From his picture window overlooking New York’s Central Park, Donald Trump could see the public ice rink that the city government had spent six years and $12 million trying — and failing — to repair. Most people saw the shuttered rink as a maddening waste of public dollars. Trump saw an opportunity to lead.
In 1986, Trump, then a brash newcomer in the New York real estate industry, offered to fix the rink in six months at his own expense. Trump’s move was at once bold, magnanimous and biting. In the same letter in which he made his offer to New York Mayor Ed Koch, Trump reminded the mayor that the “incompetence” the city had demonstrated in the rink project had to be “one of the great embarrassments of your administration.”
Trump got the job done two months ahead of schedule and $800,000 under budget. The city paid for the work — the mayor insisted on that — but Trump slapped his name all over the place and generated months of adoring press. For decades to follow, the story of how he swooped in like Superman to save the day became a bedrock foundation of the Trump mythos, his carefully polished narrative of the billionaire who led by smashing through rules and expectations.
The man who now moves from his very own gilded skyscraper on Fifth Avenue to noticeably smaller and less lavish quarters in Northwest Washington is the most unusual leader Americans have ever elected to manage their nation. He is a salesman, not a diplomat; a master marketer, not a bureaucratic manager. He is an entrepreneur who has always thrived on controversy and confrontation, bucking up against the establishment types who often sneered at him.
As president, Trump seems eager to lead in very much the same ways as he has through four decades as frontman for his personal brand.
America, he promised in the campaign, will “win so much, you’ll get tired of winning.” Already, he has launched what he hopes will be a cavalcade of victories. Just three weeks after his November win, the president-elect reached into his box of finely honed tools and pulled out his favorites — surprise and showmanship — to craft a small triumph for workers at a Carrier plant in Indiana: 800 jobs now wouldn’t be moved to Mexico.
Critics contended that the number of workers involved was insignificant in a nation of more than 300 million people, but Trump accomplished just what he’d achieved in the ice rink incident 30 years earlier: He burnished his reputation as a leader who makes deals happen, even if the process isn’t pretty, even if egos and precedents get smashed. And Trump demonstrated that he intends to govern as much by anecdote as by principles or policies.
Trump brings to Washington a leadership style built on his father’s success in the rough-and-tumble world of developing apartment buildings in New York’s outer boroughs, and refined under the tutelage of Roy Cohn, the infamous Manhattan lawyer who taught young Donald that all publicity is good publicity and that victory comes only to those who fight back a hundred times harder than any hit they might absorb.
Trump built a real estate empire that morphed into a casino gambling business, which largely failed, driving the struggling mogul to pivot into a period of leasing his name to all manner of luxury and not-so-fancy products. Through it all, Trump spent much of his time not on the finances of his initiatives or on their daily management, but rather on cultivating his own image as a playboy billionaire who was bluntly decisive, refreshingly impolitic and singularly devoted to all things Trump.
He rewarded loyalty (he called himself “a loyalty freak”), summarily sacked those who showed him up, and won fame and sometimes fortune as he put himself center stage in all his enterprises.
“The show is Trump and it is sold-out performances everywhere,” he said in 1990, soon after he appeared on the cover of Playboy, brushing against a cover girl who eyed him adoringly.
The show — Trump has often called himself a “ratings machine” — is very much at odds with the private nature of the man, a loner who says he has few, if any, close friends, an insomniac who often leaves social events as quickly as possible, returning to his apartment to watch TV by himself through the small hours of the night.
In public, though, Trump is all business and all show, blending the two in ways that have now shattered the boundary between politics and celebrity.
As he launched his career in real estate, Trump broke with his father, who had warned him against taking on debt or working in the tough market of Manhattan. Donald longed to reach for the next level and build in midtown, and he did it by creating a business that looked bigger, bolder and brasher than the competition. He led that business into the big time with tough, loud, showy tactics that he would hone through the decades, methods that became familiar to all Americans through the 2016 campaign and into the presidential transition.
Trump led by creating an image of himself as a rich playboy with fabulous connections in media, politics and entertainment — and by parlaying that image into actual deals with the city’s rich and powerful. He led by making competitors, government regulators and bankers believe he was farther along than he really was. And he led by neutralizing or even winning over his opponents by attacking, threatening, wooing and even hiring them.
