A balanced history of Donald Trump and the New York Yankees

Because of my strong focus on the China Virus, including scheduled meetings on Vaccines, our economy and much else, I won’t be able to be in New York to throw out the opening pitch for the @Yankees on August 15th. We will make it later in the season!

— Donald J. Trump (@realDonaldTrump) July 26, 2020

Whether Trump gets to throw out a first pitch this season or not, there is an important story to be told about his capricious dalliances with baseball. More pertinently, there is a complex and somewhat uncomfortable relationship between the president and his hometown Yankees that spans five decades. I want to explore that murky phenomenon and present a full, unbiased history of Donald Trump and the baseball team with which he is most immediately associated.

Accordingly, this is the story of a US president and his complicated love affair with the New York Yankees. Some will be offended by these tales. Others will be uncomfortable. I simply want to share the details. You can make your own deductions, but this is a story that must be preserved for the historical record. 

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Which team does the president root for? Inside the baseball-crazed childhood of Donald Trump

Donald John Trump was born in Queens, New York on 14^th June 1946. The Yankees were out of town that day, busy beating the St Louis Browns 6-1 before 13,380 at Sportsman’s Park. Joe DiMaggio notched a couple of hits. Phil Rizzuto knocked in a pair of runs. Spud Chandler pitched a complete game five-hitter, and all was right in the pinstriped galaxy.

By all accounts, Trump was something of a bandwagon baseball fan as a kid. He loved individual players more than specific teams, with Yankees catcher Yogi Berra and Brooklyn Dodgers backstop Roy Campanella ranking among his favourites. Indeed, Trump came of age in a halcyon era for New York baseball, with the Giants rounding out a sacrosanct triumvirate of elite city teams. 

An avid collector of baseball cards, Trump often snuck a transistor radio into class to listen to key pennant race games. He liked the Dodgers but also had a soft spot for the Yankees. It was difficult for Donald to root for just one team, an ironic precursor to his political inconsistency.

In 1956, a young Trump lined up with fellow classmates from Kew-Forest school to wave at president Dwight Eisenhower as he passed by in a limousine bound for a Dodgers-Yankees World Series game. Eisenhower threw out the first pitch upon arrival, so perhaps that is when the seed of desire was planted in Trump’s adolescent mind.

When the Dodgers and Giants subsequently moved to Los Angeles and San Francisco, respectively, Trump developed a curiosity for the New York Mets, a National League expansion franchise born in 1962. A handy first baseman, Trump also played baseball at high school, and the Philadelphia Phillies once sent a scout to watch him, according to some industry whispers.

The president claims to have been the best ballplayer in New York state, an extravagant assertion that was summarily debunked by a Slate article that is certainly worth your time. Still, baseball was part of Trump’s formative milieu, and it remained an important cog in his entrepreneurial awakening.

The rise of Trump as a businessman in New York, and how he became friends with George Steinbrenner

The son of Fred Trump, an austere businessman who turned basic real estate into tangible profit, Donald cut his commercial teeth in the outer boroughs of New York. In 1971, he took over the family real estate business, renamed it The Trump Organization, and altered its purview from providing functional accommodation to majoring in lavish retail and professional developments. Where Fred focused on apartments, Donald yearned for hotels, casinos and glitzy skyscrapers. The younger Trump became obsessed with Manhattan, against his father’s advice, and he threw enough darts at the board to eventually succeed.

Accordingly, life was pretty sweet for Donald in the early-1980s. Transplanted onto the Forbes rich list, Trump launched himself into headline-grabbing projects – the more audacious, the better. He mixed in elite circles, carrying an air of majesty and a pout of knowing arrogance. Everything Donald touched turned to gold – quite literally. His buildings pushed the boundaries of faux luxury, replete with pretentious decoration and gaudy trimmings. There was an invincibility to his ascent, and many considered him an unstoppable force.

