Jackson Olson built his fame one viral clip at a time, and that is why his story feels different. The Savannah Bananas star went from a college infielder posting TikToks in a mirror to a national TV contestant on Dancing with the Stars. Here is the full picture of who he is, where he came from, and what is driving his rise in 2026.
| Field | Details |
|---|---|
| Full Name | Jackson Daniel Olson |
| Nickname/Stage Name | Jackson Olson |
| Date of Birth | October 6, 1997 |
| Place of Birth | New Milford, Connecticut, USA |
| Age | 29 years (as of October 2026) |
| Nationality | American |
| Zodiac Sign | Libra |
| Profession/Occupation | Baseball player, entertainer, content creator |
| Years Active | 2022–present (Savannah Bananas) |
| Education | New Milford High School; University of Hartford (marketing); Stetson University (master’s in business marketing) |
| Genre/Field | Banana Ball, sports entertainment, social media |
| Dating/Relationship Status | Dating Maggie Sajak (public since April 2026) |
| Parents | Dan Olson and Laura Olson |
| Siblings | Older brother Alex, older sister Ari |
| Notable Works | Savannah Bananas infielder (No. 8), Dancing with the Stars Season 35 |
| Awards/Honors | University of Hartford Anchor Award (2023) |
| Social Media | TikTok and Instagram (@jacksonolson_) |
Who Is Jackson Olson?
Jackson Olson is an infielder for the Savannah Bananas, the touring team behind Banana Ball, a fast, fan-first version of baseball packed with choreography and trick plays. He wears No. 8, bats left, throws right, and is one of the most recognizable faces on the roster.
What separates him from most athletes is the way he became famous. He did not climb through the minor leagues. He built an audience online first, then turned that audience into a career. Today he has more than two million TikTok followers and over one million on Instagram.
In 2026, he took that crossover appeal to ABC as the first Savannah Banana ever cast on Dancing with the Stars. That move put him in front of an audience that may never have watched a baseball game, which is exactly the kind of growth the Bananas brand thrives on.
Jackson Olson Age, Birthday and Early Life
Jackson Olson’s age is 29. He was born on October 6, 1997, which makes him a Libra, and he celebrated his 29th birthday in the middle of his DWTS run. Many fans are surprised by this, since his playful on-field energy reads younger.
He grew up in New Milford, Connecticut, a small town where he played baseball, football, and basketball at New Milford High School. As a senior baseball captain, he hit .464 and earned First Team All-State honors, a clear sign he had real talent long before the dancing started.
Sports ran in the house. His father, Dan, played college basketball and taught Jackson much of what he knows about the game. That early mix of family support and competitive drive shows up in nearly every chapter of his career that followed.
Jackson Olson’s Family and Parents
Jackson’s mom is Laura Olson, a former special education teacher, and his dad is Dan Olson. He also has two older siblings, brother Alex and sister Ari. Ari is married to Zach, who, in a fun family twist, was originally Alex’s friend.
His bond with his mom became a public moment on Dedication Night, the October 20 episode of DWTS. He dedicated his quickstep to “L-O-V-E” by Nat King Cole to Laura, and she joined him and Emma Slater on the ballroom floor during the live show.
Before the episode, he shared rehearsal photos and a heartfelt note on Instagram. He thanked her for supporting him behind the scenes for 29 years and said it was finally her turn to shine. He also showed off a hot pink tux and joked about living out his Broadway dreams with her.
Moments like this explain a lot about his public persona. From what I’ve seen covering creator-athletes, the ones who last tend to have a steady family base, and Jackson’s parents have clearly been his loudest fans from little league to live TV.
College Baseball at the University of Hartford and Stetson
Jackson spent four seasons as a Hartford Baseball player at the University of Hartford, where he majored in marketing. He appeared in 161 games and started 146 of them, which shows he was a reliable everyday player, not a bench name.
His biggest college highlight came with the 2018 team, which won the program’s first America East Championship and reached the NCAA tournament. He has described that run as a turning point that set the tone for Hartford baseball history.
After his junior year, he played in the Cape Cod League with the Hyannis Harbor Hawks and drew interest from MLB teams. Then COVID-19 hit in 2020, the draft was cut down to fewer rounds, and he went undrafted.
Instead of quitting, he used his extra year of eligibility at Stetson University, where he earned a master’s in business marketing and played for the Hatters in 2021. That marketing background quietly explains how well he understands building a personal brand.
How He Joined the Savannah Bananas
The path from college to the Savannah Bananas was anything but direct. After school, he moved to California and delivered groceries for Instacart while posting baseball content on TikTok. Those videos eventually caught the attention of MLB, which brought him into its creator program.
