Sports Illustrated’s Jon Wertheim goes for the unlikely angle over the power winner

Jon Wertheim is Sports Illustrated's executive editor and is confident that the future is more promising than ever.

When Jon Wertheim was in high school, he once told his mother that she didn’t understand him. Writing was the thing in life that gave him the most pleasure. His mother, Judy Wertheim, remembers the beautifully crafted letters he sent home from summer camp when he was 10 years old. She remembers when he submitted an essay entitled “Abraham Lincoln and The Treason Trial” to the Abraham Lincoln Statewide Essay Contest. He won the contest that year. And the next.

(Photo courtesy of Jon Wertheim)
(Photo courtesy of Jon Wertheim)

Wertheim is now the executive editor of Sports Illustrated, a historic magazine that is, like all magazines, fighting for its life. Many of Wertheim’s colleagues warn that as the digital revolution upends traditional journalism, writers should run in the opposite direction. Wertheim disagrees. Today is a Tuesday, and Wertheim has already worked on his new book and taped a video segment for the Tennis Channel. Now, he is sitting down to write his Wednesday tennis column for the Sports Illustrated website. This kind of variety is new. And, he says, it’s exhilarating.

Now 44 years old, Wertheim ascended from fact-checker to one of the most powerful forces behind Sports Illustrated in less than 20 years. But he doesn’t see his journey as exceptional. He sees a boy who followed Indiana basketball religiously, a teenager who wrote for his high school newspaper because it meant he could do “cool stuff,” and a man who stumbled into a job that paid him to do both.

Wertheim grew up in a small, suburban neighborhood outside of Bloomington, Ind., or “The Great Midwest,” as he calls it. When he moved to the Bay Area briefly in sixth grade, he remembers being awestruck by its diversity. In Bloomington, Ind., there were times when there were no African-Americans, no non-whites in any of his classes. Indiana had countless virtues; diversity just wasn’t real high on the list.

One of those virtues was a statewide love for sports. His mother and father didn’t always know what team Michael Jordan played for, but you could bet that everyone else in Indiana did.

In this college town in the Midwest, knowing about sports was social currency.

“In Indiana, you kind of had to be into sports to have any kind of social relevance,” Wertheim said. “In this college town in the Midwest, knowing about sports was social currency.”

In 5th grade, Wertheim ordered his first Sports Illustrated magazine to be delivered to his doorstep. With each flip of the page, he thought of the endless possibilities that sportswriting promised.

“There was a guy, Curry Kirkpatrick, who would write about tennis one week and basketball the next,” Wertheim said. “And I was like, he’s playing horseshoes with George Bush in Maine one week and the next week he’s at Wimbledon. That’s gotta be the coolest job in the world.”

But at 22 years old, sportswriting didn’t seem like the reasonable next step for Wertheim. After taking a gap year to write for the Portland Trail Blazers’ fan magazine, Wertheim moved to Philadelphia to attend the University of Pennsylvania Law School.

“Honestly, going to law school was kind of a path of least resistance kind of thing,” Wertheim said. “It seemed like a logical thing to do, you know? I wasn’t hellbent on being a lawyer, but that’s what people did.”

Wertheim quickly realized that law was not for him.

“I worked at a law firm the summer after my first year. And I was like,‘Yeah, there’s no way I’m doing this for two more years.’”

The next summer, Sports Illustrated happened to be looking for a writer with a legal background. Wertheim enjoyed his work at the sports magazine so much that he stayed on beyond the summer and throughout his third year of law school. The week after graduating in 1997, he began writing about the world’s greatest athletes for a living.

When Wertheim was growing up, two of his sports heroes were Reggie Miller and Steve Alford. Alford played for Indiana University and Miller played for the Indiana Pacers, so Wertheim was surrounded in droves by fellow fans. But not everyone shared his admiration for tennis stars Yannick Noah and Martina Navratilova. Wertheim, who picked up a racket for the first time at 10 and later played tennis for his high school, had a deep appreciation for their unique styles. Their games were risky and different; they liked to go for the angle over the power winner.

Today, Wertheim’s passion for tennis remains. Though he covers a broad range of topics, tennis is the guilty pleasure he can’t seem to quit. For one, he is in awe of the mixed gender cast that tennis represents.

“You get people from different backgrounds, different sensibilities, different ages and genders,” Wertheim said. “Serena Williams was born within a few weeks of Roger Federer, and outside of that, I think they could not be more different. I think that speaks to the sport. Tennis really has this capacity to accommodate a broad range of people.”

Since 2012, Wertheim has been a Tennis Channel commentator for the four grand slams and Indian Wells. He also still likes to get on the court himself occasionally. His wife, Ellie Wertheim, knows better than anyone that Wertheim doesn’t let any ball slip past him.

“Jon can get back every single ball,” Ellie Wertheim said. “It’s frustrating to play against him, because there’s no ball he can’t return.”

Wertheim exercises regularly, and at 5-foot-10 and 160 pounds, he could harness his power to hit lethal groundstrokes.

But just like his tennis heroes, Wertheim values nuance over power on the court. In the newsroom, he has the same mindset. He would much rather find the unlikely angle than go for the obvious shot.

If no one was interested in sports, if no one was interested in storytelling, if no one was interested in news, then I would be worried … But I feel like people are more interested than ever.

Stephen Cannella, now assistant managing editor at Sports Illustrated, joined the magazine the year before Wertheim. From the start, Cannella admired Wertheim’s ability to find the most compelling stories in the least likely places.

In 2005, Wertheim escorted Sports Illustrated readers away from tennis stadiums and basketball arenas and into shadowy pool halls. Wertheim wrote about a depressed, overweight 15-year-old named Danny Basavich, who found salvation at Elite Billiards, a 25-table hall with a musty smell and eclectic cast of characters. By 17, he had become “Kid Delicious,” an indomitable pool hustler.

“We all write, edit and read a lot of stories about mainstream athletes,” Cannella said. “But this was just such a unique story. It was a window into this pool hustler subculture. Jon is a Midwestern guy; he went to law school. But he has this way of making any subject comfortable, this ability to navigate any world.”

Immediately, Wertheim’s story, “The Amazing Adventures of Kid Delicious and Bristol Bob,” draws the reader to the window of that subculture. In the converted ballroom of a nondescript hotel, the reader sees Danny Basavich suspended over the pool table and hears the clinking of beer bottles. Then, the reader follows Basavich around the country as he sinks ball after ball into pocket after pocket.

Jack McCallum, a former Sports Illustrated staff writer who co-authored “Foul Lines: A Pro Basketball Novel” with Wertheim, attributes the sharpness of detail in Wertheim’s stories to his searing intellect. McCallum, who is 20 years older than Wertheim, mentored him when he first arrived at Sports Illustrated. He knew early on that Wertheim could run the magazine some day.

“When we were writing the book together, we sort of reversed age roles. I would be more the impulsive one, the guy to think of 10 ways to write it and none of them would be right,” McCallum said. “Jon’s lawyer mind would make him want to study it a bit more.”

Today, Wertheim runs the magazine. As executive editor, he thinks about much more than his next column or appearance on the Tennis Channel. He thinks about the future of Sports Illustrated. But he’s confident that the future is more promising than ever.

“If no one was interested in sports, if no one was interested in storytelling, if no one was interested in news, then I would be worried,” Wertheim said. “But I feel like people are more interested than ever.”

(Homepage photo courtesy of Jon Wertheim.)

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