People were just drawn to Trump in this era. He had a rare magnetism that transcended real estate. At the confluence of tabloid proliferation and the birth of reality television, Donald became a fascinating subject, courting attention with his outlandish personality in addition to the marquee property portfolio. In time, that personality became Trump’s portfolio, and the projects he led morphed into mere accoutrements of the high roller lifestyle. 

In 1984, for instance, Trump bought the New Jersey Generals, a star-crossed franchise in the doomed United States Football League. According to most retellings, Donald reached out to bombastic Yankees owner George Steinbrenner for advice on running a team in such a relentless market. The Yankees had won two World Series titles under The Boss by that point, and Trump was keen to learn from a true powerbroker. George was only too pleased to share his wisdom, and a relationship was fashioned by lawyer Roy Cohn, who had the unenviable task of advising Trump and Steinbrenner during one of the most litigious eras in American history.

Ultimately, Trump picked a great role model in the genre of sports team owners who had little idea what they were actually doing. Sure, Steinbrenner’s teams were occasionally successful, but there was a direct correlation between George easing off the gas and the Yankees winning games. The Bronx Bombers often won in spite of Steinbrenner, not because of him, and some baseball insiders considered him illiterate in the game’s minutiae. There was obvious synergy with Trump’s football frolics, here. Meanwhile, some of Donald’s more harebrained ventures teetered on the brink of bankruptcy for decades, drawing further parallels to Steinbrenner, whose road to championship rings was paved by intermediaries he rarely cared to praise.

Donald and George grew close through their shared pursuit of money, fame and adulation. In March 1986, Trump attended a Yankees spring training game in Tampa, a distinguished guest of Steinbrenner, who left no stone unturned in providing preferential treatment. George and Donald watched the ballgame together, rubbing shoulders with some highflying Chrysler executives, before anarchy broke out in the parking lot. Trump’s car, a Lincoln Continental, was blocked in the VIP garage. On the spot, Steinbrenner fired the intern who parked the vehicle. Trump was apparently impressed, and his baseball allegiances were duly swayed toward the Bronx Bombers.

Associating with the prestigious Yankees was a boon for Trump’s curated image of debonair sophistication. The Yankees were synonymous with success. They almost defined winning. Their brand was recognised around the globe, and Trump held similar ambitions for himself. By comparison, the Mets lacked gravitas. Ditching them for the vaunted pinstripes and sacred interlocking NY was a bold publicity stunt, and Donald soon became the master of those. 

What George Steinbrenner taught Donald Trump about business and celebrity

Even though Steinbrenner was 16 years older than Trump, George had an almost reverential respect for Trump. Steinbrenner admired the zeal with which Trump attacked the Big Apple, determined to shape it in his own image. The Donald was American capitalism incarnate, and The Boss often shook his head in amazement. Meanwhile, Trump looked up to Steinbrenner as a dominant businessman with a proven track record of success. Donald stole many mannerisms from George’s paranoid playbook, imitating his role model so successfully that today those trademarks are conflated as Trumpian by genesis.

Trump’s ‘you’re fired’ charade on The Apprentice? Steinbrenner popularised that concept, changing managers 20 times in his first 23 seasons as Yankees owner. George bordered megalomania in his micromanagement of staff. Billy Martin, a passionate Yankee, was fired and rehired on five different occasions. “The first time George fires you, it is very traumatic,” Yankees public relations czar Harvey Greene once said. “The three or four times after that, it’s like, great: I’ve got the rest of the day off!”

Steinbrenner also mastered the art of media manipulation, later a key tool in Trump’s arsenal. George had certain beat writers on speed dial, using the tabloids to criticise his managers and faltering superstars alike. The Boss was always good for a juicy quote, and reporters struggling with empty notebooks often poked the hornet’s nest, feeding George incendiary questions. Steinbrenner was rarely out of the headlines, and he moderated his own image in a manner befitting future generations. New York rarely handed out such social ubiquity, but The Boss was different. He was indomitable.