His growing social media presence then got him noticed by the Bananas. He joined the team in 2022 expecting to play just six games. Instead, he kept coming back season after season, and he is now one of the faces of the franchise.
Here is a quick look at how his career unfolded:
| Year | Milestone |
|---|---|
| 2018 | Part of Hartford’s first America East Championship team |
| 2020 | Graduated from UHart; went undrafted after the shortened MLB draft |
| 2021 | Played at Stetson while earning his master’s degree |
| 2022 | Joined the Savannah Bananas |
| 2023 | Received the Anchor Award, UHart’s top alumni honor |
| 2026 | Cast on Dancing with the Stars Season 35 |
He also returns to Connecticut to speak with young players and students. His message is simple and earned: follow your passion, even when the traditional path closes. Coming from a UHart alum who once stocked grocery orders, that advice lands with real weight.
Jackson Olson’s Dancing With the Stars Season 35 Journey
Jackson was paired with pro Emma Slater for Season 35, and the premiere aired in mid-September 2026. Since the show films live on Tuesdays in LA, he has had to juggle long daily rehearsals with Bananas games and constant flying, a schedule that would break most athletes.
He opened the season with a fittingly banana-themed routine and quickly became a crowd favorite. In Week 2, his song was changed just hours before the show, yet the couple still delivered one of the best performances of the night.
| Week | Theme | Highlight |
|---|---|---|
| Week 1 | Premiere Night | Banana-themed routine to launch his run |
| Week 2 | Viral Hits Night | Song changed hours before airtime |
| Week 3 | Yacht Rock Night | Social media controversy began after this episode |
| Week 4 | Mariah Carey Night | Waltz to “Without You” |
| Week 5 | Super Bowl Night | A tough night that put him near the bottom |
| Week 6 | Dedication Night | Quickstep to “L-O-V-E” with his mom, scored 32/40 |
On Dedication Night, judge Derek Hough said the quickstep was a strong step in the right direction but told him to watch his frame. The 32 out of 40 kept him safe and showed visible growth from a guy whose dance experience came from baseball fields, not ballrooms.
He has also admitted he cannot look at his girlfriend in the audience while dancing, because it throws off his focus. That honest, slightly goofy charm is a big reason viewers keep voting for him.
What Did Jackson Olson Say About Guillermo?
Jackson Olson’s comment on Guillermo Rodriguez came after Week 3 of DWTS. Banana Ball team the Loco Beach Coconuts posted a video of one of their players recreating Rodriguez and Witney Carson’s foxtrot on the field, and Jackson praised the copy in a way many fans read as a dig at the original.
His comment highlighted that the athlete had only rehearsed for two hours, which implied the recreation outshined the real routine. Viewers called it distasteful, especially since Rodriguez had been visibly improving each week and was a fan favorite in the ballroom.
The backlash moved fast. Fans called him a bully, and some said goodbye to him on social media. Prediction market odds of him being sent home jumped to 43%. He deleted the comment soon after, but screenshots kept the conversation alive.
The Apology and Making Up With Guillermo
On October 6, Jackson posted a public apology, telling Rodriguez and fans he was truly sorry his comment had created so much negativity. He took responsibility, said he cared about Guillermo, and made clear there was no excuse for how it landed.
He paired the apology with an Instagram reel of the two dancing together to “Nobody’s Perfect” by Hannah Montana. It was a smart, light way to smooth things over without brushing off the mistake.
Jackson also said they talked in person on set after the show and called themselves true friends. Rodriguez confirmed there was no grudge, described Jackson as a good guy, and said they were simply enjoying the competition together.
Was Jackson Olson Actually Canceled?
No, he was not. On October 11, Jackson posted a TikTok joking about “getting canceled,” using the word as a self-aware caption rather than describing any real consequence.
There was no formal sanction or penalty from the show, and he stayed in the competition. The joke reflected his athlete mindset: take the loss, learn from it, and focus on next week’s brand-new dance.
Jackson Olson’s Teeth: The Story Behind His Veneers
Jackson Olson’s teeth are veneers, all of them. After the Season 35 premiere, curious fans kept asking, so he answered directly on TikTok and shared the injury behind his smile.
In 2023, during a Savannah Bananas game, he was hit in the face by a baseball traveling around 90 miles per hour. The impact broke his jaw, and he has called it one of the worst pains of his life.
He needed surgery, yet returned to the field in just three weeks, wearing a protective cage on his helmet. Later, X-rays showed his teeth were at risk of dying, and the impact had shifted everything in his mouth, leaving gaps throughout.
