The conversation began with nostalgia—fitting start for a journalist whose career thrives on it. Jeff Pearlman, the sports writer behind bestsellers like The Bad Guys Won and Showtime, settled in to discuss his path that led him from food and fashion writing to becoming one of America’s most compelling chroniclers of sports history.
Pearlman has met and interviewed many Hall of Fame athletes. However, the only encounter that ever made him nervous was with his childhood hero, Ken Griffey Sr—the Yankees outfielder and father of Ken Griffey Jr.
“I literally have a picture of Ken Griffey Sr. hanging up on my wall here,” he admitted with a laugh. Years later, as a baseball writer covering the Reds, Pearlman got to meet his childhood idol. Despite interviewing sports legends without a tremor, Griffey was different. “I built him up in my head all those years.”
But the most influential person in Pearlman’s life was his father, Stanley. When Jeff was 14, his dad self-published a business book titled Conquering the Corporate Career. The family would visit their local Waldenbooks where they’d casually move copies of the book from the back business section to the front bestseller display.
“My dad having written that book… I don’t think he understood until later how big of an impact that had on me,” Pearlman reflected.
Pearlman’s entry into journalism was rocky to say the least. He was covering food and fashion for the Nashville Tennessean, making $26,000 a year. “I know nothing about either,” he laughs. “I still dress like a slob. I can’t cook. I just burned salmon like two hours ago.”
His editor at the Tennessean gave him life changing career advice: Stop trying to dazzle with fancy writing. Just get who, what, where, when, why, and how. Get the facts.
“I was always writing around my lack of information,” Pearlman admits. “I was trying to be fancy, but I didn’t have the details. I just had the flare, and anyone can write with flare. Getting details is hard.”
As a kid, Pearlman was vocal to his mother about one day writing for Sports Illustrated. There was no reality for that to happen; if anything, it felt like a pipedream.
His big break came through his creativity, maybe something he learned from his father.
As a college junior, he applied early for the NBA draft as a prank, despite only playing intramural basketball. The NBA actually processed his application. He wrote about the experience, sent it to SI, and they published it. A few months later, at 24, he was hired.
“I always thought I would get to SI at like 35 or 40,” he said. “It just seemed like something you did as an adult.”
Pearlman developed an unusual strategy. Working four days a week, he’d come in on his off days with the ADA directory—a phone book listing every college in America with media director contacts. “I would go A through Z—calling the different schools one by one, Abilene Christian, Adelphi, and so forth.”
He’d phone the schools in search of interesting stories, not your typical achievements. “It has to be more unique than that. Like the three-foot-seven gymnast, or the point guard from Uganda who doesn’t speak English.”
Before long, “I was coming into meetings pitching like these crazy stories and the editors not knowing where I got ’em, but knowing I came with a lot of stories.”
Pearlman hadn’t really considered writing books until a colleague at SI, John Wertheim, wrote one about Venus and Serena Williams. An agent, Susan Reed, reached out and thought a story about the 1986 Mets could be a great book – and he agreed.
Wertheim shared his writing wisdom: “Just view every chapter as a long feature. It keeps it more manageable in your head.”
The book made the bestseller list. “I certainly didn’t expect it, but it was cool. Then, I really liked the idea of books. It’s hard, but I enjoy the solitude of it all, I guess.”
Pearlman’s journey into social media started with defiance. He had his share of disputes with critics on Twitter. His son begged him not to join TikTok. “I’m like, I’m going on TikTok. He’s like, ‘Don’t do TikTok.’ I’m like, ‘I’m gonna do it.’ He’s like, ‘Don’t talk politics, don’t use filters.’ I was like, ‘Well, one of the two, I don’t use filters.'”
He built a sizable following, then 3.0 Labs approached him about a YouTube show. His response? “Nobody’s gonna care. There’s a million people on YouTube telling stories. I’m not famous or anything. Like, why would anyone care?”
The show, Pressbox Chronicles, is where Pearlman brings storytelling to life—and it’s blown up on the internet. It’s the type of stories he was pitching as a 24 year-old at Sports Illustrated. He tells the tragic story of the former Astros ace, J.R. Richard. How an injury derailed the phenom that once was Mark Fidrych. The insane story about the 1988 Miami Heat expansion team. How steroid usage led to brain cancer and deteriorated Lyle Alzado. You get the picture.
But the 9/11 story about Tyler Ugolin, a Columbia basketball player who died in the towers, still moves him. Just days after the attacks, Pearlman searched for athletes affected and found Ugolyn’s name.
“I reached out and got his dad on the phone. This was probably three or four days after this happened. So this was not a comfortable phone call.” Victor Ugolyn initially declined, but called back using star-69: “He’s like, ‘What if I just tell you about my son? I don’t know if I want you to write, but what if I just tell you?’ We probably talked for 40 minutes.”
What changed Victor’s mind? “I think more than anything, you want people to know who your son was. Here’s a guy who seems sincere, who’s genuinely interested. There’s nothing scandalous about what I was doing. And if he didn’t want to talk, there was zero pressure coming from me.”
They’ve remained close friends ever since.
The supernatural footnote came years later. Working on a story at Penn State, Pearlman went inside a packed coffee shop. “I go downstairs. There’s one table with a chair, available. That’s it.” He asked the woman at the table if he could sit. They started talking.
Pearlman asked, as he often does when meeting strangers, where they are from.
“Ridgefield, Connecticut,” she replied.
“Oh, I did a story about a basketball player who died from Ridgefield.”
“Sports Illustrated?”
“I said yeah. And she goes, ‘Tyler Ugolin.’ I said yeah. She responds, ‘Tyler was my high school boyfriend.’”
One chair. A coffee shop he wasn’t supposed to be in. Tyler’s high school girlfriend.
“I’m not spiritual, but his dad has always said he sees butterflies or he sees his uniform number and he feels something… So in that moment, I definitely felt something.”
The subtitle for Pressbox Chronicles: The show where a cranky middle-aged sports writer who has seen it all takes you behind the scenes and into the stories. Now, he’s taking the show on the road to Los Angeles, Philadelphia, New York City, and Dallas in January. Pearlman will be sharing these stories in a live and interactive format where you can hear fascinating stories and ask questions.
As we were winding down our conversation, I asked Pearlman if he’d vote Barry Bonds into the Hall of Fame—if he had a vote of course.
“I used to be a hard no for anyone who cheated. I’ve changed because David Ortiz, Mike Piazza, and Jeff Bagwell are in. I have zero doubt that those guys used. I feel like they’re in because they were nice and agreeable people. To me, that’s not legit. So if we’re gonna let the cheaters in, you have to let Bonds and Clemens in.”