Before long, Steinbrenner was transmogrified into something akin to a mythical caricature. He came to embrace his own reputation as a ruthless boss, appearing as an exaggerated version of himself on popular television shows such as Seinfeld and Saturday Night Live. George leaned into his own monolithic potential as much more than an entrepreneur, and opportunities for further enrichment found him organically.

In many ways, then, Steinbrenner was the prototype of what Trump wanted to become – the big, brash owner who fired people indiscriminately and whose personality was so outlandish as to provide endless fodder for commercials, comedy sketches and talk shows around the world. In time, Trump called Steinbrenner his ‘best friend,’ a label never bestowed lightly, and the two defining families of New York grew closer.

Did George Steinbrenner influence the political views of Donald Trump?

Indeed, if anybody comes close to Trump in attracting labels, categories and stereotypes, it is Steinbrenner, whose legacy is still hotly debated a decade after his death. Some call Steinbrenner the greatest owner in the history of sports, a serial winner who spared no expense in pursuit of glory. Others lament the way George skewed competitive balance in baseball, branding his Yankees corporate and stiff.

Some revere The Boss as the final bastion of untrammelled competitiveness in sports, while others revile the way he was born into easy wealth. Still others focus on Steinbrenner’s bipolar actions, citing mean tropes and heart-touching gestures in equal measure. Every way you dice it, George was a complicated beast. Stop me if this sounds at all familiar.

Like Trump, Steinbrenner was often accused of having questionable political tastes, often tied to the whims of his business empire. In 1974, for instance, George was banned by Major League Baseball after pleading guilty to funnelling illegal donations to the re-election campaign of Richard Nixon, a Republican president. He was later pardoned by Ronald Reagan, another GOP grandee, only to suffer a further baseball suspension in 1990 for paying a seedy gambler to spy on Dave Winfield, one of his own players.

Looking at the headlines, then, it is easy to condemn George Steinbrenner as a staunch conservative, willing to do anything to protect his own wealth. However, on the contrary, The Boss also supported Democrat, liberal and independent politicians over an extended period, including the Clintons, casting his true ideology into doubt. Again, stop me if you have heard this before.

The Florida Republican Party was a big recipient of support from Steinbrenner, who adopted Tampa as his family home. Nevertheless, George hobnobbed with New York politicians of all stripes, striking a rapport with pretty much anyone who could help the Yankees in their quest for a new stadium. Rudy Giuliani, a Republican mayor, was particularly close to Steinbrenner, but George also supported the Kennedys, confusing his confidants.

According to the Centre for Responsible Politics, Steinbrenner gave 44% of his political donations to Republican candidates, 44% to Democrats and 12% to independents. That speaks to a philosophical chameleon who knew the power of campaign dollars in greasing the wheels of progress. George played the game, and few could match his skill or resource.

But what drove The Boss? What lay within his spirit? How was Steinbrenner wired, and did his values influence Trump? Well, the facts are a little unclear. Yet what we can deduce is that, although fundamentally different in many ways, George and Donald shared a similar worldview. They looked at life from a similar perspective.

For example, Steinbrenner was a self-confessed ‘chauvinist’ who never entertained the prospect of his daughters one day owning the Yankees. George even selected Steve Swindal, a mere son-in-law, as his onetime heir apparent. He was obsessed with optics and image, even forbidding beards and white cleats on the New York ballclub. If Steinbrenner said ‘jump,’ the Yankees said, ‘how high?’

In much the same way, Trump has always pushed the boundaries of sleaze and scandal, success and sensibility. The president has faced accusations of misogyny, racism and outright sexual harassment, among other blends of misdemeanour. He operates in the familiar steamroller fashion of Steinbrenner, albeit with less concern for political correctness. Some would brand that ironic when comparing a politician with a baseball owner, but such is the contradictory egotism that makes these families tick.

