Life of Reilly: The rise, fall and rise again

The incident in Pittsburgh was a sad attempt to stay relevant in a way he knew others would recognize.
Lawrence O'Donnell paid him the highest compliment a writer can get when he had him on a few weeks ago.
To the effect of: You made me interested in a subject - golf - that I couldn't have given the slightest shit about.
So that takes some doing. But it took 15-20 years of beclowning himself to get there.

 

I'm sure he would, too.

 

But if there can be a certain romanticism over sports writing — and over the most successful sportswriters — Reilly said there was also a toll.

“Every one of those stories took a year off your life,” he said. “They’d give you five, six weeks for a story but it better be the best damn story you ever wrote. Gary Smith [another SI writer] and I used to talk about it. You’d be up all night, you’d hear the characters in your head, you couldn’t talk to your family.”

The deadline pressure could be so intense that his nerves gave Reilly severe stomach pains, putting him in the hospital twice. “I had to go to therapy before I learned I could breathe through the panic attacks and realize that I was good enough to be at the magazine,” he said.


To me, this is one of the most honest things ever written about longform feature writing. Kudos to anyone who could do it and treat it just like a job. I've been there on the stomach stuff (not in the hospital, but unable to sleep because of pain caused by a story), and it's misery.

Reilly won by every metic. Debates about "legacy" are generally dumb. He understood the darkness of subjects in ways that very few feature writers did, but that almost wrecked him, and so he wrote a great column for nearly a decade and then he ran out of stuff to say. It's ok. It happens. Simmons ran out of stuff to say as well, but he was able to pivot to podcasts. That saved him from a similar fate. Anyone who says "Just shut up and go back to doing what you were good at, writing stories" has probably never written several hundred of those stories.

 

Two of my favorite Reilly stories were the travel story that accompanied the swimsuit issue. They were in Cuba, I think, and Reilly had a bit of Hemingway in describing a scooter. “It was a great scooter, Christ it was a great scooter. The horn worked fine.”

I butchered that, but you get the gist.

The other was his story from the Pebble Beach Pro-Am when he played with Kirk Triplett. Well, they hacked it around the track, and at the end Reilly said he’d need 10 shots the next year. “And Trip needs three.”

 

I always think of the Citadel piece. Great work.

Certain personality types don't mesh with me, and I wouldn't want to spend 10 seconds in conversation with him-- but that's just me.

I think the piece portrayed him perfectly... the one thing that I didn't know-- the part that really hit me-- was the pressure. I think every time he had to put out a longform piece, his potential for further greatness was eroded.

Keith Olbermann wrote something similar. The pressure of writing SportsCenter and needing to make it funny and great everyday?-- Eventually drove what was already a predisposition for some mental stuff into full-on cray. They both sabotaged themselves to a certain extent.

 

People who have "big" jobs always come off like assholes when they talk about how hard they are—it sounds like big-timing or something, and a small-town desker pushing out 15 pages a night doesn't want to hear about how writing six stories a year is a lot of work. But it really is hard: It's a different kind of pressure, and it's a different kind of hard, but it's hard. The gloomy rise of the Internet, both because of its pace and its immediate and ungenerous feedback loops, only made it harder. It's an absolutely sapping business, and if you have any weakness at all in you, sooner or later the work will find it and fuck you up.

 

By far my favorite SI writer of that era is Steve Rushin. He was also at his peak creatively-- his stuff was sexy brilliance every week-- when he checked out.

Some of you will tell me that Steve's been busy with this, that and the other... but whatever he's been doing isn't as high-profile. And I'm wondering if the Internet and the pressure got to him as well?

 

It always makes me laugh that one of the first examples of ESPN's extreme leftist agenda is always that they had a Sportscenter hosted by two black anchors.

2019 is a strange fucking place.

 

I've known reporters (female) who have said longform is like a pregnancy - but at least with the pregancy the pain of the pushing comes only at the end of the ninth month.

 

Red Smith pumped out columns 5 or 6 days a week for decades. Cry me a river.

 

He was a god at SI.

One can attain a high level of competence in many things, given enough time and reps. Whenever I read him, I always knew I could never write as well as he did. Not in another life. Not with a brain transplant. Just not happening. No jealousy, just reverence.

It was weird for me when he was hired at ESPN because they pretty much openly crapped on him whenever he would speak ill of Saint Jordan. They even clowned him when he broke the story of Jordan's comeback with Washington.

It may be that the vitriol and ridicule directed at him in the ESPN-and-beyond years is because he was held in such high regard and so many cared deeply about his writing. It's like being a Metallica fan from 1983 and then hearing Load, ReLoad, St. Anger and Lulu. It's more than a downturn in quality; it feels like a betrayal.