How Trump Decides Who Deserves Loyalty — And Who Gets Fired

The billionaire seems eager to pitch himself as the world's most loyal boss. The reality is slightly more complicated.

For a man who once tried to trademark the phrase "You're fired," Donald Trump seems awfully eager these days to cast himself as a loyal boss.

With his campaign reeling from tactical blunders and his inner circle gripped by infighting, the billionaire has spent weeks defiantly rejecting calls to fire his embattled campaign manager, Corey Lewandowski — and, often in the same breath, touting that decision as proof of his own personal character.

"Folks, look, I'm a loyal person," Trump said last month in a CNN town hall after Lewandowski was arrested for allegedly grabbing a female reporter. "It would be so easy for me to terminate this man, ruin his life, ruin his family.”

If the talking point originated as damage control, Trump quickly transformed it into a proactive pitch for his candidacy. Before long he was bringing up l'affaire Lewandowski unprompted at his rallies, and seizing the chance to spin it whenever the subject came up in interviews.

"I will be very loyal to the country," he said on Face the Nation.

"I will be loyal to Wisconsin," he proclaimed in Milwaukee.

During a meeting with Jewish activists and reporters this week in New York, Lewandowski informed Trump that the charges had been dropped. “Oh, good,” the candidate reportedly responded. “Now tell my friends from, in some cases, Israel, how loyal was Mr. Trump to you?”

“More than I could possibly fathom,” Lewandowski replied. “I am so grateful.”

This narrative has taken hold among Trump's aides, fans, and Twitter followers, who deploy it with the reverence of a mob family describing the code of omertà. As Lewandowski recently put it to New York Magazine, "This campaign, above all other things, is about loyalty."

But if a bone-deep belief in personal loyalty really is the guiding principle in Trump's decision-making, it hasn't always been that way. A review of the billionaire's tumultuous, decades-long career — including interviews with former employees, aides, and confidantes — suggests that Trump's dedication to even his closest allies can wear thin, particularly at moments of professional crisis. Far from a tight-knit family of blood brothers, The Donald's inner circle has been purged and repopulated many times over the years. Devoted workaholics burn out and flame out. Longtime alliances end with lawsuits and tabloid sniping. Sometimes reconciliation follows, sometimes grudges endure — and rarely does Trump refuse to bury the hatchet when it's good for the bottom line.

A presidential campaign isn't real estate or reality TV, but the attention on Trump — and the expectations for him to perform — have never been more intense. As the Republican frontrunner scrambles to beat back a late surge from the GOP's anti-Trump forces amid an escalating power struggle inside his own campaign, the coming months will no doubt be chaotic and unpredictable for Trump and his team. Who will get his loyalty, and who will get kicked to the curb?

You don’t have to reach too far back for an example of Trump abandoning a faithful staffer. Just last summer, his nascent campaign fired Sam Nunberg — a young New York operative who had spent years working as Trump’s political adviser — after Business Insider published old racist Facebook posts he had written.

In a recent interview, Nunberg said he pleaded with his boss not to fire him. Trump had actually cut him loose once before, in 2014, after Nunberg arranged for him to be interviewed by BuzzFeed News, and the resulting profile displeased the billionaire. In that case, Nunberg said, he had chosen to "fall on his sword" to help Trump save face — and he was rehired the next year. This time, he believed Lewandowski had personally leaked the Facebook posts in an effort to oust him. (The campaign did not respond to requests for comment, but Lewandowski has denied this.)

Nunberg now notes that even though Al Sharpton found it in his heart to forgive him for the racist posts, his longtime boss was less generous. And while he ultimately accepted Trump's decision, Nunberg was hurt when the campaign announced his termination with a press release that called him a "low-level, part-time consultant."

“Why would Trump even approve that statement?” Nunberg asked, eight months later.

As for Trump’s decision to stand by his current campaign manager amid a much greater public backlash, Nunberg is skeptical that the decision was motivated solely by principle.

“It seems to me it’s a convenient argument,” he said. “Donald is very superstitious, and I can see him [saying], ‘I’m winning with this guy, I don’t give a shit.’ [Trump] can certainly be loyal, but it’s selective.”

Of course, not every lieutenant who makes it to the inner sanctum of Trump Tower gets so unceremoniously defenestrated. Some key aides, in fact, never lose their perch. Keith Schiller, a retired NYPD detective who runs security for Trump, has held the job for 17 years. Rhona Graff, Trump's longtime secretary and gatekeeper, has been with him for more than 25 years. In private and in public, both of them gush about their boss's generosity and extol his virtues with what seems like genuine affection.

In other cases, Trump has shown a tendency to toss aside top employees — even those who share his DNA — when he's under extreme pressure (or, perhaps, looking for a scapegoat). In 1990, when the disastrous opening of the Taj Mahal Casino threatened to unravel Trump's Atlantic City casino empire, he aimed his fury at his younger brother, Robert, who worked on the project. According to a 1991 book written by a former Trump executive, the magnate angrily berated Robert in front of other employees.