The similarities between Donald Trump and George Steinbrenner

To that end, the similarities between the Trumps and Steinbrenners span multiple generations. After all, Donald and George both inherited considerable wealth from their fathers, who in turn were hard taskmasters. Henry George Steinbrenner II graduated from MIT first in his engineering class and later built the family shipping empire that George expanded. Meanwhile, as already documented, Fred Trump was a successful businessman in his own right, teaching his son the virtues of thrift.

Donald and George were both enrolled in exclusive military schools, furthering their education. Trump attended New York Military Academy, a private boarding school with decadent uniforms. Similarly, George graduated from Culver Military Academy, a prep college in Indiana. To a certain extent, both men were fashioned in the image of their adolescent surroundings, affecting the stern discipline of such institutions in all walks of future life.

Steinbrenner joined the United States Air Force for a spell after graduation, but neither he nor Trump became known for their military contributions. In fact, Trump managed to avoid several drafts, to his historic detriment, before transitioning to business. Here, Donald and George are similar in that their love of military arcana, rhetoric and symbolism was and is grounded in little tangible experience.

With regard to offspring, George had his first child, Hank, in April 1957, aged 27. Donald had his first child, Donald Jr., in December 1977, aged 31. Steinbrenner ultimately raised four children in total – two boys and two girls - while Donald is a five-time parent with three sons and two daughters. One imagines those individuals have a whole lot in common.

The similarities between Donald Trump Jr., and Hal Steinbrenner are particularly interesting, providing a microcosm of life inside large, controversial and patriarchal dynasties. They were born eight years apart – Hal in 1969 and Donald Jr. in 1977 – but they have trodden very similar paths, moulding and bending to the demands of burdensome family lineage.

Hal often ran around the Yankee Stadium clubhouse before working his way through the organisation, while Donald Jr. rose to prominence as a boardroom judge beside his father’s knee on The Apprentice. Both children followed their dads into boarding schools, with Hal continuing the Culver tradition. Nowadays, Hal is managing partner of the Yankees, a team worth $5 billion, while Donald Jr. is the executive vice president of the Trump Organization, which has annual revenues of $700 million.

At times, it has been borderline awkward to watch Hal and Donald Jr. emerge clumsily from their respective parental shadows. Both men have the unenviable task of following extraordinary acts from their own household, and each has taken a unique approach to the encore. Whereas Donald Jr. is cast in a similar mould to his father, sharing his bluster and defending his views, Hal is the antithesis of George, presiding over the new-age Yankees with less volume and more efficiency. It is enthralling to study the difference.

Has Donald Trump thrown a first pitch? Looking back at his MLB (and MiLB) history

Returning to the central theme of this essay – Trump’s fictitious date with the Yankee Stadium mound – it is important to note that, like Steinbrenner, Donald has a natural nose for publicity, and that has often extended to baseball. Amid the screeching hoopla, it is easy to forget that Trump has thrown out ceremonial first pitches at many baseball games in the past. He is just yet to do it as president.

In 2000, Donald threw out the first pitch at Wrigley Field before a Chicago Cubs game. He was then joined by Melania, his wife, to sing Take Me Out to the Ballgame from the broadcast booth.

Additionally, in March 2004, Trump threw out the first pitch before a Yankees-Astros spring training game in Tampa. “George was not happy about it,” Trump said in a 2019 interview. “It cooled my relationship with him for about two days.”

Later that year, in another bizarre episode, Trump landed his private helicopter in centre field at Commerce Bank Ballpark, home to the Somerset Patriots, a minor league team in New Jersey. Wearing a Patriots jacket, Donald threw out the first pitch before posing for photos. The internet is still unsure quite why this star-spangled mindfuck actually took place, but it makes for great fireside discussion.

A few months after the Somerset stunt, Trump became cosy with another Patriots team – the Patriots team, in fact, out in New England. Donald appeared on the sidelines at Gillette Stadium before a 2004 NFL game, befriending star quarterback Tom Brady. Team owner Robert Kraft also became a Trump ally, as did legendary head coach Bill Belichick. Trump even threw out a first pitch at Fenway Park in 2006, to the retrospective astonishment of some. The Yankees played the Red Sox that day, adding another footnote to Donald’s osmosis-like tryst with the team.

