On ‘Dancing With the Stars,’ Jackson Olson Takes His Biggest Swing Yet

Jackson Olson’s season with the Savannah Bananas finally ended on Oct. 10. And thank God it did.

Prior to that, the 29-year-old athlete was balancing his baseball responsibilities with his ongoing run on ABC’s Dancing With the Stars, where his love of performance, knack for social media and generally sunny disposition have carried him to Week 7 of the 11-week competition.

The initial back-and-forth was quite tiring, to say the least. Olson was juggling both activities for at least a month, from the show’s premiere on Sept. 15 to the end of the Banana Ball campaign earlier this month. At one point, he and dance partner Emma Slater took a red-eye flight from Los Angeles to Savannah, where they played and performed in a 7 p.m. Bananas game before flying back to the West Coast in time for an 8 a.m. dance rehearsal.

A more introverted athlete might find himself collapsing (or perhaps peeling, if you can forgive such an obvious pun) under the pressure, devastatingly susceptible to the effects of such demanding public pastimes. Olson, however, often classified by fans as the human version of a genial golden retriever, happens to be having the time of his life. And that has made all the late nights and early mornings well, well worth it.

“It was always, like, this is the most fun thing ever. This is just a special time. It's a fleeting moment. It's going to end in three weeks, a month,” he says. “And so I think that kept me going. If it was a [year] of doing [both], I would have to figure out some ways to keep myself sane. But I think just eating healthy and getting eight hours of sleep was all I really needed to do.”

It also helps, of course, that the infielder grew up dreaming about a life like this, yearning for a stage brighter than the one he was on. Following a collegiate baseball career that saw him flirt with but ultimately fail to break through to the majors, Olson hung up his jersey and moved to Los Angeles, where he made ends meet delivering groceries on Instacart. More for fun than anything, he began posting on TikTok, and, to his surprise, amassed an unexpected audience amused by his mid-aisle antics and goofy personality. That success later led to a content gig with Major League Baseball, and eventually, his life-altering stint with the Bananas. Now, for a professional athlete with a soft spot for crowd-pleasing and showmanship (plus a healthy Disney obsession on the side), Dancing With the Stars was simply the natural next step.

“I kind of manifested this whole thing and posted a couple TikToks last year just joking ... never thinking that it was a possibility,” he told Good Morning America in May, when his casting was first announced. “But when I posted it, I’m like, ‘Maybe there is a possibility.’ I saw some comments, I’m like, ‘OK, maybe this is possible.’”

Less easy to manifest, however, has been the technique. Indeed, like the majority of contestants who twirl through Television City Studios, the art of ballroom has proven challenging for the second baseman, who is much more comfortable hitting the Renegade than a rumba.

“I think staying in frame is the hardest thing that I’ve had to do. Because having good posture is not a thing in baseball. You don't have to have good posture in baseball. You actually have to have bad posture in baseball,” he says with a laugh, adding that the resulting pain in his arms isn’t something he is used to, either.

But he also says he feels the “strongest I’ve ever felt” entering Week 7 of the 11-week experience, and has lost a whopping 23 pounds since the show’s start—not quite “blowing away with the wind” territory, he quips, but a testament to his hard work, at the very least. His Bananas background has come in handy in unexpected ways, too.

“I think because of the Bananas and because of the characters I've played, it's easy for me to get into character,” he says. “The technique is the hard part. That's where I'm really having to try to dig deep into another part of me I never thought was there.”

For the modern contestant, DWTS is a battle waged as much inside the ballroom as it is online, where a near-constant stream of social media content is essentially a prerequisite for all pairings. And as helpful as this can be to a couple’s success—on social media, dancers can essentially appeal to viewers’ hearts and minds directly—it also becomes yet another box to tick, another bit of homework, another thing to learn that, like dancing itself, might come more naturally to some than others.

Thankfully, Olson happily finds himself comfortably in the former camp.

“That's the most fun thing,” he says of the show’s content mandate. “I don't even see that as a job at all. They told me coming in, ‘You're going to have to post a lot.’ Emma's like, ‘I want to post like two or three times a day.’ I'm like, ‘That's fine.’ That's what I love doing.

“I love thinking of ideas in the morning and bringing them to Emma or texting her a thousand messages. She probably gets so annoyed.”

For this week’s “Horror Movie Night,” Olson and Slater will dance a contemporary routine to Frank Sinatra’s “That’s Life,” a nod to Todd Phillip’s Joker. But scarier still is what will happen after the final performance of the evening: a double elimination, which means double the odds he is sent packing. Assuming he is safe, he must still survive Disney Night, Grammy Night and the semi-finals to make it to the finale, scheduled for Tuesday, Nov. 24.

Whatever happens, though—whether his experience is cut short, or whether he quicksteps all the way to the end—he will continue to chase his joy in whatever he chooses to do next (banana ball included, of course).

“I'm definitely living in the moment,” he says, before citing hosting as a possible avenue to explore down the line. “I'm taking a lot of advice from Jesse Cole, the owner of the Bananas, and he always says, ‘Follow your energy.’ He's told me that since day one—follow your energy wherever it's taking you right now.”

Watch out, world—this is a showman with a lot of it.

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