Growing up, when Jimmy O’Brien’s two sisters held a back-yard contest to determine who was more athletic, O’Brien, then a high-school student in suburban Connecticut, did the reasonable thing: he egged them on. The following year, he decided to make the Sister Olympics, as the family came to call it, a little more formal. He created the competitions, designed costumes, and got a referee’s shirt for his dad. O’Brien and two of his best friends, Nick and Jake, split play-by-play and spectator duties. He even rigged up three cameras to document the event, then edited the footage into a movie.

O’Brien loved games, and he loved making videos. When the family settled in Connecticut, after years of bouncing around, he had one request for the new house: a big enough back yard for Wiffle ball. One of the first things that he did after they moved in was paint two trees yellow, to make foul poles. He got his first camera in seventh or eighth grade, and took it with him everywhere. It was the heyday of reality-TV shows like MTV’s “The Real World” and “Jackass.” Everything was content. O’Brien wasn’t filming strangers’ interpersonal dramas or deadly stunts, but he realized, early on, that part of the fun of any experience is in the narrative, the way it’s retold.

O’Brien’s mother suggested that he use a pseudonym for a social-media handle, in case future employers decided to look him up. He went with “Jomboy”—an iPhone’s autocorrect of “Jimmy.” It was reasonable advice, if there’d been any employers to worry about. But after drifting through a series of colleges on his way to a degree, O’Brien mostly worked gig jobs. In the Bay Area, where he lived with his girlfriend (now wife) and served as a wedding videographer, he looked for a sense of community through his other great love: the New York Yankees. His mom was from the Bronx, and he’d grown up in New Jersey until he was eight. Wherever he was based, the Yankees, in an important sense, represented home. In 2017, O’Brien started a podcast, “Talkin’ Yanks,” all about the team, with his best friend, Jake Storiale, whom he’d met in Connecticut through baseball.

At the same time, O’Brien made short, funny videos about Yankees-related episodes: a brawl with the Detroit Tigers, a team picture of players with their thumbs down. But what really launched Jomboy Media, in 2019, was O’Brien’s breakdown of a rant at an umpire by the Yankees’ skipper Aaron Boone. O’Brien, who had a knack for reading lips, deciphered what Boone was saying and then captioned it in a video for social media: the Yankees, Boone said, were “fucking savages in the box.” The post went viral; before long, you could buy T-shirts quoting the tirade on the “Talkin’ Yanks” website. A few months later, O’Brien uploaded another video that broke down a sign-stealing scheme by the Houston Astros’, pointing out the sound of a banging trash can. Millions saw it, and then flocked to him for more. These “breakdowns” of hot mikes, ejections, and other high emotional moments eventually became a hallmark of Jomboy.

O’Brien was lucky, in a sense, that his presence back then was still pretty small. For a long time, Major League Baseball had a hard stance on copyright, claiming revenue from videos and forcing some non-licensed accounts to take the content down. O’Brien received his own share of letters from the league’s lawyers. Other leagues, particularly the N.B.A., were making cultural inroads in ways that M.L.B. was not. Eventually, the league started to see that influencers like O’Brien were gaining the young followers that the league wanted.

He may have been lucky, too, that he wasn’t too young himself. By his late twenties, O’Brien told me, when Jomboy’s audiences started to grow, he understood his voice and had no interest in the kind of easy attention that came with being controversial. “I think if I had started younger, it’s probably easier to try and be angsty or edgy,” he said. His company is often described as upbeat and light, the anti-Barstool—a reference to the popular personality-driven sports-content company known for being abrasive and sometimes outright offensive. There’s something to that. O’Brien will stop himself from doing a video if he reads someone’s lips and sees anything said that might genuinely get them in trouble. Recently, he quashed an idea to make merch quoting something that an injured Yankees’ catcher said, which sounded funny out of context but was part of a sad, longer quote. O’Brien isn’t interested in causing fights, but he’s also careful not to sound sanctimonious. He curses. He still likes reality TV. He enjoys content from companies that engage in all sorts of “nonsense,” as he puts it. (“I gobble it up,” he said.) He has built his career around “mostly covering people who are losing their minds, screaming and cursing and probably doing something they’re embarrassed of.” But he’s never forgotten that part of the fun of any story is in the retelling—and everyone, even the guy who’s losing his mind, likes to be in on the joke. The subjects of his videos generally “seem to get a kick out of it,” he said. So do increasing numbers of other people, even if they don’t consider themselves baseball fans.

