At Nationals Park on Saturday, October 10, the air inside the stadium was charged with the kind of joy that only happens when sports and entertainment collide. The first-ever Banana Bowl had brought together the Savannah Bananas and five other teams in a spectacle that felt less like a traditional baseball game and more like a traveling carnival with a diamond at its center. In the stands, Maggie Sajak was living proof of that magic. The 31-year-old daughter of legendary Wheel of Fortune host Pat Sajak had come to cheer on her boyfriend, Jackson Olson, as he and the Savannah Bananas were introduced to a massive ovation. Her reaction was pure, unfiltered excitement. “Let’s go!!!!” she wrote on her Instagram Story, sharing footage of Olson taking the field. Later, as the evening’s musical guest of honor took over, she posted a video of herself dancing with abandon in the stands, captioning it with a mood that any fan of both baseball and boy bands could understand: “Mood when @jacksonolson and the Jonas Brothers are on the same field.” It was a moment so surreal that Sajak herself had to pause and ask her followers, “Like how is this real OMG?” For anyone who has ever watched the Bananas blend sportsmanship, comedy, and choreography, or who has watched the Jonas Brothers turn a stadium into a singalong, the question made perfect sense. This was not a normal Saturday night, and Maggie Sajak was clearly not going to let a single second pass without savoring it. Her social media activity painted a picture of someone deeply invested, not just in her boyfriend’s athletic performance, but in the entire joyful chaos of the event. The excitement she radiated from the stands seemed to mirror the energy on the field, where players were as likely to break into a dance as they were to turn a double play. And for Olson, knowing Maggie was out there, cheering louder than just about anyone, had to make the whole experience feel even more extraordinary.
The Banana Bowl itself was unlike anything baseball fans had ever seen. Six teams from the Banana Ball Championship League—the Savannah Bananas, Party Animals, Firefighters, Texas Tailgaters, Loco Beach Coconuts, and Indianapolis Clowns—gathered at Nationals Park in Washington, D.C., for a night of competition and entertainment. Each team brought its own personality and fan base, but for one memorable stretch in the ninth inning, rivalries were completely set aside. The Jonas Brothers took the field and transformed the diamond into a stage, performing a medley of their greatest hits that included “Burnin’ Up” and “Sucker.” Around them, players from all six teams joined in a choreographed dance routine, a synchronized celebration that blurred the line between sports and pop concert. It was a spectacle designed for the social media era, and it delivered. When the brothers then jammed on “Celebrate!” with Olson and his Savannah Bananas teammates at home plate, the moment felt tailor-made for everyone who loves both home runs and high notes. The star power extended well beyond the music, too. Kane Brown, John Cena, Pentatonix, the touring company of Disney’s Beauty and the Beast, and cast members from Dancing With the Stars all made appearances throughout the exhibition, turning the game into a variety show with baseball woven through it. Amid all that glittering chaos, however, there was still a competition to win. The Savannah Bananas fought their way to the final but ultimately finished as runners-up, with the 2026 Banana Bowl title going to the Texas Tailgaters. For Olson and his teammates, it had to sting a little to come so close to history; the Bananas had been the headliners, the team that made Banana Ball a phenomenon. But if Saturday taught anything, it was that Olson’s world had grown bigger than any one final score. His defeat on the baseball field would be followed by a very different kind of competition just days later, one where he would be judged not on batting averages but on samba rolls and salsa timing. And even in a stadium packed with celebrities and champions, the image that stayed with many fans might have been Maggie Sajak dancing in the stands, completely in love with the show and the man at its center.
That man, Jackson Olson, is currently living one of the most demanding double lives in sports and entertainment. At just 28, he is a key player for the Savannah Bananas, the exhibition baseball team famous for its rule-bending, fan-first approach to the game. But this fall, he has somehow added another full-time job to his plate: competing on Dancing With the Stars season 35. Balancing nightly rehearsals with Emma Slater, his professional partner, and game travel across the country would break most people. Olson seems to handle it with a grin, perhaps because he has a secret weapon waiting for him in every audience. Maggie Sajak has been a fixture in the ballroom since the season’s early weeks, sitting where he can see her—or, more accurately, where he can try not to see her. Their relationship is still relatively fresh in the public eye. The couple went public in April, but their origin story goes back a few months earlier, when they crossed paths at a Los Angeles Dodgers game in October 2024. What started as a chance encounter over baseball has become a full-fledged partnership, and this season has put that partnership to the test. Between cheering for Olson at Banana Ball exhibitions and watching him attempt everything from waltzes to cha-chas, Maggie has become a constant presence. She wears her support openly, whether that means posting excited Instagram Stories or donning a “Team Banana” ballroom shirt, a perfect sartorial mashup of her boyfriend’s two worlds. Olson, for his part, clearly treasures her devotion. Having someone who sees you first as a person, not a performer, matters in a space as glittering and high-pressure as a prime-time dance competition. The fact that Maggie’s family includes one of the most recognizable faces in television history only adds another layer, but Olson does not seem intimidated. Instead, he appears eager to embrace it all, with Maggie by his side and a busy schedule that would make most people dizzy.
