A balanced history of Donald Trump and the New York Yankees

In the past 110 years, the United States has elected 19 Presidents. All of them - except one - have thrown out the ceremonial first pitch at a Major League Baseball game. As in most cases, Donald Trump is the outlier, and his recent exploits in this regard have been typically absurd.

When Dr Anthony Fauci, the public face of America’s coronavirus response, threw out the first pitch at Nationals Park in Washington, D.C., on Opening Day this year, Trump plumbed the depths of alternative facts to forge his own moment in the baseball sun. His stunt backfired remarkably, however, adding another bizarre chapter to a most unusual presidency.

“Randy Levine is a great friend of mine from the Yankees,” Trump said from a White House lectern on 23rd July. “And he has asked me to throw out the first pitch. I think I’m doing that on August 15th at Yankee Stadium.”

With that, a hyper-liberal shitstorm engulfed Yankees Twitter as fans protested the apparent invitation. Amid our cancel culture zeitgeist, the Yankees could barely have chosen a more controversial figure to spearhead such a needless event. It seemed preposterous and, ultimately, it was.

You see, the Yankees did not formally invite Donald Trump to throw out the first pitch on that day. Or any other day, in fact. According to the New York Times, Yankees officials were dumbfounded by the president’s claim. He seemed to have plucked a random date out of thin air, and it just happened to coincide with a game at Yankee Stadium. As ever, confusion reigned supreme.

Ultimately, Trump was furious that Fauci, not Trump, was asked to throw the Nationals’ first pitch. The president is locked in a passive-aggressive, narcissistic bitchfight with Fauci, whose approval ratings keep Donald awake at night. Trump hates to be outdone, and Fauci represents a consistent risk in that area. Hence Trump’s phantom Yankees flirtation. Hence a misguided use of presidential privilege that never worked out. Hence chaos.

Following the aforementioned press conference, Trump had Oval Office aides scramble to contact the Yankees, hastily trying to trigger a longstanding suggestion – not an official invitation - made by Levine regarding a potential first pitch. A deal could not be agreed, however, leaving the president in a bind.

Indeed, just three days after his apocryphal pronouncement, Trump was forced to backtrack and downplay the whole first pitch escapade. In a style befitting the broken satire of our time, the president was forced to cancel an event that only existed in his own head. When it came, the meandering tweet was predictably dramatic.

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. 


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 14th 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.


When star shortstop Derek Jeter suffered a nasty injury in 2012, Trump became something of an impromptu beat writer, tweeting random updates about the captain’s rehabilitation. Donald also famously intervened in one of the many spats between Jeter and Alex Rodriguez, his nemesis who awkwardly became a teammate.


Accordingly, there has always been an awkward epistemic distance between Trump and the Yankees. At once, he has been a passionate fan and a fearless critic, a defender of the dynasty but also a lamenter of the team’s modern approach. Ultimately, though, one wonders whether Donald’s relationship with the franchise is rooted in jealousy. The Yankees are the only thing in New York that Trump has never managed to control, and that affords the organisation a morbid curiosity in his mind.

A-Rod, Jeter and Hideki Matsui – Inside Trump’s Yankees ‘curse’

Just as Steinbrenner invited famous people to his Yankee Stadium suite to watch games, keen for an ego massage between pitches, Trump has always tried to infiltrate the inner sanctum of professional sports, seeing it as one last focus of hyper-attention that does not revolve around him. Historically, Donald has attempted to cultivate high-profile friendships with sports stars to satisfy that itch, but those efforts have often backfired.

For example, the aforementioned Jeter and A-Rod bought apartments in Trump buildings during their days in pinstripes. Hideki Matsui did, too. When Jeter and A-Rod sold their bachelor pads, Trump peddled tongue-in-cheek myths about a curse condemning them to poor play or misfortune thereafter. Few people stopped to take notice, however.

Has Donald Trump ever tried to buy the Yankees? And will he bid in the future?

Naturally, Trump has often been linked with rumoured interest in purchasing the Yankees. After all, the guy is an obvious fan, plus he has $2.1 billion in the bank. Oh, and he has bought just about everything else that has ever interested him - from hotels, casinos and golf courses to airlines, private jets and football teams; from Miss Universe pageants, universities and helicopters to television shows, fashion labels and political endorsements. 

Has Trump ever tried to buy the Yankees? Did he ever make an offer to Steinbrenner after sinking a few beers? Well, factual evidence is hard to unearth in this matter, but in true Trumpian fashion, that should not deter us from telling a good story. Donald probably wanted to own the Yankees more than he wanted to become president, so we should probably explore the incessant rumours in greater detail.