Veneers were his way of fixing the problem before it got worse. He closed his video with a positive message about handling the curveballs life throws at you, which fits the resilience that runs through his whole story.
Jackson Olson Girlfriend: Dating Maggie Sajak
Jackson Olson’s girlfriend is Maggie Sajak, the daughter of longtime Wheel of Fortune host Pat Sajak. The couple went public on April 21, 2026, with a photo in front of Cinderella’s Castle, captioned “Applications closed.”
That caption was a callback to a viral TikTok from December 2025, where Jackson joked about accepting applications for a girlfriend after being single for years. The hard launch felt like the perfect ending to his own running joke.
Despite rumors, they did not meet at Disney. Their relationship started around baseball, and Maggie has been spotted in Bananas yellow cheering him on. They have managed long distance well, and Jackson has already met her famous dad, whom he described as a great guy.
Maggie has also shown up in the DWTS audience to support him. For a guy juggling two demanding careers, having a partner who understands public life clearly helps keep him grounded.
Their Shared Love for Disney
Disney is a big part of their story. The couple has visited both Disney World and Disneyland, and they have even run RunDisney races together. Jackson has said he booked a Disney Cruise as cooldown time after his hectic season.
He also has a practical tip for fans who love the vibe but not the price: Disney Springs is a free alternative to buying a park ticket. His must-try snack there is the cheeseburger spring rolls, a recommendation he clearly takes seriously.
Jackson Olson Net Worth and Income Sources
Jackson Olson’s net worth has not been publicly confirmed, and online figures vary so wildly that most are unreliable. Many sites even confuse him with other people sharing his name, so treat any exact number with caution.
What is clear is how he earns. His income comes from his role with the Savannah Bananas, brand partnerships, and sponsored content across a combined audience of more than three million followers. DWTS adds a national TV paycheck and a big jump in visibility.
From an industry angle, his real asset is his audience. Creator-athletes like Jackson earn through attention as much as performance, and every viral moment, good or bad, feeds future deals. If his DWTS run continues, his earning power will likely grow well beyond baseball.
Self-Care, Recovery and Staying Off Social Media
Balancing baseball and ballroom takes a toll, so Jackson keeps a steady recovery routine. He relies on electrolytes, tart cherry juice, a Theragun, and massages to keep his muscles ready for both rehearsal and game days.
His downtime is refreshingly normal. He starts with morning coffee, unwinds at night with TV or his Nintendo Switch, and openly admits to some “bed rotting” when he gets the chance. When he wants a favorite treat, he usually orders Chipotle.
Interestingly, he has been limiting his time online during the show. After the Guillermo backlash, he chose to stay off social media to protect his peace. He has said he does not want online opinions to shape how he sees himself, which is a mature choice for someone whose career started there.
Plans After DWTS
Once his DWTS run ends, Jackson plans to take about two months off to decompress. After nonstop travel and rehearsals, he wants real rest before the next Bananas season begins.
He has no plans to leave baseball. He wants to keep playing for the Savannah Bananas as long as possible, since the team gave him the platform that changed his life.
Still, he is open to new opportunities in TV, including hosting and acting. With his on-camera comfort and growing mainstream fanbase, that next chapter seems less like a dream and more like a natural step.
FAQs
What position does Jackson Olson play for the Savannah Bananas?
Jackson Olson plays infield for the Savannah Bananas and wears jersey No. 8. He has mainly played second and third base. He bats left-handed and throws right-handed.
Who is Jackson Olson’s DWTS partner?
His partner on Dancing with the Stars Season 35 is pro dancer Emma Slater. Together they have performed styles including the waltz and quickstep, earning steady praise from the judges for his improvement.
Is Jackson Olson still on Dancing with the Stars?
Yes, Jackson Olson remained in the competition after Week 6, Dedication Night, with a score of 32 out of 40. He is among the remaining couples heading into the next themed weeks of the season.
Was Jackson Olson ever drafted into MLB?
No, he was not. He drew interest after playing in the Cape Cod League, but the shortened 2020 MLB draft left him unpicked. That setback eventually led him to content creation and the Savannah Bananas.
Where does Jackson Olson live?
Jackson Olson lives in Savannah, Georgia, home base of the Savannah Bananas. He frequently travels across the country with the team’s national tour and to LA for DWTS.
How old was Jackson Olson when he joined the Savannah Bananas?
Jackson Olson joined the Savannah Bananas in 2022 at 24 years old. He originally expected to play only six games, but his popularity kept him on the roster for every season since.
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