Jackson Olson Passed on the MLB for College, but Still Dreamed of Going Pro. Then His Viral Videos Changed Everything (Exclusive)

In about 95 seconds, baseball player Jackson Olson captured what it felt like to spend years of his childhood playing catch with his father Dan, prioritizing the ritual even as life pulled them in different directions.

But their story, or at least the surprise ending of his social media video, included an experience many fathers and sons showing up for weekend Little League practice would be jealous of — a session of catch at Fenway Park.

The experience at the storied stadium was “any kid’s dream,” Dan tells PEOPLE — although he insists he’s still a Yankees fan.

Jackson is an infielder for the Savannah Bananas, an independent Georgia-based baseball team in which “a circus breaks out in the middle” of games, he says. Players show up wearing plaid kilts and break into dance routines throughout the games.

“The entertainment is obviously very important and made us who we are,” he says, as a fellow player pops his head into the frame of the video call and grins in the background. “But it’s the trick plays and the home runs and the hits that people are now kind of coming to see.”

Until he was a teenager, Jackson’s dad coached his baseball teams. Growing up as the coach’s son, he carried the weight of pressure and expectations, heartened by his father’s leadership.

“I proved myself on the field, but also knowing that my dad treated every single kid, no matter what, no matter where they came from, their background, how good they were at baseball — [he] didn’t care,” Jackson recalls. “He always made sure to make them feel loved and to make them feel like they had a spot on our team.”

Reflecting on the evolution of the sport, Dan notes spending extra cash on travel leagues doesn’t always correlate with future advancement.

“I think one of the things that Jackson has done a great job of, has kind of told the story that you don’t need to spend all this money, somebody will find you,” Dan notes. “Somebody will see that you’re talented, whether it’s a college recruiter or a pro scout. They’re going to know.”

“I mean, if you’ve got it, you’ve got it. And some people, I think, anticipate that their son or daughter is going to get a lot more opportunity because they spend this money on travel sports,” he adds. “There’s nothing wrong with travel sports. It’s just I think there’s some false promises that are made out there that parents really need to be careful of.”

During college, Olson declined an offer from the Arizona Diamondbacks in order to complete his degree, but then MLB’s draft was shortened in the wake of the pandemic, shifting his options to keep playing after school.

He transferred from the University of Hartford to Stetson University, where he was able to play an extra season due to NCAA eligibility extensions for athletes whose spring seasons were upended by COVID-19.

A series of social media videos changed the course of his career, catching the eye of Savannah Bananas owner Jesse Cole and landing him a trial run with the team before he was officially added to the roster.

“[Cole] reached out to me and was like, ‘Hey, come, play six games with us. Let’s see how you do.’ And now I’m here,” he says, noting earlier, “the rest is history.”

Olson’s parents now travel to attend many of his games, squeezing in family time in some of the quieter moments. His catch session with Dan this season came during the Savannah Bananas’ stop at Fenway Park in early July as part of the Banana Ball 2025 national tour.

“We’re just really proud of Jackson, and a lot of it was timing, but more so, it was really his skill, his ability, and just making that connection,” his mom Laura says. “And he’s so genuine. And that’s the one thing that I’m especially proud of is that he’s stayed true to himself.”

Now, the 27-year-old is hoping to use the same social media skills that helped him land the job to create videos with relatable content that might draw families closer together, mixing in a bit of the humor he carries onto the field.

“I think people crave the relationships that I have with my parents, with my teammates, my friends,” Jackson says. “Everybody wants to find their purpose. They want to find their people.”

“I try to inspire people, inspire parents, inspire kids to have the same relationship that we do,” he says.

Sometimes, he’s prone to test the limits of those relationships with practical jokes, recently pranking his mom and telling her he was going to appear on the next season of ABC’s The Bachelor and informing her he’d need to get married at the end of the show.

“What if you don’t find the right one? What if you don’t pick the right one?” she asked.

The video, especially the marriage aspect, were only supposed to be part of a bit when he posted it back in May. But then The Bachelor came calling. Olson says representatives from the hit series have since requested a self-tape.

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“He’s always doing things like that to me,” Laura says with a laugh, adding that she finds levity and positivity in his videos.

“The message has always been the same. He hasn’t wavered with that, and I look back sometimes to his earliest TikToks, and the message is still, it’s still there. So that’s something to be really proud of,” she adds.

“Who knows if I’ll do it, or if they choose me to do it,” Jackson says of The Bachelor. “But it just all stems from me having fun on social media, and I’m going to keep doing that.”