“In the early 1980s, Trump had flirted with team ownership several times,” write Michael Kranish and Marc Fisher in Trump Revealed, their 2017 biography of the president. “He unsuccessfully bid $20 million for the New York Mets, and when the Cleveland Indians were up for sale, Trump went as high as $34 million. That deal fell through over Trump’s reluctance to promise to keep the team in Cleveland.”

According to Kranish and Fisher, Trump also held exploratory talks about buying the Baltimore Colts, but they died when the team moved to Indianapolis. That is when the Generals proposition came up, linking directly to Trump’s meeting Steinbrenner and building a powerful bond. Furthermore, in 2011, Fred Wilpon approached Trump about another potential run at buying the Mets, but Donald declined, perhaps eyeing his long-term involvement in politics.

In 2015, Colin Cowherd of Fox Sports asked Trump which sports team he would like to own, if he could choose any. Donald picked the Yankees, of course, with a cursory nod to the Dallas Cowboys and their impressive monetary value. Accordingly, there is almost a mournful sense of failure – crafted by simple deduction since he gets everything else he wants - surrounding Trump’s chronic inability to own the Yankees. It is fascinating to watch.

While a formal Trump bid for the Yankees has never been reported, his name is often uttered on forums and in gossip columns as a logical suitor should the Steinbrenner family ever wish to sell the franchise. Certainly, it would rank among the most powerful post-presidency transitions of all-time if he were to pursue the team, say, next year, but I do not think that will ever happen.

The Steinbrenners are wedded to the idea of eternal control, and they are unlikely to risk the public relations meltdown of negotiating with Trump in any event. That boat appears to have sailed, thankfully, but there is an alternate universe out there in which the new Yankee Stadium has gold cladding and where the hometown team wears glittering pinstripes. I will leave that one to the dystopian novelists, however. A hellish imagination is required to bring that particular tale to life.

Johnny Damon, Paul O’Neill and the Yankees who have endorsed Trump

Whether he occupies the ownership suite or not, Trump has enjoyed support from prominent ex-Yankees during his rise to power. In 2016, for instance, the aforementioned Johnny Damon gave an introductory speech at a Trump rally in Florida, a few days before the general election. “People wonder why I like Donald Trump,” said Damon. “I actually love the guy. Why? Because he likes winners, he likes to win, he likes everything to be great, not just for him but for everybody. He wants to make America great again.”

Seated on the front row, within touching distance of Trump, Damon waved a MAGA placard. Trump thanked him for the kind introduction, branding Damon the ‘ultimate champion and winner.’ Damon has repeatedly supported Trump throughout his presidency, offering soundbites of support and speaking to the human behind the controversial dogma.

Similarly, Paul O’Neill, one of the most beloved Yankees of modern times, has publicly endorsed Trump in the past. O’Neill also attended a rally in 2016, and Trump gushed like a teenage fanboy while pointing him out in the crowd. “Now that I have Paul O’Neill’s endorsement, I know I’m going to win Ohio,” said Trump. “I love you! Thank you!”

Meanwhile, Trump continues to curate a strong relationship with the Steinbrenner family. In 2015, Donald teamed with Hank Steinbrenner on his Hank’s Yanks initiative to enrich youth baseball in the Bronx. Trump hosted a golf tournament at one of his courses to raise funds for the endeavour, speaking reverentially of his respect for George’s progeny.

When Hank died in April 2020, Trump tweeted his condolences to the Steinbrenner family, calling Hank a friend. Once again, in a world where Trump is increasingly insular, and where he more routinely makes enemies than allies, that is an interesting concept with far-reaching connotations for the Yankees’ organisation.

Why Trump gave the Presidential Medal of Freedom to Babe Ruth and Mariano Rivera

Contrary to conventional wisdom, since assuming the Oval Office in January 2017, Trump’s interactions with the Yankees have actually increased, rather than tailing off. That seems unusual for a president, but then again, most things are in the world of Donald Trump.

In November 2018, Trump gave the Presidential Medal of Freedom – posthumously, of course - to Babe Ruth, the ultimate Yankees icon. “He raised money and raised hell,” said The Donald of The Great Bambino. “Maybe that’s why it’s taken so long for him to get this award. He should have gotten it a long time ago. I said, ‘Babe Ruth hasn’t gotten it?’ We took care of that real fast.”

A month later, more internet chatter linked Trump to the Yankees. On that occasion, Trump was rumoured to be considering Randy Levine, the Bombers’ aforementioned team president, for his vacant chief of staff position. “I have great respect for the president but I’m very happy being president of the Yankees,” Levine told Fox News, quashing the connection. Nevertheless, he remains a Trump supporter, hence the president’s wild attempts to wangle a first pitch gig at Yankee Stadium. 