O’Brien’s older sister, Courtney Hirsch, observed her brother’s fledgling media company with both pride and, as a businesswoman, a certain itch. Hirsch had followed a more traditional route than her brother and had become an ad-sales executive at Uber. She knew that ads were the quickest way to monetize content creation, and she was convinced that her brother and Storiale could be doing better. In 2020, O’Brien put out a feeler, through their mother and father, to see if Hirsch would help out. She responded that she’d only do it if she were fully committed. “I’m a very all-or-nothing person,” she told me. Before long, she became Jomboy Media’s C.O.O., and then, in March, 2025, the C.E.O. The company now has sixty employees (including O’Brien and Hirsch’s youngest brother, Luke) and is projecting revenues to surpass twenty million dollars this year—double what they were just two years ago. Last year, M.L.B. bought a minority stake in the company for an undisclosed sum, as part of its efforts to generate new fans.

Is that campaign working? Maybe so. In the past few years, baseball has felt more widely popular, and there are numbers to back it up. Partly, the league has leaned into the international demographics of its players to cultivate a more global audience. The final of the World Baseball Classic, in which Venezuela defeated the United States, was watched by nearly eleven million people on Fox and Fox Deportes, more people than the average audience for the 2025 N.B.A. Finals. Last fall, the World Series, between the Los Angeles Dodgers and the Toronto Blue Jays, recorded its highest average viewership (15.7 million) since 2017. The Dodgers’ generational superstar, Shohei Ohtani, is the rare type of athlete whose name is known by non-sports fans. And the league’s revenues are at a record high—in part because of its active efforts to engage younger viewers, after years of dealing with the perception that baseball was too old and too outdated to survive.

Sometimes it seems like baseball isn’t doing itself any favors. For instance, there is endless talk of how the sport is too slow. “I like baseball because it’s slow,” O’Brien said. It moves at a conversational pace. It gives you time to think and talk about things. “The secret is that Americans like slow sports,” he argued. Other countries followed games that moved continuously—soccer, rugby. But even football games are mostly spent standing around. The stoppages allow for weird moments of drama and the emergence of characters. Jomboy is friendly to stats, but it makes narrative-driven videos, accessible to baseball fans and non-baseball fans alike.

There are many videos that don’t just involve baseball content: breakdowns of volleyball, pickleball, “Wheel of Fortune.” Anything goes. After watching a lot of cricket in the middle of the night while on paternity leave, O’Brien started posting cricket videos. Jomboy Media is now working on a partnership with Republic Bank Caribbean Premier League. After some videos of blitzball in an alley got good views, Jomboy rented a warehouse and started staging elaborately produced Warehouse Games, featuring blitzball and croquet and other semi-invented or tweaked back-yard games, with uniforms and commentators—the Sister Olympics all grown up.

There are currently fourteen creators at Jomboy—eleven that work from the company’s midtown Manhattan office, in addition to the prominent sports broadcaster Chris Rose, the former M.L.B. player Trevor Plouffe, and O’Brien himself. The Yankees manager, Boone—he of the “savages” rant—is a regular guest on “Talkin’ Yanks.” It is always hard, of course, to hold onto something authentic while scaling up, particularly when the internet, the basis of the company’s community, is not very nice anymore. Jomboy employees have made a few mistakes themselves. But being basically decent is good business, O’Brien argues. “It’s very easy to get hate views and to get rage views,” he said, “but no one buys hate merch. No one goes to a show if they hate you. No one supports your next venture if they’re not on your side. So it’s empty views, and it’s easy views. There’s no challenge in it, and there’s really no long-term reward, so we don’t try to do that.”

For now, at least, the audience seems forgiving, which lets Jomboy try new things. Sometimes it works. And sometimes it’s opening night, and the Yankees game is on Netflix for some reason, and the Jomboy live stream shows three grown men, sitting in recliners, eating giant lollipops. “You look like a lost boy,” O’Brien cackled, as Storiale pulled his Yankees cap low and took a lick. He meant “lost” as in “disoriented,” but my mind flashed to Peter Pan. A lost boy indeed. But there are worse things to be. ♦