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If you want to understand Trump, look at his early relationship with the man he has called his best friend

George Steinbrenner and Donald Trump
George Steinbrenner and Donald Trump

(George Steinbrenner and Donald TrumpAP Photo/Ed Bailey)

On February 8, 1984, a few of the most prominent businessmen in New York — members of the New York State Urban Development Corporation — were holding a news conference.

Among them was a press darling — a man whose brash reputation and penchant for public tirades had made him one of the city's most recognizable figures.

His rise to prominence a decade earlier sprung from his purchase of a major New York institution. He was tall, an imposing figure with his hair just long enough to be swept flat behind his ears. He often bellowed, "You're fired!," a connotation embraced by households across the country.

Standing nearby at that news conference was Donald Trump.

The man he was watching was George Steinbrenner, the owner of the New York Yankees. Known simply as "The Boss," Steinbrenner is the man Trump has called his best friend.

Trump doesn't toss around such a label frequently, at least in the press. But in Steinbrenner, the famed, bombastic owner, Trump saw a role model.

Steinbrenner's flair was something Trump came to emulate — and, in many, ways surpass. It was evident in his business career, on television, his political rise, and eventually, in the beginnings of his once-unthinkable presidency.

Ray Negron, a Yankees employee for more than 40 years who serves as a columnist for Newsmax, told Business Insider that Steinbrenner was a "very strong mentor" to Trump.

"Especially going back into the 70s, when George won the championships and Trump was buying the football team," Negron said, referring to Trump's purchase of the USFL's New York Generals. "He spent a lot of time in talking to George about the appropriate ways and et cetera and he took everything to heart."

"And he looked at Steinbrenner as a big brother, as a hero, and you know he don't look at anybody that way," Negron continued. "They were both the same."

As the Yankees prepare to open their 2017 season Sunday and Trump navigates through the early throes of his presidency, signs of Steinbrenner's influence on Trump — and his family — linger. On Thursday, Donald Trump Jr. posted a photo on Instagram of himself with his father and Steinbrenner.

"I certainly didn't get the magnitude of this NY moment at the time but I definitely do now. Really amazing history there," he wrote.

The White House did not respond to requests for comment for this story.

'They had a lot of things in common'


(Trump and Steinbrenner.AP Photo/Mario Suriani)

For Negron, the comparisons began with both men's fathers.

Trump's father, Fred, wasn't too keen on the young developer's decision to enter the Manhattan market, instead insisting that the younger Trump should continue with the family's outerborough real estate business, in which it had found its initial success.

Steinbrenner's father, Henry, wasn't terribly enthused with his son's decision to buy the Cleveland Pipers, a professional basketball team. The younger Steinbrenner's venture was nothing short of an abject failure, but his next venture in sports ownership proved infinitely more successful.

Like Trump, Steinbrenner had gotten his start in the family's successful business. In his case, it was the family's shipping company.

"All these different variables, they had a lot of things in common," Negron said. "Throughout the years he always called Mr. Steinbrenner ... in any type of scenario. He would always checked in on him, and 'The Boss' always gave him what he thought was the right advice."

Negron said it was quite common to hear Steinbrenner's secretary alerting the owner "Mr. Steinbrenner, Trump on [line] two."

He made note that Trump borrowed his trademark phrase for his NBC show, "The Apprentice," from Steinbrenner, who first popularized "you're fired" in his years-long, love-hate relationship with manager Billy Martin, whom Steinbrenner hired and fired a total of five times.

Trump "borrowed that from the great George Steinbrenner, and people forget that," Negron said. "I even used to ask 'The Boss' if he got upset with that and he said, 'Imitation is the greatest form of flattery.'"

A controversial figure in his own right, Steinbrenner found himself in trouble at various points of his career. There were the illegal campaign contributions to President Richard Nixon. Years later, he paid to have dirt dug up on a star Yankees player, Dave Winfield. At both points, he served suspensions from Major League Baseball. In the first, he pleaded guilty to criminal charges for which he was later pardoned by President Ronald Reagan.

And Steinbrenner, as evidenced by his tumultuous relationship with Martin, was known to be an extremely tough person to work for.

"I can only say, I remember one time, one of [Trump's] employees who's a dear friend said to me when I called him up — and I could see he was in a real, really bad mood," Negron said. "And I said, I asked him 'What's wrong, bro, what's wrong?' And he says to me, 'Listen, you work for somebody like him, you know what's wrong.'"

young donald trump
young donald trump


As New York Times columnist Maureen Dowd wrote just days before the November election, Steinbrenner was one of the "towering characters" Trump began to hang around as his profile began to grow. She wrote that "from Steinbrenner, he learned about indiscriminately grabbing the limelight":

"As Trump once said to his Yankee pals, 'good publicity, bad publicity, as long as it’s publicity.' They would sit in Steinbrenner’s suite at a big conference table watching Reggie Jackson slug home runs on TV. They got together all over town, especially at Elaine’s and Le Club, a hub in Midtown for wealthy guys, models and actresses.

"'Donald was not a big night life person, except for Le Club,' said one former Steinbrenner staffer. 'He was always very likable in those days. He had a big personality, but he was the youngest of the group. He was never arrogant or full of himself. He always was respectful and pleasant to everybody.'

"Steinbrenner taught his protégé too well. When Trump asked his pal for the contract to build the new Yankee Stadium, the Boss said no. 'If I do that,' he said, 'it’s gonna be Trump Stadium, not Yankee Stadium.'"