“I thought you could handle this,” Trump said. “I must’ve been out of my mind. I let you make recommendations. I’m sick and fucking tired of listening to you.”

Robert immediately departed the casino seething, according to the book, saying, “I don’t need this.”

Trump’s critics said he was trying to throw his brother under the bus to cover up for his own failures. True or not, the episode reportedly put a lasting strain on their relationship.

“I think that he showed some disloyalty when he blamed his brother and the managers over at the casinos for the problems with the casinos,” said Barbara Res, a former executive in the Trump Organization. But, she reasoned, Trump's company was on the brink of bankruptcy and his financial problems were spiraling. "He was not himself.”

At the same time Trump's business was tanking, the tawdry details of his breakup with his first wife, Ivana, were being smeared across the New York tabloids. Charged with the unenviable task of preserving the celebrity businessman’s image was Howard Rubenstein, a veteran PR man who had worked for Donald for 17 years, and before that represented his father, Fred Trump.

Rubenstein's talents were legendary — Rudy Giuliani later hailed him as “the dean of damage control” — but tamping down coverage of a juicy celebrity divorce proved all but impossible. Incensed by the nasty headlines that were piling up, Trump abruptly axed his longtime publicist one day, giving notice of the decision in what USA Today called a “curt letter.”

“There was a time when he was upset with everybody,” Rubenstein told BuzzFeed News more than two decades later. Still, as far as he could recall, the rift "lasted no longer than it took the letter to arrive."

Whatever Trump's personal feelings about Rubenstein's performance, it appears he either got over it or determined there was little value in holding a grudge against someone who traveled in the same elite Manhattan circles that he did. By the mid-2000s, the two were once again enjoying a mutually beneficial relationship. When Rupert Murdoch needed help finding a temporary rental in the city, Rubenstein connected him with The Donald. And while Trump eventually hired the publicist's son, Richard, to represent him, the elder Rubenstein proved in his interview with BuzzFeed News that he still has the talking points down.

“I find him to be one of the most loyal persons I’ve dealt with in my 62 years in my own business,” Rubenstein said, adding that “if you’re loyal in terms of integrity and honesty, he will show you integrity.”

While Trump's own track record of personal loyalty might be mixed, there is no question that he demands it from his employees. To work directly under Trump is to cede virtually all of your time and attention to serving him. Even after falling out bitterly with Trump, some ex-employees recall the highs and lows of the experience with a certain degree of fondness.

As Blanche Sprague, one of Trump's former executives, told the Washington Post in 1987, "To work for Donald you absolutely have to love him, because he will absolutely drive you crazy. There are days when I could cheerfully bludgeon him to death. He starts calling you at 6 in the morning and finishes at 11 at night."

Sprague, whose stylistic similarities to her boss were noted in the press in the '80s, was a key figure in the early days of The Donald's empire-building. Perhaps inevitably, their productive relationship ended in a firing, and then a flurry of litigation, and eventually a high-profile volley of insults, accusations, and hyperbole. At one point, Trump claimed that Sprague's fiery behavior had directly caused 63 employees to leave his company.

(Sprague declined to comment for this story, though in a decidedly Trumpian move, she accused BuzzFeed News of running stories "based on tidbits that they picked up from the street,” and advised a reporter to “take your career out of the street.”)

In interviews and speeches, Trump is fond of name-dropping his many famous "friends" (Tom Brady, for example, or Don King) — a rhetorical tic that makes it difficult to identify his actual friendships. But by virtually all accounts, one of Trump's closest friends early in his career was Roy Cohn. An infamous attorney and ex-aide to Joseph McCarthy, Cohn served as a mentor to Trump through much of the '70s and '80s. He hooked the young tycoon up with his powerful New York political connections, and exploited relationships with the mayor and others to help deliver for Trump the Commodore hotel, a decrepit teardown above Grand Central that he transformed into the Grand Hyatt. Trump held up his end of the friendship as well: When Cohn was facing disbarment in the mid-'80s, Trump testified on his friend's behalf as a character witness. For a while, according to Vanity Fair, the two men spoke "15 or 20 times a day."

Then Trump found out Cohn was HIV-positive.

He moved swiftly to cut ties with his mentor, seeking out new attorneys and transferring his legal business to them. The sudden rejection stunned Cohn. Commenting on the betrayal, Cohn reportedly said, "Donald pisses ice water."

“I don’t know how he found out that Roy was HIV positive, and then it was like, boom, gone,” recalled Susan Bell, Cohn’s longtime secretary, in an interview. “Which was kind of shocking because they were friends. But who knows Donald’s motives? I assume he didn’t want to associate himself with somebody tainted.”

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