The year is 1982 in a hilly, wooded, lake-scattered hamlet in Putnam County of Mahopac, NY, with a population of about 9,000.
Ten-year-old Jeff Pearlman is one of these 9,000.
It’s a Saturday morning. The Pearlman household has received two newspapers: The New York Times and The Reporter Dispatch. Jeff’s father is assigned to read the news section, his brother the business section, and his mother the features section. Jeff takes the sports section.
“[Sports] was the only section my mom would allow anyone to take into the bathroom…I would sit there in the bathroom poring over it, studying the pictures, the words, the whole thing,” Jeff said.
Of course, the bathroom was not the only place young Jeff did his reading. He was a frequent visitor to the local library, where he read the latest editions of Sports Illustrated, a magazine his non-sports-loving parents refused to subscribe to.
Flash forward to the present day, and it is safe to say that all the reading 10-year-old Jeff did has paid off. As a New York Times best-selling author of 11 books — including one that was made into an HBO original series — and with stints at Sports Illustrated, Newsday, and ESPN.com, Jeff’s notoriety has spread far beyond Mahopac — where it all began.
Why Jeff Pearlman Started Writing
But what led to Jeff wanting to write about sports? Just like nearly every kid growing up, it was for one reason: to be noticed.
When Jeff began writing for his high school newspaper, that’s when he started to get his name out there.
“You start writing, people start paying attention to you, and they listen to you,” Jeff said. “You do a report card on the basketball team and the kids get mad at you, you critique the cheerleading team and the cheerleaders pay attention…there was this buzz about it.”
Jeff’s fearless approach to stories followed him to the University of Delaware. He immediately began writing for UD’s The Review, the university’s independent, student-run newspaper. While he admits that some of his early writing may have been subpar, his chutzpah never wavered, no matter the number of punches he took.
“You have to get smacked around a lot to learn what it is to get smacked around a lot…getting punished, getting demoted, getting embarrassed, all those things, you need them to grow as a journalist, and you get a lot of that at college,” Jeff said.
However, there is one critical mistake Jeff cautions aspiring sports journalists to avoid: making their work about themselves. After all, one of the most beautiful things about being a journalist is having the privilege to observe and listen to other people’s stories.
Jeff has more advice that can be universally applied beyond journalism: be adaptable. Jeff, whose work was expressly for print media throughout much of his career, has since expanded his voice into the YouTube and TikTok realm.
“When I was at Sports Illustrated, there were a lot of writers who did not want to write for the web, they steadfastly refused…almost all of those writers are out of the business,” Jeff said.
Does he particularly like taking his work to social media to produce content? No.
But he didn’t see it as a choice.
“I don’t want to do this sh*t, like not really…you either adapt or you fade away, and I feel like at 53 years old, I’m too young to fade away,” Jeff said.
Jeff’s Life Outside of Writing
But part of not fading away requires taking a break from the screen. For Jeff, he makes sure to give himself time outside of the demanding sports media realm. This might be going for walks with his dog Poppy near his scenic Southern California home, listening to music (a true child of the 80s, Jeff’s an avid Hall & Oates fan), or playing pickup basketball.
Jeff Pearlman is by no means an arrogant man. The only category in which he comes somewhat close to having an overdose of confidence is his pump fake. He learned from his roommate during his time at UD, legend has it that it is nearly un-guardable.
“I have one of the great pump fakes of all time…I’d be smokin’ Fairfield intramurals right now,” Jeff joked.
As much as the best-selling author likes to hoop, his favorite thing to do in his free time is be with his family. Jeff is a husband to Catherine and father to Casey and Emmett. Although he has garnered a myriad of accomplishments throughout his career, Jeff considers his biggest win the fact that he was a steady presence for his kids growing up.
“I was around for everything…I was my kids’ Class Mom one year, I coached youth sports all the time, every ballet recital…my greatest pleasure and the thing I’m most proud of…I was a very present dad,” said Jeff.
Ultimately, Jeff Pearlman is a man of many things: a Hall & Oates roadie (not true), a pro pickup basketball player (still not true, but closer), a wildly successful author, and a devoted family man (okay, both true). His exceptional sports knowledge and his witty sense of humor stand out for those who are lucky enough to meet him.
But be warned.
To anyone unlucky enough to find themselves having to guard Jeff on the basketball court, two words of advice: Don’t jump!
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