MLB’s Jomboy Deal Shows Full 180

On Tuesday, MLB and Jimmy “Jomboy” O’Brien announced that the league would buy an undisclosed minority stake in his eponymous media company. It was a major win for Jomboy Media, which the league had previously held at arm’s length—or further.

O’Brien first became a household name to baseball fans in July 2019, when he used a combination of lip-reading skills and MLB’s ambient field microphones to get inside a spectacular ejection. Yankees manager Aaron Boone, caught on audio expertly picked up by Jomboy, berated fill-in umpire Brennan Miller.

“My guys are fucking savages in that fucking box!” Boone screamed at Miller. “And you’re having a piece of shit start to this game—I feel bad for you, but fucking get better!”

The video launched Jomboy into viral fame, gave Yankees fans a slogan and bootleg merch for a solid year, and was a rare glimpse of a personality for the normally staid Boone. 

Naturally, MLB and its most famous team were unhappy that O’Brien had such a knack for isolating its feed audio.

“It wasn’t supposed to be that clear,” Joe Torre, then MLB’s chief baseball officer, said at the time. “It shouldn’t happen… When it starts getting personal, that’s dangerous.”

Yankees spokesman Jason Zillo admitted to ESPN at the time that the videos were “growing the game,” but he worried that “that’s some really treacherous, dangerous ground that could be really personally damaging to a player, and also for the team—and for the league, for that matter.”

Six years later, Jomboy—now a full-fledged media company—has won something like a total victory with the MLB deal. He already struck deals with the Yankees in 2022 and 2023 that led to weekly segments with Boone.

MLB kept fighting arguably its most famous YouTube personality right up until taking ownership in his company. 

On a stream Tuesday morning, O’Brien said he had a deal lined up with ESPN last year to do regular Baseball Tonight segments, plus Home Run Derby and All-Star Game alt-casts, before MLB stepped in. 

“MLB had to protect their partners, and we weren’t [a partner],” and so “a door got gently shut,” he said. That led him to begin considering selling a stake in earnest. (He also said Tuesday that MLB was not injecting new capital into the company, just buying out existing investors.)

Even as his videos grew in popularity and a vibrant YouTube ecosystem continued to grow around baseball, MLB had yet to fully embrace it. In a May 2024 video, O’Brien detailed how the league would annually send out mass notices of copyright violations to him and other creators. “They’re a little egregious with the sweeps,” he said at the time. 

A source familiar with Tuesday’s deal said it would completely clear Jomboy’s channel to use MLB footage.

If Jomboy wins financially, and the league wins culturally, that leaves two groups who might still not love Tuesday’s deal. 

The first is MLB umpires, whose viral foibles helped make O’Brien famous in the first place, and whose errors he continues to document regularly. 

Dan Bellino, a longtime MLB ump and the president of the umpires’ union, said that while the union was not given a heads up about the deal, he was a Jomboy fan.

“As umpires, we welcome this partnership and the opportunity it brings to showcase the game’s complexity, including the vital role of officiating, through a new and dynamic lens,” he told Front Office Sports in an email. “I’ve always found Jomboy’s approach to be unique and entertaining.” Bellino added that the deal showed MLB’s “recognition of how today’s fans enjoy the sport.”

The second is Jomboy fans, who might understandably worry about a league-owned outlet neutering the content. O’Brien played a major role in documenting the Astros cheating scandal, for example, and is often critical of managers and teams on social media. 

The MLB deal explicitly says the league has “no editorial control or oversight,” and O’Brien spent much of Tuesday morning insisting on the point.

“What does this mean for the content? Nothing,” he said. “MLB wants us to continue exactly what we’re doing; they don’t have any creative control—more of a basic understanding that we carry the sentiment to not piss people off.

“They trust our tone,” he continued. “They don’t want it to change, and they don’t want it to feel like it’s changed. It actually says in writing, in the contract, that we will be maintaining and doing everything we have been doing.”

At the same time, it sounds like baseball has been given some assurance that it has a line into the Jomboy Media office to complain. 

“There’s really just a mutual understanding of, hey, if we do something you don’t like, you tell us,” O’Brien said. “And we’ll take that into consideration moving forward, and do a better job not pissing people off.”