The Dark Truth About Donald Trump’s High School Baseball Past?

In the world of sports, memories can sometimes grow larger than life, and this seems particularly true for former President Donald Trump. Throughout his life, Trump has shared stories of his time as a high school baseball star, often framing himself as a potential professional player. But how much of this narrative holds up under scrutiny?

Trump’s Recollections: A Star in New York Military Academy?

Donald Trump has frequently claimed that he was destined for a career in professional baseball. In his 2004 contribution to The Games Do Count: America’s Best and Brightest on the Power of Sports, Trump recounted his days at the New York Military Academy (NYMA) as a baseball team captain. He proudly recalled hitting a game-winning home run against Cornwall High School in 1964, a moment so significant that it earned him a headline in the local newspaper: "TRUMP HOMERS TO WIN THE GAME."

But the facts don’t seem to fully support this rosy recollection. Extensive searches through local newspapers have failed to uncover any such headline, and records indicate that NYMA didn’t even play against Cornwall High School in 1964.

A Pro Baseball Career at New York Military Academy(NYMA)? The Truth Behind the Claim

Trump has repeatedly stated that he was good enough to play professional baseball, even suggesting that he was scouted by major league teams like the Boston Red Sox and Philadelphia Phillies. His former coach at NYMA, Theodore Dobias, supported this claim, describing Trump as "quite the athlete" who had caught the eye of scouts.

However, it's important to note that while Trump was indeed a solid first baseman, his actual baseball performance appears to have been less extraordinary than his stories suggest. Teammates from his time at NYMA remember him as a competent player, but not necessarily a standout. While Trump was awarded the "Coach’s Award" in 1964, it was an honor more reflective of his dedication and team spirit than his athletic prowess.

Donad Trump in his younger days

The Reality of Trump’s Baseball Abilities

Many of Trump’s classmates remember him as a capable player, particularly on defense, but not someone destined for the big leagues. In fact, some who played alongside him describe his hitting as mediocre. Jim Toomey, Trump’s co-captain, was the one who received the "Most Athletic" title in their senior yearbook, as well as the prestigious Laidlaw Athletic Award, which was given to the school’s best athlete.

Moreover, Trump’s claims of facing off against baseball legend Willie McCovey, who was already an established major leaguer by the time Trump was in high school, seem to be more fiction than fact.

Donald Trump: The Legend vs. Reality

Donald Trump’s retelling of his high school baseball days may have grown with time, as memories often do. While he was certainly an athletic and enthusiastic player, the evidence suggests that his skills, while good, were not extraordinary. The notion that he could have pursued a career in Major League Baseball seems to be more of a personal myth than a reflection of reality.

In the end, like many of us, Trump seems to remember his youth with a bit of embellishment. His tales of baseball glory may not stand up to the facts, but they do offer insight into a man who has always seen himself as destined for greatness, in whatever field he chose to pursue. 

Whether it was on the baseball diamond or in the real estate market, Donald Trump’s self-confidence and competitive spirit have always been his defining traits.

New York Military Academy(NYMA)

In the quest to uncover the truth about Donald Trump’s athletic prowess during his high school years, the answer lies just four miles up the river from the New York Military Academy (NYMA) at the Newburgh Free Library. Within the library’s tall metal filing cabinets, microfilm archives hold the records of numerous now-defunct Hudson Valley newspapers, some dating back to the early 19th century. 

Among these, the Evening News of Newburgh, New York, provided extensive coverage of NYMA during Trump’s time there.

While not every game played by NYMA was documented in the local papers, I was able to find accounts of approximately a quarter of the games from Trump’s sophomore and junior years. Additionally, coverage from opposing teams shed some light on NYMA’s away games during Trump’s senior year.

The first mention of Trump in an NYMA baseball story appeared in 1962, during his sophomore year. The story’s final line reads, “Don Trump made some fine fielding plays for Coach Ralph Petrillo’s NYMA club.” 

In that game, a 4–1 loss to Cheshire, Trump played first base, batted sixth, and went 0 for 3. I found three box scores from his sophomore year, where Trump went 1 for 10 at the plate. Given that NYMA played only a dozen or so games per season, Trump’s entire high school baseball career likely spanned between 30 and 40 games.

While it may seem unfair to draw conclusions from such a limited sample size, the box scores indicate that Trump’s .100 batting average in his sophomore year was the lowest among the five players who had at least eight at-bats. 