Michael O'Keeffe, a former New York Daily News columnist who now works at Newsday, seconded Dowd's sentiment. He told Business Insider that from Steinbrenner and the "Le Club" crowd, Trump learned how to be "larger than life." Both Steinbrenner and Trump also sometimes said inflammatory things off the top of their heads without fully considering the ramifications, he added.

But to O'Keeffe, there was a "big difference" between the two bombastic men.

"George was very competent at what he does," O'Keeffe said. "And I think what we're seeing from this White House is they're kind of all over the place. Trump makes statements, whether it's about the size of his inaugural crowd or Obama wiretapped him or what have you, that just don't get backed up. There's just no evidence to back them up."

"And I think that, you know with George, he really cared about competence," he added. "He cared about putting the right people in the right jobs. ... I think he would, from my own observation of him, he would probably feel less confident about Trump, especially given some of the cabinet picks."

O'Keeffe wrote just prior to the November election that, if Steinbrenner, who died in 2010, were still alive, he would've voted for Democratic presidential nominee Hillary Clinton. The columnist said Steinbrenner had expressed admiration for Clinton to him in the past.

His readers did not seem to agree with that assessment.

"I got a lot of feedback from that column," he said. "I got a ton of emails, some really ugly: People just saying 'you're a f------ idiot, you're a f------ moron. George would be for Trump!'"

O'Keeffe said a Yankees employee even doubted him, telling the Daily News columnist "'you're just wrong about that. He liked Trump, he hung around with Trump.'"

"It was like 95% negative," O'Keeffe said of the reaction to his column. "And I think the 5% was my mother and my editor."

Whether or not he would've voted for his old pal, Negron is confident that, even though Trump is president, the mentor-protégé relationship between the two would still be evident.

"I've seen the biggest stars in the world stop and kiss 'The Boss's' ring," Negron said. "And you're talking about the [Frank] Sinatra's, you're talking about the Cary Grant's, the biggest of the big, and if the boss was alive today, and Trump was the president, I guarantee you he would kiss his ring too."

He 'understood winning better than anybody'

After Steinbrenner's death, Trump wrote how his "great friend" was a "true legend" who "understood winning better than anybody."

"There will never be anyone like him in New York," Trump wrote on Facebook. "The country has lost a truly great man."

The level of admiration seeped through in a more extensive Trump statement at the time of the famed baseball owner's death:

"George Steinbrenner was not only an icon, he was a friend and a very great man. He also knew what winning is and what winning meant. It meant everything — and everything is what it took to achieve it. If you know anything about George, you'll know he was focused and incredibly tenacious. He knew what he wanted, what his vision for the Yankees was, and he went at it 100% on every level.

"Every detail mattered to him and the bottom line is that his tenacity worked. He refused to give in under any circumstances and he made the Yankees a great team. There will never be another George and he gave us some of the greatest moments in the history of baseball. He also gave us an example to remember: go for it, no matter what, and give it all you've got and more. His generosity of spirit was without equal. He'll be greatly missed."

In the years that followed, Trump posted a number of tweets in which he mentioned Steinbrenner, many of which also dealt with a longstanding annoyance he had with then-Yankees third baseman Alex Rodriguez.


(Trump, Donald Trump Jr., George Steinbrenner, and Billy Martin.AP Images/Richard Drew )

Trump wrote that Steinbrenner "would have done a major number" on the Yankees star and "would have gotten out of" his contract long ago. He also wrote that the team was "sure lucky" Steinbrenner was no longer around — the team is currently run by his two sons, Hal and Hank — because "a lot of people would be losing their jobs." After a postseason departure, Trump wrote again that the team was "lucky" they didn't "have to deal with George Steinbrenner."

"The Yankees really have to be embarrassed losing all four games to the Mets — my great friend George Steinbrenner would be going nuts!" he wrote after the Yankees' crosstown rivals swept them in 2013.

While Trump heaped praise through the decades on Steinbrenner for being a "winner," perhaps the most important skill he learned was the ability to "work the political system," something he boasted of for months along the campaign trail.

"I think his relationship with Steinbrenner showed him how wealthy guys work the political system," longtime Trump political adviser and confidant Roger Stone told Business Insider. "Steinbrenner was a guy who gave millions and millions of dollars to politicians and political parties. And he worked 'the system.'"

Trump and Steinbrenner
Trump and Steinbrenner

(Trump and Steinbrenner.AP Photo/Teddy Blackburn)

Stone said Steinbrenner was "a patriot" and "a man's man in a John Wayne type sense."

"He's a very commanding guy, and he was friendly with every politician," he continued. "Every president, every mayor, every governor or New York knew George Steinbrenner. He's one of the most famous New Yorkers there were, and he was a cheerleader for the Yankees. And who doesn't love the Yankees in New York?"

Included among those who loved Steinbrenner's Yankees was Nixon himself. And Nixon, whom Trump emulated to an extent along the campaign trail, met the future president while attending a Yankees game in Steinbrenner's box.

It was back in 1987. As Stone retells the story, Nixon expressed to him afterward that he felt Trump had the ability to make a successful run at the White House, or as Stone said the ex-president said, "'he could go all the way.'"

He was one of the first to do so.

As Stone put it: "He saw it before anybody, with the possible exception of Donald Trump."

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