THE LIFE OF REILLY
Former celebrity writer at Sports Illustrated set his sights on Trump with Commander in Cheat
Rick Reilly was between bites of a samosa during a dinner a couple of months ago in Washington, pondering his career. He was an 11time national sportswriter of the year during his heyday at Sports Illustrated, a celebrated longform writer and ultimately the country’s most influential, and highest-paid, columnist during a career that spanned three decades.
And then?
“I hit the wall, man,” Reilly said. The downslope of Reilly’s career after he left SI for ESPN in 2008 was both sudden and jarring. He was caught recycling old material; his father-in-law, a Native American, accused Reilly of misquoting him in a column defending the Redskins’ team name; the puckish humour that once defined his writing lost its edge. In describing his excitement if he were to win a golf major he wrote, “I’d go absolutely electroshock, three-alarm, bat-guano nuts!” in 2009 — and again in 2014.
Reilly’s career arc remains somewhat hard to comprehend: He went from the pinnacle of the profession to the punchline of internet headlines:
“What happened to Rick Reilly?” “Rick Reilly repeated the most predictable bad joke ever”
“The Death of Reilly: Why the ESPN columnist couldn’t survive in the era of Bill Simmons and Nate Silver.”
Reilly released Commander in Cheat a few months ago, an expose on President Donald Trump’s alleged rampant golf cheating. The book hit the bestseller list and thrust Reilly, 61, back into the media spotlight. He did a slew of cable news hits and was excerpted by Politico. He recently tweeted: “As Trump continues to spend $100M+ of our taxes playing golf, I’m told the course condition at Trump Bedminster sucks these days cuz he had to fire so many illegal groundskeepers. Imagine that.”
“These political guys can’t get enough,” he said. “I got reviewed by The New Yorker!”
Reilly’s old sports buddies, he said, have been less interested.
“Maybe it’s too political,” he offered. “A lot of them don’t want to touch it.”
During a talk at a book signing Reilly said: “Golf is the best game.”
His reedy voice cracked and it rose and his eyes welled as he talked about Trump.
“Somebody’s gotta call him on these lies!”
Reilly choked back tears, as he explained that his father taught him to play the game.
“If a sportswriter can stand up to Trump, why can’t a Republican senator?” he asked.
Reilly’s book is filled with vivid allegations about Trump’s cheating — how he once threw broadcaster Mike Tirico’s ball off the green during a round, how he manipulates the value of his courses to get tax breaks, how he exaggerates his golf scores.
It is also filled with Reilly’s patented shtick.
“Golf is like bike shorts,” he writes. “It reveals a lot about a man.”
If the book is Reilly’s chance to consider Trump through golf, it is also an opportunity to consider Reilly, a man without a home in the industry he once ruled from his perch on the back page of Sports Illustrated. If Reilly felt the sports press was only tepidly interested in Commander in Cheat, so, too, is it only tepidly interested in Reilly these days. The feeling is mutual.
“The truth is I wanted to retire when I was 45, but I didn’t have enough money,” Reilly said. “I wanted to retire at 50, but I didn’t have enough money.”
Reilly continued: “People called me a sellout when I went to ESPN, but I tripled my salary. Who wouldn’t sell out for that? I got kids!”
Reilly grew up in Colorado a devoted reader of Sports Illustrated, looking up to Dan Jenkins, the irascible Texan who inspired a generation of sportswriters from Mike Lupica to Tony Kornheiser. By 27, he was hired by the fabled magazine and was an immediate star.
“He could make you laugh and cry in the same story,” said former SI colleague Rick Telander. “He was pure writing talent.”
In a single issue in the spring of 1986, Reilly announced his arrival with a penetrating profile of famed Los Angeles Times columnist Jim Murray — another personal hero — and a piece from Augusta on Jack Nicklaus’ Masters win.
Reilly wrote poignant longform pieces about Bryant Gumbel’s tortured relationship with his parents, and a scathing rebuke of hazing at The Citadel.
His favourite was a story on former Cincinnati Reds owner Marge Schott.
“Alone in her bedroom, alone in a 40-room mansion, alone on a 70acre estate, Marge Schott finishes off a vodka-and-water (no lime, no lemon), stubs out another Carlton 120, takes to her two aching knees and prays to the Men,” read the lede.
“Everything on that story went my way,” he said, his eyes lighting up. “We said we needed to shoot the story and she says, ‘Oh I pray to my husband, father and fatherin-law on my knees every night.’ I said, ‘Could we shoot it?’ and she says, ‘OK.’ We’re all set for the shot, ‘Come on out of the bathroom, Mrs. Schott’ and she comes out in a lime green teddy!”
