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'You don't have to be an asshole to be ambitious' - How to land your dream job...via the NBA draft

Jeff Pearlman was this week’s guest on Behind the Lines.

IN MID-90s AMERICA, if a basketball player wanted to be at the Chicago Bulls then a sportswriter wanted to be at Sports Illustrated. 

For Jordan, Pippen, and Rodman, read Rick Reilly, Gary Smith, and Tom Verducci. Jeff Pearlman dreamed of the latter roster…and he joined it at the NBA draft. 

Jeff was this week’s guest on our sportswriting podcast Behind the Lines, which is exclusive to The42 members.

Each episode features a lengthy chat with a writer about their career and their favourite pieces of writing, and the entire back catalogue is available by signing up at 

pearlman_overlay Jeff Pearlman. Source: Jeff Pearlman

In 1995, Pearlman was a brash young reporter who had some of his edges smoothed by an apprenticeship at The Tennessean newspaper in Nashville. Not all of those edges, mind: ambition and creativity endured. 

“For all the bad qualities I had, ambition was a good one. 

“I wanted it really, really bad. I wanted to be a writer at Sports Illustrated. When I was in high school, I guaranteed my Mom I would write for Sports Illustrated. It wasn’t that different to guaranteeing my Mom I would wind up on Broadway. 

“But you don’t have to be an asshole to be ambitious. You can be a empathetic and be ambitious; you can be open to taking advice and be ambitious. 

In 1995 I wrote a letter to Sports Illustrated. I designed the letter to look like it was from the inside of the magazine, I laid it out in a certain way. The magazine would have a ‘Letter from the Editor’ which would sometimes be about one of the staff writers. I created this Letter from the Editor dated 2020, and it was like, ‘Back in 1995, when we first received a letter from Jeff Pearlman we thought, ‘Why would anyone hire this punk nobody?’, but…’ blah, blah, blah. 

“I sent it to Sports Illustrated and I got a call back and they invited me to pitch some stories. I pitched a bunch of boring ideas: ‘There’s a swimmer in Nashville who’s really good; there’s a basketball coach in Nashville who’s really good…’ and they said no, no. 

“Then I pitched an idea. When I was in college at the University of Delaware, I applied early for the NBA draft as a junior, even though I never played college basketball. I just thought I’d see what would happen if I applied to the NBA draft. 

“So I wrote a letter to the NBA, declaring that I wanted to enter the 1993 draft. I didn’t think anything about it until one day my room-mate says, ‘Pearl, there’s a letter from the NBA for you.’  I open it. ‘As of this date, you’re officially entered into the NBA draft.’ 

“A few days later I get a call from the head of security at the NBA, saying, we don’t know who the hell you are. I said, ‘I’m a basketball player at Delaware…’

“Sports Illustrated told me to write that, and that ended up becoming my first column in Sports Illustrated. A few weeks later they hired me as a reporter. 

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“It was the ’93 draft. I was interning at the The Tennessean at the time, and I turned on the draft. I knew I wouldn’t get picked, but obviously there’s this 1% thing in your head thinking, ‘maybe some team will screw up…’ 

“Then in the second round, I think the 53rd pick, the Indiana Pacers announced: ‘Centre, University of Delaware, Spencer Dunkley. It’s the only time the University of Delaware was read out, so I’m sure there was half a second when I thought, ‘Woah, what!?’ but it wasn’t to be.  I’m picturing my own sneaker brand, I’m picturing the greatest 6′ 2″ Jewish forward in the history of the NBA, all kinds of amazing dreams. 

“But I’m still available as a free agent.” 

Listen to the full interview with Jeff on Behind The Lines. To gain access to the podcast feed – and plenty more besides – subscribe at

Highlights from the series’ first 12 episodes are available for free at this link.

Read Jeff’s piece in question here. 

About the author:

Gavin Cooney

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