacity.”
30. Shame is for losers.
“He’s not feeling ashamed,” Res once told me. “He’s feeling aggrieved.”
31. There is no subtext.
And there is no filter.
He thinks it, he says it.
He thinks it, he tweets it.
32. Everything’s a transaction.
“Donald Trump,” Barrett wrote, in January of 1979, “is a user of other users.”
“As a contributor,” Trump told POLITICO in a statement in the summer 2015, referring to checks he’s written to [Hillary Clinton’s] campaigns as well as the Clintons’ foundation and Bill and Hillary Clinton’s attendance at his third wedding, “I demanded that they be there—they had no choice and that’s what’s wrong with our country. Our country is run by and for donors, special interests and lobbyists, and that is not a good formula for our country’s success. With me, there are no lobbyists and special interests. My only special interest is the United States of America.”
33. Nothing’s on the level.
Trump was “schooled and shaped by some of the most committed, effective and objectionable practitioners of quid pro quo.”
34. The ends justify the means.
“He stands for what he can get away with,” D’Antonio, the biographer, told me. “Looking for the loophole, pushing it as wide as possible, going through it,” Blair added. “There’s a certain American romance to getting away with it,” said Jim Zirin, a former federal prosecutorand the author of the book Plaintiff in Chief: A Portrait of Donald Trump in 3,500 Lawsuits.https://7c7899e8400d5f44afdcfc0a4c4777f9.safeframe.googlesyndication.com/safeframe/1-0-37/html/container.html
“What he does, he has been successful at,” said Sexton. “It’s important to recognize that, or you go into the next discussion overconfident, thinking that he couldn’t possibly pull this crap off. And you wake up six months later, look around, and wonder, ‘How the hell did he pull that crap off?’ And that’s a real danger. And it keeps happening.”
“Imagine if Roy Cohn were president,” Marty London, one of the lawyers who worked on Cohn’s disbarment, told me. “That’s basically what we have now. We have a Roy Cohn as president. He has no morals. There are no boundaries. He does what he wants.”
35. You can’t be stopped if nobody stops you.
Over and over it’s been true for Trump:
Whether Trump could remain not only financially solvent but reputationally intact was an open question for the entirety of the first half of the 1990s. So many times, he could have been snuffed, stopped, rendered a relative footnote, his place in the history of this country limited to status as a gauche totem of a regrettable epoch of greed. That, needless to say, is not how the tale played out. Trump is many things. A developer. A promoter. A master media manipulator. A grown-old rich kid. The president of the United States. Above all else, though, he is a survivor.
“The ultimate survivor,” former Trump casino executive Jack O’Donnell told me recently.
But it’s not just that Trump has survived that’s important to consider at this moment—it’s how he has done it. Armed with extraordinary audacity, constitutional sangfroid, a stomach for tumult, an acumen for recasting obvious losses into strange sorts of wins, and the prodigious safety net bequeathed by his wealthy, wily father, he has plowed past myriad hazards. And he did it by tying himself tightly to his bankers and lenders in New York and to gaming industry regulators in New Jersey—who let him live large until they couldn’t let him die without fatally wounding themselves. He effectively inhabited hosts, using them to get bigger and bigger in the ’80s until he was practically perversely invincible.https://7c7899e8400d5f44afdcfc0a4c4777f9.safeframe.googlesyndication.com/safeframe/1-0-37/html/container.html
“He’s a magician that way,” said Jennifer Mercieca, a professor at Texas A&M University and the author of a book about Trump’s rhetoric, Demagogue for President. “Other people would stop and recognize that they were defeated. Or that they should be shamed. He refuses.”
“He thinks he’s immune to everything,” O’Brien said. “Always did,” said Res.
36. People aren’t inherently good.
“Man is the most vicious of all animals,” Trump told People in 1981.
“Never make people your heroes,” Nunberg told me when I asked what he’d learned from Trump.
37. People look out for themselves.
“He figures it out,” Blair told me, “so that for people to go against him, it’s going to make them look bad.”
