RICK REILLY’S CAVAN ancestry lost their apostrophe at some point across the Atlantic and down the years, though Rick has rediscovered it and tattooed the Ó’Raghallaigh family crest on his back. 

File photo of Rick Reilly, at the 2012 Super Bowl. Francis Specker Francis Specker

“I love Ireland, it’s my favourite country. I decided that one day in a pub when I asked a guy, ‘What do you think is the national sport here?’ And he said, conversation.” 

Reilly has spent most of his life telling stories through sport, and is this week’s guest on our sportswriting podcast, Behind the Lines. 

(Behind the Lines is exclusively available to members of The42. Each episode features a lengthy interview with a writer about their career and their favourite pieces of sportswriting, so for access to a 57-episode back catalogue, head over to members.the42.ie.) 

Few are more identifiable with the glory days of Sports Illustrated than Rick Reilly: the magazine reserved their most expensive ad-space for alongside his back-page column.

He is an 11-time national sportswriter of the year, has been inducted into the sportscasting hall of fame, three of his columns have been read into the US Congress, and USA Today have called him “the closest thing sportswriting ever had to a rock star.” 

“That’s kind of like being the world’s tallest midget. It was kind of a backhanded compliment.” 

Reilly began by winning a competition to become a sportswriter. It was a Colorado-wide search for the best sportswriting in high school, in which contestants were given 20 facts about a football match and told to write a report. Among the buried facts was the victorious coach’s wife having a baby during the game, and Reilly led with that.

He won, and later found himself working as a bank teller alongside the wife of the competition’s judge. 

He introduced himself as Contestant No.42, and soon had a job alongside said judge at the local paper. He quickly shot to the back of Sports Illustrated, setting himself as separate to the rest with a series of features and, above all, his column, The Life of Reilly. 

He had an expense account and a kind of fame but above all, he had time. (The writers reading should avert their green eyes: they gave him a week to write an 800-word column.)

“My favourite writer is Oscar Wilde. And he said, ‘Never write a sentence you’ve already read.’ That meant you had to go through every piece and take out clichés.

“My paralysing fear was that people would get bored with it. So each week I would try to make it different. So if last week I was mad, this week I’d be funny. And if last week I was funny, this week I’d be heartbreaking  And then I’d be break a story: whatever I could do to make it different.

“And this was before the internet. People had their local paper, they had USA Today and they had Sports Illustrated, so your field of possibilities was so much bigger. Now everybody with an internet connection thinks they’re a sportswriter and everything’s kind of been done.” 

Reilly left Sports Illustrated for ESPN in 2007, as the industry jackknifed online.

He did a lot of TV work for ESPN and continued to write his columns, some of which became buried beneath an internet pile-on, notably a 2013 piece in which he dismissed calls for Washington to drop ‘Redskins’ from their name. 

“They [ESPN] tripled my salary. What am I gonna do? People say, ‘He sold out’. Yeah, they tripled my salary! Sportswriting is not a thing where you ever get your salary tripled.  

“I always wanted to retire at 40 but I couldn’t do that. Then I wanted to retire at 45 but I couldn’t do that. But when I made that move I knew I could retire, and I did at 54.”

The money was pretty much the only thing that was better. 

I know that upsets some people but also, you could see where the cards were laying, right? Sportswriting was becoming, ‘Tweet it, Facebook post it, get it out, smash out another 125 words.’ It was not the thing that I grew up with, which was to make it 800 words, and make it the best 800 words you can possibly do. They gave me a week – a week! – to write 800 words, to write sentences you’d never read and to make the words jump off the page and squirt orange juice in the reader’s eye.

“The salad days of sportswriting were fast leaving, I wanted to try TV and I did, and it wasn’t as much fun as writing, I can tell you that.

“The perfect example is Bill Simmons. My time was coming up to the end at the time I switched to ESPN. And then his time was just starting because he knew how to tweet, and he knew how to post things, and he knew how to get MySpace friends, and he knew how to write mailbags.

“And he really listened to what all these people with all their internet connections were saying back to him. And he did columns where he took photos and then posted them on Instagram, and I was not ready for that. I could write 10 pages and make you cry or laugh and it took me a month. Or I could do 800 words and it would take me a week.

“But he was now and I was not ready for everybody having an opinion on me. At Sports Illustrated, sometimes the letters were the best writing you’d get. ‘Not only was this guy ripping me to shreds, he wrote it better than I wrote the column!’ It took some effort to write a letter to Sports Illustrated.

“Whereas there’s not a lot of effort in tweeting ‘Yeah, your sister’s ugly and I hope you get gout in your ear.’

“I think I was a bit anachronistic.” 

And so Reilly retired to focus on his other writing, including novels and screenplays and, ultimately, last year’s classic work of non-fiction: Commander in Cheat: How Golf Explains Trump. 

Donald Trump plays a round of golf at his Turnberry course in 2018. PA PA

“I had retired and we were living in Italy for three months. I was sitting there drinking my Campari and working on a novel or whatever it was, and I would check my Twitter just to see what crazy crap he had said.

“He was saying stuff like, ‘I’m a champion so vote for me, I’ve won 18 Club Championships against the best players.’

“And I’m like sitting there like, ‘You liar!’ Because he already told me how he won those Club Championships: he would open a new course, play the first round by himself, and he would call that the Club Championship, which is kind of despicable but also really genius. Because unless Melania gets hot, he’s gonna win!” 

The book’s tales of cheating are incredible – Trump once massaged his score in a matchplay with Tiger Woods and has earned the nickname Pele, so often does he kick the ball on to the green – but those of his grift are even more staggering. 

For instance, Trump keeps eight goats on his Bedminster course to get an $80,000 farmland tax break. And on the 14th hole of his Washington course by the Potomac River, there’s a plaque commemorating a Civil War battle that never happened. Also on display is a coat of arms supposedly belonging to the Trump family, which was in fact taken without permission from the family of a former ambassador to Belgium under Harry Truman. It (fittingly) features the Latin for the phrase ‘Never Concede’ and (comically) replaced the Latin for ‘integrity’ with the word ‘Trump.’ 

“Golf is like a pair of bicycle shorts: it reveals a lot about a man. And it really revealed a lot of ugliness about him.

“It really did resonate with people, because you can say what you want about politics, but don’t screw with golf. Golf is a gentleman’s game. I don’t cheat against you and you don’t cheat against me, even though we’re hundreds of yards apart. It’s because it’s built into the very fabric of the game. But this guy’s not like that.” 

Reilly hasn’t since earned Trump’s scorn on Twitter, which Reilly reflects on with what seems a tinge of regret. 

“One of my good golfing buddies is a really good friend of his. My buddy said, ‘Look, don’t get into a Twitter war with this guy. You’ll lose’.

“I probably would have sold about five times as many books if he started tweeting about it. He purposely seemed to stay away from it.” 

To listen to the full interview with Rick, as he talks more about his career and tells stories of competing at the World Sauna Championships and spending time with a wrestling Mexican priest, subscribe at members.the42.ie.