More recently, in 2017, a few months after moving into the White House, Trump was invited by the Nationals to throw out the first pitch on Opening Day. Citing schedule conflicts, Trump declined, but many insiders said he hoped to continue the tradition later in his presidency.

By 2019, however, Trump’s reputation had taken such a profound battering that the president was booed when merely introduced from the stands at a Nationals World Series game. The prospect of throwing a pitch barely seemed to be broached due to legitimate security concerns.

The Yankees’ history with politics, religion and presidents

Of course, the Yankees have a rich history of their own with regard to politics, religion and presidents. In an age where commentators are told to ‘stick to sports,’ we often shy away from the intersection of baseball and politics. However, in truth, the two have been interwoven for centuries. They are America’s two greatest pastimes: shouting at people who hit balls over walls, and shouting at people in general.

In 1908, the Yankees – then known as the Highlanders – visited Theodore Roosevelt at the White House while in Washington to play the Senators. Clark Griffith, manager of the Highlanders, publicly endorsed Roosevelt and encouraged him to seek re-election. Not much of a sports fan, Teddy declined, leaving office in 1909.

In later eras, Babe Ruth, Joe DiMaggio and Roger Maris all visited the White House for a range of engagements. Ruth famously earned more than president Hoover in 1930, to the fury of some critics. “What the hell has Hoover got to do with it?,” Ruth famously asked when questioned about his $80,000 salary. “Anyway, I had a better year than he did.”

A Republican, Hoover actually developed a strong affinity with the Yankees, throwing out ceremonial first pitchers at two Old-Timers’ Days, the team’s signature celebration of its alumni. Nevertheless, Franklin D Roosevelt became the first sitting president to throw the first pitch at a Yankees game, doing so during the 1936 World Series. He was followed in that pantheon by George W Bush, whose contributions in 2001 echo through team folklore.

Political ideology aside, I still get goosebumps watching videos of Bush atop the Yankee Stadium mound before Game 3 of that Fall Classic against the Arizona Diamondbacks, exposed to a crowd of 55,820 just seven weeks after the 9/11 terrorist attacks in that same city. There is something magical about it; something so evocatively and unbeatably American. The unity of those moments is spellbinding, and they should never be airbrushed from history.

Likewise, even as an atheist, I’m respectful of the Yankees’ history of engagement with the Roman Catholic church because it adds lustre and significance to the team’s tradition. Pope Paul VI delivered mass to 90,000 at Yankee Stadium in 1965; Pope Paul VI did the same in 1979; and Pope John Paul II continued the tradition in 2008. My beliefs diverge from Catholicism in many ways, but I’m still able to respect and appreciate the magic of those events from an objective standpoint.

Naturally, the Yankees’ dabbling with politics and religion has occasionally caused controversy, and Trump’s recent triangulation is not unique in this regard. Marilyn Monroe, the one-time wife of DiMaggio, is rumoured to have pursued affairs with John F Kennedy and Robert Kennedy, political titans. To that end, DiMaggio always maintained radical, conspiratorial views that the government had Monroe killed. While those claims are as yet unsubstantiated, they add to the intoxicating cosmology of Yankee politics.

Elsewhere in the parliamentary realm, noted former secretary of state Henry Kissinger is a huge Yankees fan to this day, having seen his first game at the Stadium in 1938. A winner of the Nobel Peace Prize, Kissinger served under Richard Nixon and Gerald Ford in the 1960s and 1970s, pioneering the use of détente in relations with Vietnam and the Soviet Union. “I went to a World Series game in Fenway Park wearing a Yankees jacket,” Kissinger once said. “It was life-threatening.”