During his very first project, the rehab of New York’s decrepit Commodore Hotel in the mid-1970s, Trump persuaded a New York Times reporter to write about him as “a major New York builder,” though he had never built a thing and had no financing. Trump needed top New York politicians’ cooperation to get his hotel project underway, and so he hired Gov. Hugh Carey’s chief fundraiser, who had key political connections. It didn’t hurt that Trump and his father had donated more money to the governor’s campaign than anyone but the candidate’s brother.
Trump wasn’t shy about touting his ties to power. He took the head of New York’s Port Authority, a major landowner in the city, to lunch and asked for his help. “You wouldn’t last in your job very long if Governor Carey decided you weren’t doing the right thing,” Trump told Port Authority director Peter Goldmark, according to Goldmark. “You should know I have a lot of weight in Albany.”
Trump denied Goldmark’s account, saying, “I really don’t talk that way.”
Similarly, in the push for the same project, Trump sought a tax exemption from a state authority created to build racially integrated housing. The agency’s chairman, Richard Ravitch, had grown up in the real estate business; Trump’s father had hired Ravitch’s father’s construction firm to build Trump’s largest apartment complex. Now Donald met with Ravitch and told him, as Ravitch recalled, “I want you to give me a tax exemption.”
Ravitch declined. Trump repeated the request, and when Ravitch declined again, Trump said, “I’m going to have you fired.” Trump, in an interview last summer, denied that account and called Ravitch “a highly overrated person.”
Trump wasn’t done. When city politicians who were opposed to the tax incentive called a news conference outside the shuttered hotel, Trump showed up and threatened to abandon the project if the city didn’t give him tax relief. Trump had prepared for the event by directing his workers to replace the clean boards over the once-grand hotel’s windows with dirty scrap wood, dramatizing the state of the midtown eyesore. The theatrical flourish had the desired impact. Trump got the exemption.
For four decades, Trump led his business empire through triumphs and disasters, through domination of the Atlantic City casino world and through six corporate bankruptcies, devoting his time and energy perhaps above all to his dealings with the news media.
The “key to the way I promote is bravado,” he wrote in his best-selling book, “Trump: The Art of the Deal.” “I play to people’s fantasies. People may not always think big themselves, but they can still get very excited by those who do. That’s why a little hyperbole never hurts. . . . I call it truthful hyperbole. It’s an innocent form of exaggeration — and a very effective form of promotion.”
In business and in the 2016 campaign, he alternately bashed reporters and privately treated them to praise and access. “From a pure business point of view,” he wrote, “the benefits of being written about have far outweighed the drawbacks. . . . Even a critical story, which may be hurtful personally, can be very valuable to your business.”
Reporters who covered Trump through the years told stories of his abusive, epithet-packed phone calls, sometimes in the same day as his generous, complimentary offers of juicy scoops.
His longtime construction executive Barbara Res said that “Donald had a way of getting to print whatever he would say, even if it weren’t necessarily the whole and honest truth. He managed to say what he would say, and people would write it, and then it would be the truth. That was the thing with him that they call the big lie. You say something enough times, it becomes the truth.”
Asked how he shaped his image by working the media, Trump flashed an impish smile, shrugged his shoulders and repeated his mantra that “all publicity is good publicity.”
Trump has refined the art of working the levers of public opinion to pressure those who would block his initiatives. In 1985, after he bought the Mar-a-Lago estate in Palm Beach, Fla., Trump broke with the traditions of the wealthy enclave by chopping down his hedges to give gawkers a clear view of his castle, inviting a raft of celebrities with the accompanying paparazzi, and opening the facility for wedding and event rentals.
The town council, annoyed by the increased traffic and attention, tried to impose restrictions on street use and party attendance. Trump responded by sending council members classic movies about discrimination — “Gentleman’s Agreement,” about anti-Semitism, and “Guess Who’s Coming to Dinner,” about racism — to remind them and the public about how the town had long tolerated the exclusion of Jews and blacks from private clubs in Palm Beach.
The effort to embarrass the politicians into easing restrictions on his club, which was open to all who could afford it, was successful.