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.
By 1998, Reilly had mostly given up the longer stories to write the back-page “Life of Reilly” column at SI, where his humour was still on display every week.
He was so good that college kids plastered their bathroom stalls with his copy, and so big that he starred in a Miller Lite commercial with model Rebecca Romijn.
When Reilly was poached by ESPN in 2008, it was a tectonic shift in sports media. Reilly reportedly got paid more than $3 million a year, a fortune for a sportswriter. (Asked to confirm the number, Reilly laughed and said, “You think I’m going to say that on the record?”)
But the move came just as an ascendant Bill Simmons was on his way to becoming the industry’s most influential voice with his first-person ESPN.com columns from a fan’s perspective. Deadspin also emerged as a new generation’s voice of media criticism.
Reilly wasn’t quite the same, either, and the reported salary, fairly or not, put a target on his back. Deadspin chronicled his every misstep, including catching him repeating passages from old work time and time again. Reilly wrote columns that were just listicles of lame golf jokes and he tweeted at fellow media members about how hot his wife was. In 2014, ESPN dropped Reilly’s column. (He continued to do some TV work before officially retiring.)
Reilly flashed his brilliance at ESPN, including his debut column about his alcoholic father, but the slip-ups contributed to a feeling that his heart wasn’t in the work. Plenty of sportswriters make the jump from distinguished print careers into TV, but few felt like such diminished versions of themselves.
“At his best, his work seemed original and incisive and fresh, both in terms of the concepts and execution.
By the end of his tenure at ESPN, that freshness wasn’t there anymore,” said Josh Levin, Slate’s national editor, who once chronicled Reilly’s overreliance on tooth jokes.
“The opportunity when he left SI felt like a really big opportunity, and then the work he produced didn’t meet those expectations.”
A former colleague of Reilly’s recalled seeing him at a sporting event a few years after he left for ESPN.
“He’s sitting by himself in the back row of the press box, not talking to anyone and no one’s talking to him,” the former colleague said.
“He used to be the life of every event he covered and it was just stunning to see that this was who he was now.” To hear Reilly tell it, the joke is on everybody else. He lives in Hermosa Beach and spends part of the year with his wife, Cynthia, in Florence. He paddleboards. He plays piano. He meditates. He has a mantra: “I don’t steer the river.”
If there was a perception that Reilly was mailing it in at ESPN, Reilly suggested he had simply run out of things to say.
“The first 30 times you go to the Masters is great, but then what?” he said. “You can only do ‘Set against the Magnolias’ so many times. These guys like (Boston Globe columnist) Bob Ryan that are still grinding it out, I don’t know how they keep doing it. I think they must like sports more than I ever did.”
Today, Reilly says, his world has opened.
“Sports is like this one tiny corner of life. Don’t you want to travel the world?” he asked. “Don’t you want to see the Taj Mahal?” (Has Reilly been to the Taj Mahal? “No, but that’s next!”)
In retirement, Reilly has fed tigers and he rode an elephant in Thailand.
He works on screenplays a few hours every day (he co-wrote the 2008 film Leatherheads). In his view, much of the consternation over his career can be dismissed as internet chatter.
“Mark Cuban once said to me, ‘Do you ever open your door so someone can come hit you in the face with a baseball bat?’” he said. “‘So why would you read your Twitter mentions?’”
The flap with his father-in-law was a simple misunderstanding and they remain close, he said, while recycling his material was an honest mistake.
“You’d have to turn in a column every week — vacation, travelling, it didn’t matter, every single week,” he said. “I had this list of rainy day ideas. I’d find them on my computer and there were times when I hadn’t pulled one from the ‘possible’ file to the ‘already written’ file.”
Some of the criticism, though, seems to cut a little deeper.
“There is this perception that Simmons forced me out of the business,” Reilly said. “I like Bill, I think he’s a genius, my kids read him. But one day he writes 8,000 words about (former NBA star) Kevin Garnett and I ask them about it and they said, ‘We skimmed it.’ I asked Simmons about it, and he said, ‘Oh yeah, I know they’re not reading every word.’ I never wanted to be skimmed.”
Of Deadspin, Reilly said, “Is that what you told your mom you wanted to be? A sportswriter who criticizes other sportswriters because they got the job you wanted? I think that’s sad.”
Somebody’s gotta call him on these lies! If a sportswriter can stand up to Trump, why can’t a Republican senator?