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

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.

Donald Trump through the years
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Donald Trump through the years

Donald Trump with Alfred Eisenpreis, New York City Economic Development Administrator. Sketch of new 1,400 room Renovation project of Commodore Hotel.

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Donald Trump pauses in his apartment 5/20 after receiving the news that the Board of Estimate unanimously approved a 40-year tax abatement plan. Under the plan Trump will purchase and refurbish the Commodore Hotel, which closed into doors 5/18, from the Penn Central Transportation Corp. In return for his $10-million-dollar purchase and up to $100 million face-lifting investment, Trump will have no real estate taxes for 40 years.

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Real estate developer Donald Trump announces intentions to build a $100 million dollar Regency Hotel.

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Donald Trump stands behind architect's model of City Hall Plaza.

(Photo by Frank Russo/NY Daily News Archive via Getty Images)

Donald Trump and Ivana Trump attend Roy Cohn's birthday party in February 1980 in New York City.

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Donna Mills and Donald Trump during 1983 Annual American Image Awards at Sheraton Center in New York City, New York, United States.

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Donald Trump attends 38th Annual Horatio Alger Awards Dinner on May 10, 1985 at the Waldorf Hotel in New York City.

(Photo by Ron Galella/WireImage)

Portrait of real estate mogul Donald John Trump (b.1946), smiling slightly and facing to his right, 1983. New York.

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Boxing promoter Don King holds up the arms of Mike Tyson and former champion Larry Holmes during a press conference here 12/1. Looking on is Donald Trump. The fight will be held at the Trump Plaza Hotel.

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Donald Trump, real estate mogul, entrepreneur, and billionare poses in the foyer of his home in August 1987 in Greenwich, Connecticut.

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Donald Trump Jr. and Donald Trump during 1988 U.S. Open - September 3, 1988 at Flushing Meadows Corona Park in Queens, New York, United States.

(Photo by Ron Galella, Ltd./WireImage)

Ivana Trump and Donald Trump during Mike Tyson vs Michael Spinks Fight at Trump Plaza - June 27, 1988 at Trump Plaza in Atlantic City, New Jersey, United States.

(Photo by Ron Galella/WireImage)

Billionaire Donald Trump and his wife Ivana arrive 04 December 1989 at a social engagement in New York.

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Donald Trump and Daughter Ivanka Trump during Maybelline Presents 1991 Look of the Year at Plaza Hotel in New York City, New York, United States.

(Photo by Ron Galella/WireImage)

Donald Trump attends 'Hoop-La' Special Olympics Basketball Game on June 25, 1992 at the Plaza Hotel in New York City.

(Photo by Ron Galella/WireImage)

Donald Trump and Joan Rivers during Opening of The Rose Room in the Plaza Hotel at Plaza Hotel Rose Room in New York City, New York, United States.

(Photo by Ron Galella, Ltd./WireImage)

Donald Trump touches 07 April 1993 Marla Maples stomach to confirm published reports that the actress is pregnant with his child. The two arrived for Maples appearance in the Broadway musical 'The Will Rogers Follies'.

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US business tycoon Donald Trump enters the PLaza Hotel in New York past supporters 21 December 1994. Hundreds of supporters showed up at a news conference where Trump denied a New York newspaper report that the Sultan of Brunei had bid 300 million USD to buy the Manhattan hotel.

(Photo credit should read DON EMMERT/AFP/Getty Images)

Donald Trump and Christine Whitman during Opening of New Warner Bros. Store in Trump Plaza Casino at Trump Plaza Casino in Atlantic City, New Jersey, United States.

(Photo by Ron Galella/WireImage)

Donald Trump attends Marc Jacobs Fashion Show on April 4, 1995 at the Plaza Hotel in New York City.

(Photo by Ron Galella/WireImage)

Boxing: IBC Heavyweight Title: View of celebrity businessman Donald Trump and actor Steven Seagal seated ringside during Lennox Lewis vs Tommy Morrison fight at Boardwalk Convention Hall. Atlantic City, NJ. (Photo by John Iacono /Sports Illustrated/Getty Images) 

New York real estate giant Donald Trump poses in his Trump Tower office on a giant letter 'T' on May 8, 1996.


Portrait of Marla Maples and her husband, businessman Donald Trump, with their daughter Tiffany, as they pose together at the Mar-a-Lago estate, Palm Beach, Florida, 1996.

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Donald Trump and Ron Delsner backstage at a KISS concert at Madison Squre Garden in New York City on July 25, 1996.

(Photo by Ebet Roberts/Redferns)

Donald Trump attending Halloween party thrown by Naomi Campbell and Kate Moss at the Supper Club to kick off Fashion Week.  

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Donald Trump open his new building at 1 Center Park West- The new Trump International Hotel and Tower.

(Photo byJames Hughes/NY Daily News via Getty Images)

Donald Trump and his girlfriend Celina Midelfar watch Conchita Martinez and Amanda Coetzer 07 September at US Open in Flushing Meadows, NY.


Celine Dion, husband Rene, Donald Trump & Ivanka Trump

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Entrepreneur Donald Trump and Rev. Al Sharpton speak at a ribbon cutting ceremony for Sharpton's National Action Network Convention April 5, 2002 in New York City. The group aims to further the development of civil rights.

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Donald Trump and his girlfriend Melania Knauss attend the Marc Bouwer/Peta Fall/Winter 2002 Collection show February 14, 2002 during Mercedes-Benz Fashion Week in New York City.

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Donald Trump at Madison Square Garden

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Donald Trump stands on the sidelines before the start of the AFC divisional playoffs between the New England Patriots and Tennessee Titans on January 10, 2004 at Gillette Stadium in Foxboro, Massachusetts. Temperatures have reached as low as 7 degrees in the Foxboro area.