By contrast, when Nelson Mandela donned a Yankees jacket and cap at the Stadium in June 1990, reaching another apex on his cathartic Freedom Tour amid the denouement of apartheid in South Africa, he was serenaded by 55,000 rabid fans. “I am a Yankee,” the civil rights campaigner famously said. Duly impressed, Steinbrenner covered the cost of Mandela’s three-day visit, during which more than 1 million people clogged the streets of New York in support. Mandela even has a plaque in Monument Park to this day, a fitting reminder of the team’s broad doctrine.

The Yankees became regular White House guests in the 1990s, upholding the tradition of championship teams visiting the commander in chief. Bill Clinton and Barack Obama hosted the Yankees, who often presented gifts to their distinguished leaders. Hilary once sported the interlocking NY cap, for instance, while Obama received a signed jersey. If nothing else, those quirky connections make for entertaining conversation.

In 2019, the Yankees even fraternised with British royalty, welcoming Prince Harry and Meghan Markle into their clubhouse during the historic London Series. “You guys have beaten next door’s present, by the way,” said Harry, referring to gifts received from the Yankees and Red Sox. Harry threw out the first pitch before Game 1 at the Olympic Stadium, adding another tale to the pinstriped political almanac. 

Finally, even this year, we have seen the Yankees lend their support to civil rights activism. On Opening Day, shortly before Fauci’s first pitch, 75 players and coaches from Washington and New York knelt before the national anthem in a display of solidarity with the Black Lives Matter campaign and associated causes. Since then, notable Yankees players such as Giancarlo Stanton and Aaron Hicks have continued the symbolic act, speaking out against racial inequality.

Of course, Trump is virulently opposed to professional athletes taking a knee, branding it unpatriotic. “It is great that baseball is back,” he said recently during an appearance on the Sean Hannity Show. “I just hope everyone is standing.” Indeed, some believe the defiance of Stanton, Hicks and their teammates contributed to the president’s Yankee-related climbdown. He did not want to be embarrassed in public.

Donald Trump and the New York Yankees – A complicated relationship

Ultimately, Trump’s self-centred brand has expanded to such an unrelatable stratosphere that he now sees association with anything or anyone as innately damaging or undermining. A self-described ‘stable genius,’ Trump is omnipotent and omniscient, at least in his own mind, and no single entity is worthy of equal footing beside him. Not Dr Fauci, and not even those fabled Yankees from the Bronx.

In the mid-2000s, for instance, Trump asked Steinbrenner for the contract to build the new Yankee Stadium, but George demurred. “If I do that,” he said, “it will be Trump Stadium, not Yankee Stadium.” Few people knew The Donald like The Boss, it would appear. Fewer still had the power or bravery to reject Trump, which Steinbrenner did with good reason.

Still, the Trumpian ethos of rampant cynicism and garrulous annihilation has never quite extended to the Yankees. Deep down, Trump has always maintained terrific respect for the organisation, perhaps tinged with a little envy. There was always a vague pinstriped fascination emanating from that gold tower, and it became truly evident when a string of ex-Yankees players appeared on The Celebrity Apprentice. Darryl Strawberry, José Canseco and Johnny Damon all appeared on the show, which provided a window into Trump’s secret tastes. 

Alas, when The Boss died in July 2010, much of that sentiment was expressed for the first time. “George Steinbrenner was a great friend and a true legend,” Trump wrote in a Facebook post. “He understood winning better than anybody. There will never be anyone like him in New York. The country has lost a truly great man.”

Going even further, Trump then released an official statement, waxing lyrical about his loyal friend. “Every detail mattered to him, and the bottom line is that his tenacity worked,” it read. “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 baseball history. 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 will be greatly missed.”

As Trump adopted social media as a direct tool of communication, he often used sites like Facebook and Twitter to lament the Yankees’ divergence from George’s philosophy. The Donald became something of a vessel for Steinbrenner’s enduring conscience, and many Yankees fans shared his views about the team’s decline.