In his junior year, Trump’s batting average improved slightly to .200, but the team as a whole struggled, managing just 11 hits over three games. By his senior year, four of Trump’s teammates had outperformed him in terms of hits.

To gain further insight, I consulted Keith Law, a senior baseball writer for The Athletic and author of The Inside Game. Law, who has experience assessing high school players for the Toronto Blue Jays, didn’t mince words: “There’s no chance,” he said, when asked if Trump’s numbers suggested he was a pro prospect. “You don’t hit .138 for a small, cold-weather high school playing weak competition and expect to be recruited by Division I programs, let alone pro teams. It’s laughable. He couldn’t hit—that’s pretty clear.”

The sparse coverage of Trump in the local papers is telling. Even in small schools like NYMA, standout athletes often received significant attention in the press. During the same era, a pair of star players from nearby Storm King regularly garnered extensive write-ups. 

Bo Gill, the longtime sports editor of the Evening News, made it his business to know about the best local players and give them due recognition. If Trump had truly excelled, it’s likely there would have been at least one story dedicated to him in his hometown papers.

Yet, there’s no mention of Trump in the local papers during his senior year, when he was allegedly on the radar of at least two professional teams. Both the Red Sox and the Phillies were unable to confirm or deny the claims made by Trump’s coach, Theodore Dobias, due to a lack of scouting records from 1964. 

However, Law noted that it’s unlikely either team would have sent scouts to evaluate a first baseman from a small private school playing against weak competition.

Among Trump’s former teammates, only Joe Kinego recalls scouts attending their games. The other six teammates I spoke with couldn’t remember anyone being scouted. Dick Guido, a former teammate, expressed skepticism: “I think we had a pretty good club back then, but I’d be surprised if we were on the radar of a Major League Baseball team.”

Even more dubious is the idea that Trump’s .138 batting average would have attracted professional scouts. “I’ve never heard of a legitimate high school prospect in this era who hit less than about .275,” Law said. “It’s almost unthinkable. Nobody is scouting that guy.”

It’s important to note that Trump has never claimed to have been scouted, only that he attended a tryout and could have gone pro. The scouting claim was made by Dobias, who may have been as invested in embellishing Trump’s origin story as Trump himself. 

After all, Dobias was a legend at NYMA, having entered the academy at 16, fought in the U.S. Army during World War II, and returned to NYMA to graduate and later become a major. Dobias spent his life at the academy, raising his family there and eventually passing away on the grounds. 

According to Trump’s former teammate, Sandy McIntosh, who wrote about Trump in the New York Daily News, Dobias was “the academy’s unofficial PR man” and “contributed to the Trump myth.”

The bond between Trump and Dobias was strong. Gwenda Blair, author of The Trumps, noted that Dobias took a particular interest in Trump’s development, even making him the “unofficial assistant baseball coach” during his senior year. However, it’s worth mentioning that Dobias was not the varsity baseball coach during Trump’s time at NYMA—Ralph Petrillo and Michael McCann held that position—so Dobias couldn’t have given Trump such a title.

On the 127-acre NYMA campus in Cornwall, New York, there’s little evidence of Trump’s time there. No buildings are named after the school’s most famous alumnus, nor is Trump mentioned on the NYMA website. However, his picture is framed in a hallway in the main building, part of a school hall of fame. 

There’s also a plaque beside a classroom door, noting Trump’s donation to refurbish the room in honor of his parents. His name is inscribed among the 2005 inductees to the academy’s sporting hall of fame. In 2001, Trump returned to give the academy’s commencement address, arriving by helicopter with a model girlfriend, bragging about buying the Empire State Building, and urging graduates to “think big.”

Though the dorm Trump lived in has been condemned, the academy’s billionaire owner, Vincent Mo, refuses to tear it down, as visitors enjoy taking selfies in front of it.

Trump’s baseball career effectively ended at NYMA. He didn’t play baseball at Fordham University or the University of Pennsylvania, where he transferred his junior year. Instead, he joined the squash team at Fordham and never played hardball again.

Trump’s connection to baseball didn’t end entirely, though. He was close with the late New York Yankees owner George Steinbrenner and even threw out a first pitch at Yankee Stadium before a game against the Red Sox in 2006. Trump’s ties with the Yankees ran deep, to the point that he reportedly considered longtime team president Randy Levine for a White House chief of staff position.

Yet, despite his deep connection to the sport, Trump became the first president since Teddy Roosevelt not to throw out a first pitch at a professional baseball game while in office, ending a 110-year tradition. In that respect, at least, Trump has made baseball history.