#119 Jeff Pearlman: The Art of Storytelling
Jeff Pearlman is a New York Times bestselling author and one of America's most compelling sports writers, known for his meticulous reporting and ability to bring readers inside the locker rooms and lives of sports' most fascinating figures. He spent years as a writer for Sports Illustrated, where he famously broke the John Rocker story and honed his craft of finding extraordinary stories in unexpected places. Pearlman has authored numerous bestsellers including "The Bad Guys Won" about the 1986 Mets, "Showtime" about the Lakers dynasty which became an HBO series, "Boys Will Be Boys" about the Dallas Cowboys, and books on Bo Jackson, Walter Payton, Brett Favre, and Tupac Shakur—the latter requiring interviews with 650 sources. His YouTube show "Press Box Chronicles" has become a viral sensation, with millions tuning in to hear him share nostalgic deep dives into sports history's most memorable moments, characters, and forgotten stories. Today, Jeff continues to prove that great storytelling is built on one simple principle: getting the details right and treating people with kindness along the way.
What We Discuss:
The power of details in storytelling - Why "taking the little and making it big" transformed Jeff's career, and how getting the facts matters more than fancy writing in today's 22-second video clip world
Building a career on kindness and relationships - How treating people with grace opened doors throughout Jeff's journey, from his father's lesson about never talking trash to why your network remembers how you made them feel
The mistakes that shaped his success - From asking a chef about cannibalism to getting his "ass kicked" on Delaware's track team, Jeff shares the failures and humbling moments that became his most important teachers
Balancing career ambition with being present as a parent - Why Jeff never missed a single moment with his kids for a TV game, his thoughts on the "hashtag girl dad" phenomenon, and parenting wisdom from his wife Catherine (who donated a kidney to a stranger)
The unlikely rise of Press Box Chronicles - How a writer who thought "nobody's gonna watch this" built a viral YouTube show powered by nostalgia, and why choosing projects that hold your interest for two years matters more than chasing money
Show Notes: Jeff Pearlman Interview
[0:00-5:00] Introduction & Childhood Heroes
Jeff's childhood hero: Ken Griffey Sr. and the picture still hanging on his wall
Gary Templeton and the moment he "had me at hello"
Meeting Ken Griffey Sr. as an adult journalist and getting starstruck
Rethinking Darryl Strawberry's legacy with compassion and perspective
[5:00-15:00] The Father's Blueprint
Stanley Pearlman's 1986 self-published book "Conquering the Corporate Career"
The Waldenbooks guerrilla marketing strategy: moving books to the bestseller section
Creating fake publicists David Kohlberg and Arthur Haviland (the Trump/John Barron parallel)
The most important lesson: his father's superpower of never talking trash about anyone
The 1985 moment that shaped Jeff's approach to treating people with grace
[15:00-25:00] The Unlikely Path to Journalism
Why Jeff didn't get into Penn State's main campus
Walking onto Delaware's track team and "getting my ass kicked over and over"
Why failure and humiliation became "one of the most important experiences of my life"
First real job: Food and fashion writer at Nashville Tennessean making $26,000/year
The cannibalism question that should have gotten him fired
[25:00-35:00] Breaking Into Sports Illustrated
The childhood dream: "I'm gonna write for Sports Illustrated" (said with certainty, not hope)
The NBA draft application prank that became his first SI article
Getting hired at age 24: "I always thought I would get to SI at like 35 or 40"
The competitive environment and his unique hustle strategy
Calling every college in America alphabetically looking for the "three foot seven gymnast"
[35:00-45:00] The Turning Point: Learning to Report
The best career advice ever: Catherine Mayeux's "Just get the facts"
"I was always writing around my lack of information... I didn't have the details, I just had the flare"
Why this became "the most important moment in my career as far as turning it around"
The philosophy that changed everything: "Take the little and make it big"
The Mike Trout example: finding the Make-A-Wish kid photo behind the locker
[45:00-55:00] Stories That Matter: The Tyler Ugolin Story
Calling Victor Ugolin just days after 9/11
Why Victor called back: "What if I just tell you about my son?"