Somewhat bizarrely, Trump has also cosied up to Mariano Rivera, the Yankees’ legendary closer of yesteryear, during his time in office. Rivera has been part of Trump’s Commission on Combating Drug Addiction and the Opioid Crisis since 2017, while he, too, earned the Presidential Medal of Freedom in 2019. Lonn Trost and Joe Torre - high-profile members of the Yankees’ extended family - attended the White House ceremony, which descended into corny reminiscence.

“The Sandman,” Trump said of Rivera as the Metallica ballad played, just as it did when Mariano entered games at Yankee Stadium. “My life asked, ‘Why ‘The Sandman?’’ I said, ‘Because he put the batter to sleep, right?’ ‘The sandman.’ A lot of people don’t know that, but the Yankee fans know that. We’ve watched it for a long time.”

In the strangest twist yet, Rivera was a presidential guest on Opening Day this year, when Trump responded to Fauci’s first pitch with the mythical engagement of his own. Mariano and Donald played catch on the White House lawn, mingling with little leaguers in a contrived publicity call of minimal utility.

Like Damon and O’Neill, Rivera has placed on record his respect and admiration for Trump. By all accounts, the pair enjoyed a friendship before Donald took office, and Mariano has been uncharacteristically bullish on his White House connections. Indeed, for such an immaculate baseball genius – the game’s first and only unanimous Hall of Fame inductee, no less – to stump for Trump represents a huge departure from our classic interpretations. Many Yankees fans struggle to square that circle.

Why did Trump call A-Rod for help with the coronavirus pandemic?

While Rivera’s mingling with Trump is uncomfortable for some, A-Rod’s recent re-emergence onto the president’s approved list of contacts is nothing short of absurd. In March, back at the start of the current coronavirus pandemic, Trump reportedly called Rodriguez – his former nuisance tenant – for his input on responding to the global health emergency. Quite why, nobody knows, but these things happen almost daily in the Trump White House.

Sure, Rodriguez has crafted a remarkable renaissance after seeing his reputation sullied by steroid suspensions and legal nightmares. A-Rod has been transformed into a likeable media personality and a skilled businessman, winning new fans despite his controversial past. However, for the president to seek help from a baseball player with regard to an infectious disease, when Dr Fauci is literally on the payroll, is ridiculous. Yes, A-Rod has injected a lot of substances in his life, but I do not think bleach is one of them.


The call was reported by John Santucci of ABC News, but Trump denied the claims, categorising them as fake news. Nevertheless, multiple sources corroborated Santucci’s report, which illustrated yet again how Trump is willing to use the presidency to raise his own profile and boost his own relationships with people he secretly admires.

Will Trump throw out a first pitch for the Yankees in 2020? And why does it matter?

So, when all is said and done, will Donald Trump throw out a first pitch before his presidency expires? Will the Yankees invite him to conduct the ceremony at some point later in the 2020 season? Does it even matter, and why are we focusing on such trivial concerns?

Ultimately, we do not know for sure. One would rank the odds as unlikely given the backlash to Trump’s phantom announcement, but we can never be surprised by this guy anymore.

Personally, as a left-leaning centrist, I grimace dully at the notion of Trump getting cosy with the Yankees. However, by the same token, I also view the super-woke cancel culture outrage as an entirely disproportionate reaction.

In this hypersensitive age, we are conditioned to think things can only be sublimely stupendous or catastrophically disastrous. There is no middle ground, resulting in a fractured vacuum where optics obfuscate action. In my mind, Trump throwing out a first pitch would be neither brilliant nor disgraceful. It would simply be the continuation of a vaunted tradition passed down through multiple generations. 

Of course, I understand why people are angry at the merest hint of Trump sympathy within the Yankees organisation – real, imagined or otherwise. Trump has said and done some hideous things. By any measure, he ranks among the most illiterate, incompetent and incomprehensible human beings to marshal a desk in the Oval Office. I loathe much of his ethos, but I also see fit to defend my favourite baseball team from being cancelled by association – an association it does not publicly encourage, and an association it has rarely sought to formalise. We have to see the world in more dimensions, and this binary madness must stop.

That Trump is the most divisive person ever to occupy the White House is now baked into our cultural zeitgeist, whether the charge is accurate or not. As such, from among the contingent that detests him, Trump receives unprecedented levels of vitriol. Apparently, that extends to sporting triviality, because his potential presence at Yankee Stadium elicited protests quite unlike those for any President ever to grasp a baseball.

While the woke meltdown is a bit extreme, it is inappropriate for the Yankees to get involved with the president this close to a general election, regardless of your political bent.

Trump may well have fabricated his readiness to throw out a ceremonial first pitch at Yankee Stadium, but his ability to do so, and for it to be so thoroughly believable, speaks to a longstanding relationship with the team that is a little too familiar for many people to bear. It would be ideal to receive some clarity on that relationship, a peak behind the hood, but in the whacky world of Donald Trump, nothing is ever that easy. Nothing is ever as it initially seems.

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