Growing up in the small town of Mahopac, New York, Jeff Pearlman always knew that he wanted to be a journalist. Although he knew his career path, not even Pearlman knew how successful he’d become. Pearlam has had nine of his books appear on the New York Times Best Sellers list, a T.V. show based on one of his books, a successful podcast, and more.

But all this success is thanks to a little bit of attention from his high school’s cheer squad.

“I wrote a story for the student newspaper called, ‘Cheerleading: Sport or Activity?’ And I wrote it and decided cheerleading isn’t a sport, it was just an activity. When the paper came out, all the cheerleaders were really mad at me, and they all surrounded me in the lunchroom. They were yelling at me, ‘How could you write this?’ It was all of the really pretty girls who never paid attention to me, all surrounding me. And I was like, ‘this is the greatest thing ever.’ You actually get attention for writing. That was my start,’’ Pearlman said.

Pearlman was very successful early on in his journalism career. He wrote for a local paper called The Putnam Trader which he credits for what led him to write for the student newspaper at the University of Delaware. His time writing at Delaware got off to a rocky start. Pearlman was kicked off of The Review as a freshman, but later reinstated after much convincing.

After Pearlman graduated, his career didn’t get off to a hot start. Pearlman was hired by The Tennessean to review local food and music in Nashville, Tennessee. This may seem like a big break for a young writer, but it wasn’t for Pearlman. His attitude and overall ability held him back.

“I was super cocky, and I thought I was the best. I thought I was destined for greatness, but I sucked. I made mistake after mistake after mistake. I never understood assignments. I got names misspelled. Names of songs and music reviews were wrong,” he said.

Pearlman and the editors of the The Tennessean quickly realized that this wasn’t his calling. He was then assigned a role covering the local police. This allowed Pearlman to take a more simple approach to writing, and get back to the basics that started his success.

“Don’t worry about being a fancy writer. Don’t worry about dazzling us. Just get the facts right: who, what, where, when, how, and why. That changed my career. It actually changed my career and the way I started thinking about writing,” he said. “At some point I realized you might be the best writer at your high school newspaper, you might show up to college and you might be the best writer, but if you can’t report and you can’t get facts right and you’re not good at details, it doesn’t matter.”

Even though his time with The Tennessean taught him a lot, Pearlman couldn’t get the hang of police, food, or music. This led to the end of Pearlman’s two-year stint with The Tennessean. But Pearlman’s career was about to significantly change.

In 1996 Pearlman landed his dream job: writing for Sports Illustrated.

“It was like some guy dreamed of playing for the Yankees or some guy dreamed of being a star on Broadway. That was the equivalent for me getting hired at Sports Illustrated,” Pearlman said.

Pearlman was hired as a baseball writer, where he got to travel the country and interview the stars of the MLB. This also came as a great learning experience for Pearlman. He spent time in the office surrounded by some of the best sports writers in the world. The then-22-year-old Pearlman was able to learn from the likes of Tom Verducci, Tim Kurkjian, and others.

Pearlman’s most notable work from his time at Sports Illustrated is his interview with former Atlanta Braves closer, John Rocker. Pearlman spent a day in Atlanta with Rocker and his story was able to show Rocker’s racist, homophobic and ethnocentric beliefs to the world. Many former teammates had advocated against Rocker, but Pearlman was able to expose Rocker’s disturbing character on a national level.

“I’m not doing it to debate him. I’m there to listen to him and learn from it. That’s one of the things in journalism that you learn to overcome. You have to be a really good listener. You have to set aside any of your personal beliefs or morals and just listen to the person. And when you hate what they say, it can be particularly challenging,” Pearlman said.

Pearlman received backlash from Rocker himself after the article was published. Rocker threatened Pearlman multiple times and claimed that the article “misrepresented” him.

Five years later, while covering the 2001 World Series, Pearlman’s career was about to take another turn. He was in the press box for game 4 at Yankee Stadium, when he had terrible stomach pains. Since he wasn’t writing about that game, he left and took the subway to his then girlfriend’s (now wife’s) apartment. It was there Pearlman watched Derek Jeter hit a walk-off home run to beat the Diamondbacks 4-3. Oddly, he wasn’t upset about missing a classic ending and took it as a sign.

“It was an all-time great game and I’m on my girlfriend’s couch. I know after the game I’m not going to have to interview players. I know I’m not going to be hit by some cameramen and cameras in a crowded locker room. I know I’m not going to hear the cliches. I was so happy to be (at my girlfriend’s apartment). I had a realization ‘if you’re happy not to be at one of the great World Series games of all time, you probably shouldn’t be covering baseball anymore,’” Pearlman said.

This practically ended Pearlman’s time at Sports Illustrated, but that is where he started having an interest in writing books.

Since that revelation, Pearlman has written nine books that have appeared on the New York Times Best Sellers list. From Bo Jackson to the 1986 New York Mets, Pearlman has a long list of successful works, but one seems to stick out to Pearlman.

“Showtime”, a book about the 1980’s Lakers was an immediate success. It was so successful that HBO turned it into the T.V. series, “Winning Time”. “Winning Time” featured stars like Adrien Brody, John C. Reilly, and Sally Field. Pearlman was listed as a producer on both seasons of the show.

“It’s amazing. It was like summer camp and a bar mitzvah and a wedding all kind of merged into one. It almost feels like it never happened. I’m sitting in my little living room and we had the entire cast here for a party, and we were all watching one of the episodes, and it was like, here’s this joyful community of actors and young people and older people all coming together,” Pearlman said.

In a career full of success Pearlman hasn’t stayed complacent. He is set to release a biography of the life of Tupac Shakur titled, “Only God Can Judge Me: The Many Lives of Tupac Shakur” in late October of 2025.

Although it may seem cliche, the secret to Pearlman’s success is loving what he does.

“I just like the buzz of writing. I really do, even as much as I hate writing, I love writing. I’m really passionate about writing,” Pearlman said.