There is a very specific reason Olson tries not to look at Maggie during his DWTS dances, and it is perhaps the sweetest detail of their relationship. In an exclusive sit-down with Us, Olson explained that while he loves having her in the audience, he cannot allow himself to meet her gaze in the middle of a performance. “It’s so awesome [to have her here]. I try not to look at her during the dance because I know that she’s smiling,” he revealed. “I know that she’s so excited and smiling. And if I looked at her, I would just like be like, ‘Ah!’” His reaction is a perfect mix of professional discipline and genuine affection. He knows his girlfriend so well that he can picture her face without even looking at her; he knows she’s beaming, proud, maybe even tearing up a little, and that knowledge is powerful enough to knock him off his carefully rehearsed footwork. It’s a relatable feeling, the moment you catch a glimpse of a loved one in the crowd and suddenly emotion overwhelms professionalism. Olson clearly wants to stay in the zone, but the fact that he has to actively avoid Maggie’s smile speaks volumes about how much it means to him. She is not just another face in the audience; she is the one person who could make him lose his composure with a single look. His partner Emma Slater probably appreciates that discipline, because a salsa is hard enough without your lead getting emotional mid-spin. At the same time, Olson was happy to share that Maggie fully supports the team, not just him. “But it’s awesome, and she’s so supportive of both of us, too. She was wearing the Team Banana ballroom shirt [for Viral Hits Night], so that was cool.” It was a small detail, but a telling one. Maggie isn’t merely Olson’s girlfriend; she’s part of the broader DWTS family, a cheerleader for the partnership between Olson and Slater. In a competition that can feel intensely personal, her presence makes the experience feel shared rather than solo. Olson’s words reveal a man who is grounded, grateful, and just a little bit in awe of the woman cheering for him.
As if Maggie’s support weren’t enough, Olson hinted that another famous Sajak might soon be joining the DWTS audience. Asked whether Pat Sajak—Maggie’s father and one of the most beloved game show hosts in television history—would make an appearance, Olson didn’t miss a beat. “We need to [have him here],” he insisted. “I think he’ll be at one of these.” That possibility adds an extra layer of significance to the young athlete’s already surreal fall. Pat Sajak stepped away from the nightly glare of hosting Wheel of Fortune after decades, but he remains a television icon. To have him in the ballroom watching Olson dance would feel like a symbolic stamp of approval, not just on Olson’s performance skills but on his relationship with Maggie. For a guy from the world of Banana Ball, being in the same arena as the father of the woman he loves, especially a father with Pat’s cultural stature, could be intimidating. Olson, however, seems to welcome it. His tone suggests he has been actively hoping for the visit, eager to show Maggie’s dad what all the fuss is about. The upcoming appearance would also complete a full-circle moment for the couple: they met at a baseball game, dated quietly for months, went public in April, and now are sharing their journey with millions of viewers on a Tuesday-night dance show. Having Pat in the audience would be a visible gesture of family support, a way of saying that the relationship is not just a fling but something real. It would also be a wonderful human moment: a former game show legend sitting in a ballroom, watching his daughter’s boyfriend dance the salsa to a pop song, surrounded by cameras and glitter. Olson seems ready for it. He knows that Dancing With the Stars is as much about heart as it is about technique, and a famous father-in-law’s nod from the audience would be the kind of moment that makes the whole whirlwind worthwhile.
The immediate focus, however, is firmly on the next performance. There will be little time for Olson to decompress from the Banana Bowl or to relive the joy of dancing alongside the Jonas Brothers. On Tuesday, October 13, he and Emma Slater will take the dance floor for “Super Bowl Night” on DWTS, delivering a salsa set to “Uptown Funk.” It is a fittingly energetic song for a player whose life has become a nonstop sequence of high-octane challenges: baseball games, talk shows, dance rehearsals, and now a televised performance with a football-themed night as the backdrop. Fans can watch Dancing With the Stars live on ABC at 8 p.m. ET, with streaming available on Disney+, which means Maggie won’t be the only one watching. Viewers across the country will see whether Olson and Slater can capture the same kind of spark that made the Banana Bowl so memorable. It will be a different kind of stage; no team, no bat, no home plate. Just two dancers, a song, and the pressure to make every step count. But Olson has already proven he can handle pressure. Whether he is in a stadium full of screaming fans or a ballroom filled with sequins and spotlights, he approaches every challenge with the same unpretentious energy that made Maggie fall for him. And Maggie will be there, of course, probably wearing another themed shirt, probably smiling despite her nerves, and definitely serving as the anchor he needs. Even though he won’t look at her during the dance, he will know she’s out there. Their 2026 season—if one can call it that—has been a blur of baseball, pop music, choreography, and romance. From that first chance meeting at a Dodgers game to the surreal spectacle of the Banana Bowl and now to the bright stage of Dancing With the Stars, Olson and Sajak have created something remarkable together. It’s a story that proves the best moments often happen when you least expect them: a game you didn’t plan to attend, a smile you can’t resist, and a partner who makes every impossible schedule feel worth it. The final score of the Banana Bowl may not have gone his way, but in the bigger game—the one where finding someone who cheers for you no matter what matters most—Jackson Olson is already a winner.
