“I’m so sorry.” It’s the first thing Jason Gay says to me, apologizing for being late. His relaxed smile and kind eyes behind his Warby Parker glasses permeate through the camera of our Zoom call. “I have all the time you need,” he graciously adds. His children are out of the house and the frenzy of March Madness is briefly subdued, giving The Wall Street Journal sports columnist a rare hour of uninterrupted quiet on this Sunday afternoon.
Behind him, a Wilson T2000 tennis racket, the same model of the pure aluminum racket that Jimmy Connors used when he won the 1983 US Open, glimmers on the wall above Gay’s desk. “It’s like winning with a spatula!” says Gay, who grew-up playing tennis. The racket is a token of his love for tennis, a love that comes from his father, a high school tennis coach for more than 40 years.
Every workday, Gay, 53, wakes up at 4 a.m., in the pitch black of his brownstone, before the sun casts light on the Brooklyn Bridge and the bustle of the New York City traffic jump starts the day. Fueled by his daily injection of caffeine, he tip-toes over to his computer, savoring the (mostly) dormant internet and his (mostly) asleep son, daughter, and wife, Bessie.
Sometimes he’ll sit in the dark reading a New York Post article about Pete Davidson or watching a video of Mark Wahlberg working out. But other times, when his morning coffee gives him a rush of creativity, he gets to “work.” If you can call it “work,” he jokes. As a sports journalist, he gets to cover the World Series, plan his trip to Paris for the upcoming Olympics, and most importantly, “spread some lighthearted humor and happiness.”
His readers fervently await his next story to grace the columns of The Journal’s sports section. Gay’s entertaining writing, sprinkled with wry humor, keeps them up-to-date on their favorite athletes, Super Bowls, World Cups, and how “Tom Brady is (finally) ready for Pickball.”
Gay, now in his 13th year as sports and humor columnist for the Journal, embarked upon his writing journey in Belmont Hill School in the suburbs of Belmont, MA, where he worked the school newspaper. His first experience with sportswriting was covering high-school and elementary school sports, traveling to events like the Little League Championships where he “interviewed ten-year-olds about their ground balls.” Writing was where he found his calling, and working the school newspaper cemented the notion, “This is it. This is what I want to do.”
Gay approaches his sportswriting much like a 10-year-old views life. Like a child’s favorite action TV show, Gay explains that sporting events also have heroes and villains, protagonists and antagonists, good guys and bad guys. He loves to search for untold stories. He favors stories of professional athletes who aren’t millionaires or on magazine covers, but those who are working second and even third jobs to pay their expenses, and training relentlessly to prove themselves.
Maybe his inclination to tell the stories of lesser known athletes comes from his “forgettable” career in baseball, basketball, cross-country and tennis. Gay is the first to acknowledge his shortcomings. He’s never going to climb Everest, be a rock star, or learn how to drive stick shift. But he is going to win an Oscar, he says, although he’s not sure for what. “Look for me on the stage. I’ve got my speech ready,” he says.
Similar to his favorite tennis players, Ons Jabeur, Carlos Alcarez, and Daniil Medvedev, Gay is always learning and getting better as a journalist. Gay views journalism in the same way professional athletes approach their sport: he’s constantly finding ways to improve and adapt to the changing world (or game). He’s incessantly striving to sharpen and improve his craft, just like Alcarez hitting tens of thousands of balls to practice his lethal drop-shot.
Gay attended the University of Wisconsin-Madison, where he credits his acceptance to one sleepy admissions officer. In the age before the internet, his first job in writing after college was in advertising for Martha’s Vineyard newspaper The Vineyard Gazette, where he would go door to door selling ads. From there, Gay got into the editorial side of things, working stints at the Boston Phoenix, New York Observer and Rolling Stone, before finding his way to GQ, where he served as article editor. When an opportunity to work at the WSJ came up in 2009, Gay quickly jumped aboard and has been there ever since.
Unlike his readers, Gay did not read the WSJ . . . until he started working there. Now, he loves The Journal. “It’s just been the best,” he says. He gets to write stories on a topic that most everyone enjoys: sports. His stories bring his readers an outlet of happiness and excitement in their often stressful day. He travels the world, from the immaculate grass courts at Wimbledon to the cobblestoned finish line of the Tour de France at the Champs Elysées. His job, as he describes it, is “embarrassingly fun.”
Gay is perfectly suited for his line of work. He genuinely likes to make everyone happy, whether it’s his readers worldwide or his homebound black-and-white tuxedo cat, Baxter, who Gay swears can talk. Gay’s skillful ability to intertwine humor and wit into his writing is rare.
Former CBS sports producer Tommy O’Neill, praises Gay’s rare finesse with words and stories. “Making readers laugh is a tough business,” says O’Neill. “But Jason makes it seem easy. His writing makes you chuckle.”
O’Neill is not the only one to recognize Gay’s talented craft. The Society of Professional Journalists named him Sports Columnist of the Year in 2010, 2016 and 2019. And his best-selling book, Little Victories, was a finalist for the Thurber Prize for American Humor.
In between his day job and school drop-offs and pick-ups, Gay recently released his second book, a collection of essays called I Wouldn’t Do That If I Were Me: Modern Blunders and Modest Triumphs (but Mostly Blunders). He reveals his subpar golf skills and spills his most sought-after parenting advice, like banging pots and pans and shouting “Bear! Bear! Bear!” to get your sleepy child out of bed in the morning.
In today’s smartphone, media-driven age, Gay says “Asking someone to read a book these days feels like asking them to join you on a sail from Maine to Portugal.” In a world full of distractions, getting someone’s attention, and keeping it, have become increasingly difficult tasks for the modern writer. That’s why Gay considered naming his book, “Hey, A**hole!” However, he reconsidered. His father-in-law can still beat him in a fight.
Just like the athletes he writes about, Gay is no stranger to a challenge. “You’re never a finished journalist,” he says. He’s always looking for ways to get better, sharpen his writing, and adapt to the changing world. Before social media, he told his inner thoughts to Baxter. But now, he tweets daily to his 80,000 followers.
After over a decade of covering sports at the Journal, Gay’s zeal for writing unwaveringly shines like his gleaming T2000 tennis racket. It’s aluminum, it doesn’t tarnish. He’s excited to cover the 2026 World Cup in Atlanta and the LA 2028 Summer Olympics. More than anything, he finds joy watching his children grow up.
He approaches his life with the same enthusiasm and warmth of his writing. “It’s the little things that build up over time. Be encouraging to peers. Be a good co-worker, a good boss. Empathetic to colleagues.” And with a laugh, he adds, “And notwithstanding today, be on time.”