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Donald Trump, Visionary Business Leader award honoree, poses with his children Donald Trump Jr. and Ivanka at Fashion Group International's 22nd Annual 'Night Of Stars' at Cipriani's 42nd Street October 27, 2005 in New York City.

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Eric Trump and Donald Trump attend the Chicago Bulls vs New Jersey Nets game at the IZOD Center on October 31, 2007 in East Rutherford, New York.

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 Donald Trump delivers a speech with his son Barron after he was honored with the 2,327th star on the Hollywood Walk of Fame on Hollywood Boulevard in Hollywood, CA, 16 January 2007.


Portrait of former model Melania Trump and her husband, businessman Donald Trump, as they sit together at a table during the 16th annual 'Lady in Red' gala, hosted by LIFE (Leaders In Furthering Education), at the Mar-a-Lago club, Palm Beach, Florida, December 4, 2009.

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Donald Trump sands with Miss Universe 2009 Stefania Fernandez of Venezuela prior to the Miss Universe 2010 Pageant Final at the Mandalay Bay Hotel in Las Vegas on August 23, 2010. Miss Universe is an annual international beauty pageant and along with the Miss World is the most publicized beauty contest in the world. California clothing company Pacific Mills founded the contest 1952 and was acquired by Donald Trump in 1996.


US tycoon Donald Trump arrives to speak at the annual Conservative Political Action Conference (CPAC) at National Harbor, Maryland, outside Washington, on February 27, 2015.


Donald Trump speaks during the NRA-ILA Leadership Forum at the 2015 NRA Annual Meeting & Exhibits on April 10, 2015 in Nashville, Tennessee. The annual NRA meeting and exhibit runs through Sunday.

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Real estate mogul and billionaire Donald Trump attends Golf legend Jack Nicklaus' Congressional Gold Medal ceremony in the U.S. Capitol Rotunda March 24, 2015 in Washington, DC. Trump announed on March 18 that he has launched a presidential exploratory committee.

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Businessman Donald Trump speaks to guests gathered for the Republican Party of Iowa's Lincoln Dinner at the Iowa Events Center on May 16, 2015 in Des Moines, Iowa. The event sponsored by the Republican Party of Iowa gave several Republican presidential hopefuls an opportunity to strengthen their support among Iowa Republicans ahead of the 2016 Iowa caucus.

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Republican Presidential Candidate Donald Trump visits his Scottish golf course Turnberry with his children Ivanka Trump and Eric Trump on July 30, 2015 in Ayr, Scotland. Donald Trump answered questions from the media at a press conference.

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U.S. President-elect Donald Trump speaks at his election night rally in Manhattan, New York, U.S., November 9, 2016.

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Singer Kanye West and President-elect Donald Trump speak with the press after their meetings at Trump Tower December 13, 2016 in New York.


Republican U.S. presidential candidate Donald Trump poses for a photo after an interview with Reuters in his office in Trump Tower, in the Manhattan borough of New York City, U.S., May 17, 2016.

(REUTERS/Lucas Jackson)

 Coverage of the 2016 Republican National Convention from the Quicken Loans Arena in Cleveland, Ohio, which airs on all ABC News programs and platforms. On this final night of the convention, Donald Trump accepts the party's nomination for President of the United States.

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U.S. Republican presidential candidate Donald Trump reacts to an answer his wife Melania gives during an interview on NBC's "Today" show in New York, April 21, 2016.

(REUTERS/Brendan McDermid/File Photo)

President-elect Donald Trump speaks to reporters following his meeting with Jack Ma, Chairman of Alibaba Group, meeting at Trump Tower, January 9, 2017 in New York City. President-elect Donald Trump and his transition team are in the process of filling cabinet and other high level positions for the new administration.

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U.S. President Donald Trump and Israeli Prime Minister Benjamin Netanyahu shake hands after Trump's address at the Israel Museum in Jerusalem May 23, 2017. REUTERS/Ronen Zvulun TPX IMAGES OF THE DAY
U.S. President Donald Trump has coffee during a reception ceremony in Riyadh, Saudi Arabia, May 20, 2017.Bandar Algaloud/Courtesy of Saudi Royal Court/Handout via REUTERS ATTENTION EDITORS - THIS PICTURE WAS PROVIDED BY A THIRD PARTY. FOR EDITORIAL USE ONLY. TPX IMAGES OF THE DAY
U.S. Vice President Mike Pence (L) and U.S. President Donald Trump appear on stage at a rally in Harrisburg, Pennsylvania, U.S. April 29, 2017. REUTERS/Carlo Allegri TPX IMAGES OF THE DAY
U.S. President Donald Trump holds up a U.S. Air Force Academy football jersey that was presented to him by team captain Weston Steelhammer during the presentation of the Commander-in-Chief trophy in the Rose Garden of the White House in Washington, U.S., May 2, 2017. REUTERS/Joshua Roberts TPX IMAGES OF THE DAY
U.S. President Donald Trump delivers the keynote address at the U.S. Holocaust Memorial Museum's "Days of Remembrance" ceremony in the Capitol Rotunda in Washington, U.S, April 25, 2017. REUTERS/Kevin Lamarque TPX IMAGES OF THE DAY
U.S. President Donald Trump, U.S. first lady Melania Trump, their son Barron and the Easter Bunny arrive for the 139th annual White House Easter Egg Roll on the South Lawn of the White House in Washington, U.S., April 17, 2017. REUTERS/Joshua Roberts TPX IMAGES OF THE DAY

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'

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.'"

APAs 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 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.'"

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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