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 Jersey 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
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. "
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.
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.
"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.'"
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.
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.
"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.