Rick Reilly was between bites during a recent dinner in Washington, pondering his career. He was an 11-time 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 Sports Illustrated for ESPN in 2008 was 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; and the puckish humor 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.”

In April, Reilly released “Commander in Cheat,” an expose on President Donald Trump’s alleged rampant golf cheating. The book hit the best-sellers list and thrust Reilly, 61, back into the media spotlight. He did a slew of cable news hits and was excerpted by Politico.

“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 said. “A lot of them don’t want to touch it.”

An hour before dinner, Reilly gave a talk at Solid State Books in Washington.

“Golf is the best game,” Reilly said.

His reedy voice cracked and it rose, and his eyes welled as he talked about Trump. “Somebody’s gotta call him on these lies!” he exclaimed.

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 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. ...

“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!”

He shrugged and took another bite of dinner.


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, Reilly was hired by the fabled magazine and was an immediate star.

“He could make you laugh and cry in the same story,” former Sports Illustrated colleague Rick Telander said. “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 pieces about Bryant Gumbel’s tortured relationship with his parents, and a scathing rebuke of hazing at The Citadel. His favorite was a story on the former Cincinnati Reds owner Marge Schott.

“Alone in her bedroom, alone in a 40-room mansion, alone on a 70-acre 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 father-in-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 Sports Illustrated 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 Sports Illustrated, where his humor 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 again and 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 Sports Illustrated 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. On the night of his book event, he was California tan and looked lithe in his tailored gray suit and a monogrammed white shirt. He lives in Hermosa Beach and spends part of the year with his wife, Cynthia, in Florence. He paddle boards. 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 said, 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, traveling, 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 (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.”


When Dan Jenkins passed away in March, there was an outpouring of tributes to one of Reilly’s role models, a beloved titan of the industry.

In his heyday, Reilly was every bit the golf writer that Jenkins was, and in some ways he loomed over the profession like Jenkins once did. But around sports media circles today, it is hard to find much reverence for Reilly, or a cadre of his acolytes. To a certain generation, he’s as well known for bad Kate Upton jokes as anything else.

“The business has moved away from rewarding people for the work Rick was doing early in his career, the more ambitious stuff. And also, you’ve got to remember it’s hard,” said Washington Post columnist Sally Jenkins, a former Sports Illustrated colleague of Reilly’s and Dan Jenkins’ daughter. “My dad was at his typewriter until the day he died. I think the worst thing you can accuse Rick of is never meeting a joke he didn’t like.”

Added Sports Illustrated Executive Editor Jon Wertheim: “Making people laugh is kind of contagious and there is something seductive about telling feel-good stories and hearing people tell you that they saw you on TV. I still think Rick’s on the Sports Illustrated Mount Rushmore.”

Reilly said he isn’t much concerned about his own legacy. But if there is something he’d like to be remembered for, he said, it’s for standing up for the little guy – which is why his Trump book is a genuine throwback to his old muckraking days.

“I wanted to write columns that made small people feel big and big people feel small,” Reilly said. “Trump’s a bully, and I think it could really change the way people vote. My dad was a lifelong Republican, but I don’t know if he’d vote for this guy knowing how he cheats at golf.”

Reilly likes to say he didn’t want to write the Trump book, that he was jerked out of retirement and compelled to do it. But he’s also looking forward to getting back to the beach.

“(Former ESPN executive) John Wildhack quit ESPN to go be the athletic director at Syracuse or something like that a few years,” Reilly said. “So I called him and I said, ‘Hey that’s great.’ He said, ‘Really? I just want to do what you’re doing. Doing whatever the hell you want. Doing the crossword whenever you want.’ ”

Reilly continued, “Here I thought he had the best job in the world. And he’s just trying to get to where I am.”


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