Jimmy O’Brien (“Jomboy”)

The Jomboy Breakdown

Jimmy O’Brien, better known to sports fans as Jomboy, grew up in an average New Jersey household. He was raised in a loving family but struggled with a speech impediment. The difficulty made him self-conscious, but he eventually overcame it with flying colors. His family moved often, from Australia to Illinois, then back to Connecticut and eventually settling in New York City, where the Yankees became a part of the family’s identity—”a root, or a home,” in his mother’s words. Jimmy’s deep love for the team would become foundational to his future career.

Jimmy graduated from Central Connecticut State University with a history degree—in his own words, he graduated “near the middle” of his class. Like many young adults, he struggled to figure out the direction of his life and what he wanted to do. After a series of failed attempts to break into some sort of a career path—Jimmy was left wondering what he was truly meant to do with his life. He felt lost.

But even amidst the confusion, one thing was certain: he was creative and had a passion for videos and editing. This skill was obvious to his mother, and she encouraged him to pursue what he loved. Little did she know that it would propel him to achieving the American Dream.

Using His Love of Video Editing

Jimmy O’Brien has always been fascinated by the power of video. He would even produce hour-long documentaries of the road trips he would take with his friends; he was always the camera guy, and his editing skills were entirely self-taught, thanks to YouTube tutorials and good old-fashioned trial-and-error.

He had a blast making highlight tapes for his younger brother’s Little League team and would make videos for players hoping to land college scholarships. His first taste of some viral success came in 2015 when he made a video called “Scaring My Mom with a Fake Dog.” And yes, it was exactly what the title suggests. He sold the video for $4,000 and even got an interview on Japanese television—probably not the result he expected. It was a nice little success but still wasn’t the breakthrough that would bring him to where he is today.

By 2017, Jimmy started the Talkin’ Yanks podcast to connect to his Yankee roots. The show began as casual discussions about the MLB team but picked up steam as Jimmy’s personality and unique style was noticed. Jimmy was eventually joined by his friend Jake Storiale, who became a co-host. The friends managed to land an advertising agreement later that same year. It wasn’t much longer that the podcast was offering full-time work for Jimmy and Jake.

But the podcast wasn’t necessarily bringing in a full-time income. Jimmy had to scrape by, but he treated the podcast like a legitimate business. “I told my girlfriend like, ‘Hey, this is my job right now. It doesn’t matter that there’s no income right now. If I don’t act like there is, then there will never be.’”

Skyrocketing Success with the Astros’ Sign-Stealing Scandal

In November 2019, Jimmy’s life and career changed practically overnight. Following a report by The Athletic that revealed the Houston Astros’ were stealing signs in the 2017 MLB season, Jimmy uploaded a video with his own personal analysis of the situation. With game footage, he showed plainly that pitches were correlating with banging heard from the Astros dugout. Someone in the dugout would hit (or not hit) a trash can before each pitch, signaling the pitches to the batter—and the cheating wasn’t just in that one game. The video went viral, to say the least, propelling Jimmy into the limelight and giving him an enormous boost to his credentials.

Jimmy’s ability to break down sports controversies, plays, and intricacies (particularly in baseball) with profound insight and a generous sprinkling of humor resonated and continues to resonate with countless sports fans. Clearly, he wasn’t just some guy making videos. He had a valuable perspective to offer.

From there, Jimmy began cranking out his “Jomboy breakdowns,” most of which haven’t been quite as sober as a cheating team winning the World Series. Many of his breakdowns center around humorous exchanges between players, managers, and umpires. Jimmy began expanding his reach beyond baseball to other sports like cricket and lacrosse. He even did a breakdown of Will Smith slapping Chris Rock. Jimmy’s personal brand of humor—“fun, not funny,” as he describes it—has made Jomboy Media a go-to source for lighthearted yet incredibly insightful sports commentary.

Why Is He Called “Jomboy”?

Naturally, you want to know. The story is pretty simple: a friend texting him meant to type “Jimmy,” but, strangely, the name was autocorrected to “Jomboy.” It started out as an inside joke and eventually became a Twitter handle and then Jimmy’s brand. Now Jimmy is known far more by this interesting nickname than his real name.

Building Up Jomboy Media

What started as a passion project quickly grew into a full-on media company—Jomboy Media. In just a few years, Jomboy Media tripled its workforce; it now has a little over 60 employees. The company’s YouTube channel now has nearly 2 million subscribers, and their presence on other platforms, like Twitter, is far far greater. By 2021, the Jomboy Media had secured millions of dollars in funding with investors, including athletes and celebrities. They also expanded to nearly two dozen different podcasts under the Jomboy banner, including the flagship Talkin’ Yanks.

But even as Jomboy Media grew and grew, Jimmy and his co-host Jake Storiale have remained committed to the undertones that fueled their success: good vibes only. They make their content in the spirit of being “fun” rather than “funny,” and they’re very intentional about avoiding the kind of mean-spirited hot takes that too often saturate sports commentary. It’s a laid back, relatable, but still well-informed approach.

In 2023, Jimmy signed a partnership with YES Network (Yankee Entertainment and Sports), which broadcasts Yankees games, further solidifying Jomboy Media within the sports industry. But despite the fame and the financial success, Jimmy O’Brien remains grounded. “I would never call myself a reporter,” he says. “I’m still just a biased fan. And I don’t plan on changing.”

Realizing the American Dream through America’s Favorite Pastime

Jimmy O’Brien started off as just a normal guy, an aimless young kid with no idea of how to move forward and make a living. But he had interests, passions, and talents, and a strong will to learn everything he could to make a living doing what he loves. And his enormous contributions have made the game of baseball more relevant for a whole generation of young Americas. What could be more of an American Dream than bringing America’s pastime to the hearts of so many? Jimmy didn’t take the traditional route to success. He didn’t climb a corporate ladder. He didn’t land a big executive job or become the majority owner of a sports team (perhaps someday he will). Instead, he found a way to turn his creative hobby into a thriving business.

Jomboy’s story reminds us that success can often come in unexpected ways. And it also shows that even when the path forward isn’t clear, it never hurts to chase a dream or a passion. For Jomboy, it wasn’t about finding a career—it was about sharing his passion for baseball and connecting to his Yankee roots. And for him, at least, that was enough.