He recognized early on that his primary talent lay in marketing his brand, more than in managing day-to-day operations. In 1988, when Jeffrey Breslow, the inventor of many successful board games, visited Trump to pitch him on a Monopoly-like game that would be named after him, the game developer was prepared to get down on the floor and demonstrate how “Trump: The Game” was played.
But Trump had no interest in the details of the game. “I like it — what’s next?” Trump said, and after the deal was negotiated, Trump volunteered to hold a press event at the plant where the product would be manufactured. His best value, he said, was in motivating the workers and winning media attention.
Throughout his career, Trump has measured success by the reach and power of his reputation and image. All of his ventures, in gambling, sports, television and politics, were designed to spotlight the message that “Trump” means ambition, wealth and success.
He always worked with a tiny inner circle of top executives — his campaign staff was about a tenth the size of Hillary Clinton’s — remaining loyal to those who played by his rules: No one steps out on their own, all credit goes to the boss, and the message to the public is that Trump — the man, not the corporation or its other executives — is the rainmaker.
If Trump believes an executive has done something behind his back, he pounces: “You have to realize that people — sadly, sadly — are very vicious,” he told an audience at a motivational seminar in 2005. “When a person screws you, screw them back 15 times harder.”
He hires for loyalty but also to build a staff that looks the part — a factor he has often mentioned through the years, including during this winter’s transition, when he would comment to aides about whether job candidates presented themselves in ways that would convince a TV audience that they were right for the job.
But Trump’s methods for picking people can also be more subtle. Throughout his career, he has hired people who had been obstacles to his projects, both to neutralize their opposition and take advantage of their knowledge. In 1989, when a New York real estate analyst Trump had never heard of went on a TV news show and opined that Trump had taken on too much debt, overpaid for properties and now faced a severe decline in his business empire, Trump filed suit against the man, Abe Wallach, alleging slander and defamation. But Trump then invited Wallach to see him and offered him a job as executive vice president for acquisitions and finance. Wallach accepted and stayed for 12 years. (Trump did not know through most of that period that Wallach had been convicted of at least two felonies before joining Trump’s business, according to a spokesman for Trump.)
In addition to defusing the opposition, Trump hires to create rival power centers. Many Republican leaders thought Trump would have to choose between Republican National Committee chairman Reince Priebus and former Breitbart News chairman Stephen K. Bannon to set the tone for the leadership of his White House. But Trump hired both men — the establishment choice and the rogue outsider — and gave them equal billing in his hiring announcement. Through the years, Trump has similarly hired opposing voices, both to prevent any one faction of his operations from gaining too much power, and to put competing views in play to see which might prevail.
When a group of Silicon Valley tech executives visited with Trump in December, he told them: “You’ll call my people. You’ll call me. It doesn’t make any difference. We have no formal chain of command around here.”
Building such uncertainty and unpredictability into his leadership and decision-making allows Trump to float possibilities, test ideas and remain antagonistic to the powers that be — all before he puts a decision into play. Add his infamous lack of impulse control — his predawn tweets, his thin-skinned reaction to criticism, his insulting comments about people he’s already defeated — and a short attention span — he said he has no patience for reading reports or briefings — and the result is something not quite like any previous occupant of the White House.
But will he even make 1600 Pennsylvania Ave. NW his regular work address? Trump has said he plans to continue his campaign-style rallies around the country through his presidency, and he wants to spend a good chunk of time where he’s most comfortable, inside Trump Tower.
If he follows his life’s pattern, he will leave the day-to-day administration of the government to his top aides, much as Ronald Reagan did. But unlike Reagan, Trump is unlikely to stand aside as he puts his governing philosophy into play. He is demanding and impatient with his staff, and anything but shy about making his displeasure known. But he is not the boss Americans got to know on “The Apprentice”; his top executives say that in real life, he rarely fired anyone and was far from the cavalier brute he portrayed on TV.
He listens well and takes advice, said Res and other top Trump staffers. But there was never any master plan, just as there was no organizational chart. There was just Trump at the center of all things — the definition of Trump being Trump.
He scoffs at deep study and goes, instead, with his gut. He believes in his instincts. He believes he will naturally do the right thing. He believes, as he wrote in his book, “Think Like a Billionaire,” that “a narcissist does not hear the naysayers. At the Trump Organization, I listen to people, but my vision is my vision.”