The 40-minute conversation and what changed his mind
Remaining close friends for over 20 years
The supernatural moment: meeting Tyler's high school girlfriend in a random Penn State coffee shop
[55:00-65:00] Books, Regrets, and Rich Gannon
Writing his first book about the 1986 Mets
The Roger Clemens book: "I kind of did it for the money"
Why you need subjects with depth or surrounded by depth
The three-pronged criteria: Will it hold my interest for two years?
The hilarious Rich Gannon "Sexiest Man Alive" mixup with Elvis Grbac
His evolved stance on Hall of Fame voting for steroid users
[65:00-75:00] The Art of Door Knocking
The scariest door knock: JR Rider's house in Arizona
"Bro, you cannot just show up in my house... So what are you working on?"
How showing up with his USFL book turned the situation around
The Nashville apartment with blood and bullet holes
Why good judgment sometimes means ignoring your editor's advice
[75:00-85:00] Writing Advice: The Power of Details
"It's not just a soda... It was a Fanta orange soda with the peel ripped off and some lipstick stain on the rim"
Russell Baker's wisdom: having the villain bend over to smell a rose
"Show the complexity of humanity"
Why details matter more than ever in the age of 22-second video clips
The Bronx Zoo by Sparky Lyle: the book that became his model
[85:00-95:00] The Tupac Book & Hip Hop
Interviewing 650 people for the Tupac biography
The beautiful butterfly kid at Baltimore School for the Arts
"The type of person who would gently remove a ladybug and place it aside"
The contrast: going home every night to a hellscape in East Baltimore
Who shot Tupac? "Orlando Anderson, a hundred percent"
[95:00-105:00] Press Box Chronicles: The Unlikely Hit
Starting TikTok out of spite after a columnist called him an "old relic"
His son's advice: "Don't do TikTok... don't talk politics, don't use filters"
When 3.0 Labs approached him: "Nobody's gonna care. Why would anyone care?"
The 1984 San Diego Padres episode that mysteriously went viral
"My whole career bookwise is nostalgia powered. Sports is all about nostalgia to me"
Planning a tour (even though "nobody's gonna wanna come and see me")
[105:00-115:00] Parenting Philosophy
"The greatest gift of this career: I was available for everything"
Being the "class mom" and never missing a moment for a TV game
Why he hates "hashtag girl dad": "I wasn't a girl dad, I was a dad of a kid who I freaking loved"
His wife Catherine's parenting book "Ignore It" and why attention-seeking behavior should be ignored
The Halloween/World Series example: "That's a horrible mistake"
[115:00-125:00] Catherine's Kidney Donation
The Starbucks flyer that changed everything
"Would it be weird if I donated a kidney to a stranger?"
Meeting Eli and Monica for the first time on the day of donation
How they became their closest friends in California
Why it's one of Jeff's proudest moments (even though it was her accomplishment)
[125:00-135:00] Life & Career Lessons
"Another person's success does not detract from yours"
Letting go of the goal to be "the greatest sports writer who's ever lived"
"My whole career has been just a total lark... I get to write about sports and hip hop for a living"
If you treat people kindly, people remember (and vice versa)
The Tupac book example: getting help from sports media friends he'd known for years
[135:00-145:00] Advice to Young Journalists & Writers
"Don't be a jackass... none of it's that important"
Choose projects that will hold your interest for two years
In the age of fast content, you'll stand out if you actually report
View each chapter as a long feature (credit: John Wertheim)
Why you don't need an editor hanging over you to be productive
[145:00-End] Rapid Fire & Final Thoughts
Playing basketball Saturday and Sunday mornings (the mediocre game continues)
Pearl Washington: his favorite basketball player of all time
The two pieces of memorabilia he keeps: the '86 Mets ball and JR Richard's autograph
What he'd tell his 40-year-old self (or better yet, his 25-year-old self)
Final wisdom: "Just be decent to people... and don't forget about details"
Resources Mentioned:
Books: "The Bad Guys Won," "Showtime," "Boys Will Be Boys," "Football for a Buck," "The Last Folk Hero" (Bo Jackson), "Gunslinger" (Brett Favre), "Three-Ring Circus" (Shaq & Kobe), "Tupac Shakur: The Authorized Biography"
Press Box Chronicles on YouTube
"Ignore It" by Catherine Pearlman
"The Bronx Zoo" by Sparky Lyle and Peter Golenbock
"Conquering the Corporate Career" by Stanley Herz