$400 hotels, jet setting and six-course dinners: What working at Sports Illustrated was like 20 year ago

Jeff Pearlman has ascended to become a New York Times bestselling author and one of the most celebrated sports writers in the industry. Although his career began at Sports Illustrated, his talent for uncovering and sharing deeply personal sports narratives has transcended time.

Though the magazine’s influence has waned, Pearlman remains a leading voice in the field and has embarked on a new chapter, sharing candid stories from his career on TikTok. And Pearlman’s latest iteration revealed what working at SI was like two decades ago.

@jeffpearlmanauthor

Here’s what it was like to be a Sports Illustrated writer during print’s glory years. (In a word: Awesome!) #sportsillustrated #writersoftiktok #journalism #tomverducci #rickreilly #steverushin #magazines

♬ original sound – Jeff Pearlman

“From 1996 to about 2003, I worked for Sports Illustrated,” Pearlman began, “and working for Sports Illustrated back then was the best job in media. First of all, it was my dream job, and when I got hired, I called my mom and I was crying because I actually told my mom when I was in high school that one day, I was going to work for SI. So, it was a dream come true… and when you’re a baseball writer for Sports Illustrated, which I became, if you’re single and you’re in your 20s, it’s ridiculous.

“The rule was you could stay in any hotel, as long as it was under maybe $400 a night, which was a lot of money back then and still kind of a lot. No. 2, Spring Training, just as an example; you’d rent a car, go to Florida, and just go from training hub to training hub to training hub. You’d go from team to team to team. You might have the Phillies one day and the Pirates another day. And you’re driving around, and I always rented a convertible, and they never minded.

“So, I’d be driving around Florida in February while my friends are freezing their a**es off in New York. And you would just go around, and let’s say you wanted to do a piece about — I don’t know — Scott Rolen? You’d go to Phillies camp, and you’d call the team. They would love that Sports Illustrated wanted to do a piece. Scott Rolen would generally love that SI was going to do a piece. They’d be like, ‘You want to get breakfast with him?’ ‘Yeah, sure.’ You go to a cafe with Scott Rolen and have breakfast and talk about life as a baseball player.

“Sports Illustrated was royalty, and if you worked there — it’s not like I did anything to earn this, I worked hard — but you were royalty in a sense. And once the season started, I used to do this thing called the ‘Inside Baseball’ column, and really myself and another guy, Steve Cannella, we did it together. We would go two, three places a week. So, it might be like, ‘Alright, go to Chicago on Monday and talk to Kerry Wood. And on Wednesday, we need you in LA to talk to Shawn Green. Then, you know what? On Friday, since you’re going to be on the West Coast, go up to San Francisco and do something on Jeff Kent.'”

Pearlman painted a picture of unparalleled access, lavish perks and the intoxicating thrill of being a young journalist at the top of the industry.

“And you would fly to all these places, and you would stay in really cool hotels,” Pearlman continued. “And you would show up, and it’s like, ‘Ooh, Sports Illustrated’s in town.’ Like, it meant something. And then, you’d write something, and it would appear in your favorite freakin’ magazine; three million people would read it. And it was enormous, and you just felt like the f*cking, motherf*cking man. You just did. It was such a thrill to write for SI.

“I gotta say, SI was rolling in money — rolling in money. You had to work late on Sundays if you were in the office. This is like when you’re a fact checker, reporter, or editor, and they would cater like a six-course meal. They had town cars that took everyone home at night. So when you were down at night on a Sunday, you would get a ticket — it was all paid for — and there would be a town car waiting for you downstairs outside the Time Warner building to take you where you need to go. It was so insane.

One year. Before I got there, they wanted to celebrate winning a national magazine award. So they sent the entire staff to the I think it was to the Atlanta Olympics just to enjoy three days of the Olympics. Go to any sports. You want anything it’s all paid for. It’s bonkers, how much money they had, how successful it was, how great you felt working for Sports Illustrated.”

“People loved Sports Illustrated – they just did; it meant the world. And I was just there at the last great era of print…and you were a king. I was young and cocky and loved it and gobbled it up, and I’ve never forgotten the joy.”

[Jeff Pearlman]