38. People don’t change.
“Can the leopard change its spots?” Blair asked. “The tiger its stripes?”
Trump has managed in the Oval Office in Washington pretty much exactly the way he managed on Fifth Avenue in New York, say people who worked for him at different points over the past 45 years as well as writers of the best, most thoroughly reported Trump biographies. In recent interviews, they recounted a shrewd, slipshod, charming, vengeful, thin-skinned, belligerent, hard-charging manager who was an impulsive hirer and a reluctant firer and surrounded himself with a small cadre of ardent loyalists; who solicited their advice but almost always ultimately went with his gut and did what he wanted; who kept his door open and expected others to do the same not because of a desire for transparency but due to his own insecurities and distrusting disposition; and who fostered a frenetic, internally competitive, around-the-clock, stressful, wearying work environment in which he was a demanding, disorienting mixture of hands-on and hands-off—a hesitant delegator and an intermittent micromanager who favored fast-twitch wins over long-term follow-through, promotion over process and intuition over deliberation.
39. You are who you are.
“He’s the same Donald Trump as the Donald Trump I knew when I was working with him,” former Trump Organization executive vice president Louise Sunshine, who worked for Trump for 15 years starting in the early ’70s, told me.
“Same guy we’ve known for the last 20 years,” O’Brien said. “Donald being Donald,” said former Trump publicist Alan Marcus. “He’s never going to evolve in how he does things and runs things,” a former employee said. “Because that’s what got him to the Oval Office.”
“People,” Nunberg told me, “knew who they were electing, right?”
40. No slight is too small.
“As long as I’ve known him, he has never been able to take criticism of any kind,” said Nobles, the former Trump Shuttle president. “You’d think at this point you’d be able to roll with the punches. But he never has.”
41. Never turn the other cheek.
“Get even!”
“… as viciously and violently as you can.”
42. Nothing worse than weakness.
“Weakness,” Tony Schwartz, the co-writer of The Art of the Deal, told me, “is Trump’s greatest fear.” He can’t show it.
43. The loneliness is bottomless.
The middle son of a stony, workaholic father with whom he had an “almost businesslike” relationship, Trump is a double divorcee, a boss with a professed distaste for having partners or shareholders, a television-tethered, hamburger-eating homebody and a germaphobe who has described shaking hands as “terrible,” “barbaric” and “one of the curses of American society.” He’s been a loner most of his life. At New York Military Academy, everybody knew him but few of his fellow cadets knew him well. In college, he made no friends he kept. After he moved to Manhattan, he lived in a sealed-off triplex penthouse, relied on a small, family-first cadre of loyalists and mainly made more enemies than allies (the mayor was a “moron,” elite “so-called social scene” types were “extremely unattractive people,” and on and on). At his casinos in Atlantic City, he was adamant about not mingling with the gambling masses. Now, in Washington, he’s a two-scoops cable-watcher inside the White House when he’s not weekending at his clutch of protective, name-branded bubbles. Trump, forever, has collected an array of acquaintances, fellow celebrities and photo op props, while friendships mostly have been interchangeable, temporary and transactional.
“He was and is a lonely man,” O’Donnell told me.
“One of the loneliest people I’ve ever met,” O’Brien told me.
44. Everybody needs to be seen.
It’s something I wrote in 2016:
Trump has tried his whole life to address the lack of love he felt as a boy by attracting as much attention as he could as a man. … Trump is an addict. Not of substances. He’s a teetotaler. And he has said he’s never done drugs. “But his drug is himself,” one of his former campaign advisers told me this past weekend. He has put himself on display his entire adult life. He was never some mysterious titan of industry pulling hidden levers of power inside secluded mansions. He has always wanted to be seen, and seen and seen and seen …
It’s something I wrote in 2020: “Donald Trump is the damaged product of an absent mother and a sociopathic father.”
“A black hole of need,” in the words of Mary Trump.
45. Nothing’s ever over.
“He’s always going to have something,” Blair said, “to make you tune in again.”
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