Keystrokes of Genius: Jon Wertheim awarded Eugene L. Scott Award at International Tennis Hall of Fame's Legends Ball

WATCH: Jon Wertheim's acceptance speech at the 2022 Legends Ball

NEW YORK—He’s turned phrases for Sports Illustrated since the mid-‘90s, and written page-turners on topics ranging from billiards to economics to mixed martial arts. He’s finishing his fifth season on television for 60 Minutes, and he just wrapped a series of 120-minute US Open preview shows on Tennis Channel.

But to many, Jon Wertheim isn’t best known for any of these prominent journalism roles. Instead, it’s his weekly forum with you and I, rather than exclusive interviews with Venus Williams, Jerry Seinfeld or Kobe Bryant, for his popular tennis mailbag on SI.com.

“It’s been a real source of pleasure,” says Wertheim, once again answering questions from a longtime reader. “I see a lot of parallels to podcasting—it’s kind of informal, but it can be journalistic. Hopefully you’re tapping into what people are talking about.”

Those people include, as Wertheim puts it, a “core group of readers, randos and celebrities” whose connections to tennis vary greatly. But whether they want to talk about forehands and backhands, or fashion and cultural representation, the conversation has continued for nearly 25 years. It’s “a labor of love,” says Wertheim, and a way for him to keep up with a sport that seemingly never stops moving.

That’s essential for a busy father of two, whose workload demanded a smartphone long before they were ubiquitous, plus the requisite smarts. After graduating from Yale in 1993, Wertheim went on to pursue law at Penn. But he soon discovered that the essence of an $9/hour summer job in New Haven surpassed the more lucrative but sometimes soul-crushing work of a summer associate at a law firm.

“I was charge of the locker room—I later got promoted to ballkid supervisor,” Wertheim says with a laugh about the old Connecticut tour stop. “I was 19, 20 years old, and it was a real glimpse behind the curtain. You begin to realize all the dimensions to the sport, and all the things you don’t see when you watch it on TV.”

When Wertheim made his way to SI, after a successful internship, he was told that while he would be writing features on a variety of subjects, he needed to pick one sport to sink his teeth into. Though proudly born in the college basketball mecca of Bloomington, Ind.—Hoosier country—the choice was clear: tennis.

“You can be the Lakers beat writer and not talk to LeBron James,” says Wertheim. “And what you realize in tennis is that it gets very small, very fast.”

Wertheim has made the most of his access, cultivating relationships with players and within the industry that has made him an engaging, sharp and often brilliantly humorous authority on the game. And for his “commitment to communicating honestly and critically about the sport, and who has a significant impact on tennis,” Wertheim was awarded the Eugene L. Scott Award on Saturday night in Manhattan at the 2022 Legends Ball, an annual benefit for the International Tennis Hall of Fame. The honor is given in memory of the late Hall of Famer Scott, who was the publisher of Tennis Week magazine.

Roughly three decades after that seminal gig as an undergrad, Wertheim remains fascinated by tennis. He’s traveled to Mallorca to chat with Rafael Nadal for 60 Minutes; he annually solicits advice from diehards for an annual do’s-and-don’ts primer on the US Open; he writes short-form and longform with equal facility; and he’s must-follow on Twitter—his micro-prose a combination of Wojnarowski-like newsbreaking, and wit fit for Gens X through Z.

At the heart of Wertheim’s talents is not only a wordsmith’s command of the language and wide-ranging expertise, but also an innate ability to get renowned stars to open up and tell us something we haven’t already heard. He puts them at ease with a style that other writers, including this one, look up to.

“One thing I’ve noticed through the years is that athletes, celebrities, musicians, high-level academics—they’re used to getting their ass kissed so much that a little bit of pushback, of resistance, of a critical eye—they respect and like a certain challenge,” theorizes Wertheim. “They like a real conversation where it’s not, Everything’s amazing, and you’re incredible.

“It’s a fine line, you don’t want to be confrontational. But you see it in tennis. You can ask Novak Djokovic a tough question. I’m not here to get your autograph; I’m not here to get a selfie; I don’t need you to post this on your Instagram—we’re going to have an adult conversation. It’s much better received.”

When you read the investigative pieces Wertheim spends countless hours on—across a spectrum of storytelling that has touched on important social issues; the apex of the Federer-Nadal rivalry; a profile of prolific entertainer Viola Davis; even a feature on the Alaskan island of Attu (site of the only land battle in the United States during World War II)—you see how his approach pays off.

And then, when you read his mailbag and realize that Jon puts the same care into his discourse with an average Joe as he does with an international pro, you see why the choice for this year’s Eugene L. Scott Award was clear.

“I think it really speaks well to tennis that different styles and different sensibilities can be accommodated,” says Wertheim, staying true to his modest, Midwestern roots.

Variety is undoubtedly good, but if everyone could choose to write like Jon Wertheim, most surely would.