If you have been wondering who is Jackson Olson, he is a Connecticut-born baseball player, social media creator and entertainer who has become one of the most recognizable personalities associated with the Savannah Bananas. His career has taken an unusual route, moving from college baseball to viral online content, exhibition baseball, live entertainment and, in 2026, a national television appearance on Dancing with the Stars.
Olson has built an audience by showing that baseball can be more than a traditional nine-inning game. His work with the Savannah Bananas combines athletic performance with dance, comedy, music and fan interaction, while his social-media accounts give viewers a look at his personality away from the field. That combination has helped him develop a following far beyond traditional baseball audiences.
Jackson Olson’s Early Life and Hometown
Jackson Olson was born on October 6, 1997, in New Milford, Connecticut. He grew up in the town and developed a strong connection with baseball at an early age.
His childhood interest in the sport eventually developed into a serious playing career. Olson attended New Milford High School before continuing his education and baseball career at the University of Hartford.
Although he is now known for his energetic personality and willingness to perform in front of thousands of people, Olson has described himself as considerably more reserved when he was younger. His later transformation into a highly visible entertainer is one of the more distinctive aspects of his story.
Baseball provided the foundation, but social media and entertainment eventually gave him another way to express himself.
Jackson Olson’s College Baseball Career
Olson played Division I baseball at the University of Hartford. He spent four seasons with the Hartford baseball program, appearing in 161 games and making 146 starts.
He primarily played in the infield and became part of an important period in the program’s history. In 2018, Hartford won its first America East Championship and advanced to the NCAA Tournament for the first time.
Olson’s individual production also made him a valuable member of the team. During his Hartford career, he recorded 161 hits and finished with a .287 batting average, according to the university’s athletic records.
His junior season in 2019 was particularly productive. He hit .306 and recorded 68 hits, while also contributing runs and RBIs.
His accomplishments were not limited to baseball. Olson was a marketing major and received academic recognition during his college career. In 2020, he was named the America East Baseball Scholar-Athlete.
After completing his time at Hartford, Olson continued playing college baseball at Stetson University in 2021.
The Turning Point in His Career
Olson’s career could have followed a conventional path for a college baseball player, but social media changed his direction.
Rather than treating online platforms as simply a place to share occasional baseball clips, Olson began using them to tell stories and create entertaining videos. His content gradually attracted a much larger audience.
The approach was different from conventional sports content. Instead of focusing exclusively on statistics, game results and training, Olson incorporated humor, personal experiences, relationships, food, travel and everyday situations.
That broader style made his videos accessible to people who were not necessarily dedicated baseball fans.
The combination of baseball ability and entertainment skills eventually caught the attention of the Savannah Bananas.
How Jackson Olson Joined the Savannah Bananas
Olson’s connection with the Savannah Bananas began through social media.
In 2022, he created a TikTok video that helped bring him to the attention of the organization. The opportunity eventually led to him joining the Savannah Bananas, where he found an environment that allowed him to combine competitive baseball with performance.
The Savannah Bananas are known for Banana Ball, a fast-moving form of baseball built around entertainment and audience participation. Players are expected to contribute to the atmosphere as well as perform on the field.
For Olson, the format provided an opportunity to use skills that were not always visible during his traditional college baseball career.
He could play the infield while also dancing, interacting with fans and participating in the theatrical elements that have helped the Bananas become a social-media phenomenon.
What Position Does Jackson Olson Play?
Olson is an infielder and has become particularly associated with second base during his time with the Savannah Bananas.
His baseball background makes the transition into the Bananas natural because he already had years of competitive experience before joining the organization.
What distinguishes his role, however, is what happens around the actual baseball plays.
A Bananas game can involve music, choreography, celebrations and comedic routines. Players are encouraged to be personalities rather than simply athletes.
Olson has embraced that concept more visibly than many traditional baseball players, which has helped him become one of the team’s most recognizable faces.
Why Is Jackson Olson So Popular on Social Media?
Olson’s popularity is closely connected to his ability to turn ordinary experiences into short-form entertainment.
His videos frequently combine baseball with humor and storytelling. He also shares personal moments and behind-the-scenes content from his life as a Savannah Bananas player.
His social-media following grew into the millions, with his TikTok account becoming one of the most important platforms in his career.
The appeal is partly his personality. Olson is energetic, expressive and comfortable performing for a camera. He also has a distinctive appearance, including the spiky, frosted hairstyle that has become closely associated with his public image.
His content demonstrates how sports personalities can build audiences independently of traditional television or newspaper coverage.
Jackson Olson and the Savannah Bananas Entertainment Style
The Savannah Bananas have built their identity around making baseball entertaining for a broad audience, and Olson fits naturally into that environment.
Players are encouraged to dance, celebrate, interact with spectators and participate in routines that would be unusual during a traditional professional baseball game.
Olson has become particularly known for his dancing and theatrical performances.
That background became especially important in 2026 when he made the transition from the baseball field to a national dance competition.
The skills he developed while performing for Bananas fans gave him experience working with large crowds, cameras and choreographed routines.
Jackson Olson Joins Dancing With the Stars
One of the biggest developments in Olson’s career came in May 2026 when ABC announced that he would compete on Season 35 of Dancing with the Stars.
The casting was a natural extension of his entertainment career, even though ballroom dancing represented a very different challenge from baseball.
Olson was paired with professional dancer Emma Slater.
The opportunity also had an interesting backstory. Before being officially selected for the show, Olson had posted social-media content joking about appearing on Dancing with the Stars. What began as an online joke eventually became reality.
Olson later explained that he never expected his childhood self to end up in this position. He has spoken publicly about being shy when he was younger and discovering his passion for entertainment later in life.
Jackson Olson’s Dancing With the Stars Debut
Olson made his Dancing with the Stars debut during the show’s Season 35 premiere in September 2026.
He and Emma Slater opened the men’s portion of the two-night premiere with a cha-cha performed to the Spice Girls’ “Wannabe.” The first-week theme centered on songs that were No. 1 during the celebrities’ birth years.
The performance earned 15 points out of 30 from the judges.
While the score reflected areas where Olson needed to improve, the performance also generated a strong audience response. The judges noted his entertainment ability while pointing out that his movements needed more refinement.
The experience represents a major new stage in Olson’s career because he is now being evaluated not only as a baseball entertainer but also as a ballroom performer.
Who Is Jackson Olson Dating?
Olson is in a relationship with Maggie Sajak, the daughter of longtime Wheel of Fortune host Pat Sajak.
The couple publicly confirmed their relationship in April 2026 after sharing a photograph together at Walt Disney World.
Their relationship quickly became a topic of interest among fans because both Olson and Sajak have established public profiles.
Sajak works with Wheel of Fortune as its social correspondent and has also pursued a legal career. She has publicly supported Olson during his Dancing with the Stars experience.
The couple has shared moments from their relationship on social media, including trips and appearances connected with Olson’s life and career.
Reports about their relationship have also stated that they first met in person at a Los Angeles Dodgers playoff game in October 2025.
Jackson Olson’s Connection to New Milford
Despite his growing national profile, Olson has continued to maintain a visible connection with his Connecticut hometown.
His baseball roots in New Milford remain an important part of his story. In July 2026, his hometown honored him by naming a Little League field after him.
The recognition was especially meaningful because Olson had spent part of his childhood developing his love for baseball at the local level.
The milestone also illustrates how far his career has progressed. The sport he began playing as a child eventually became the foundation for a career that now includes national television and millions of social-media viewers.
What Does Jackson Olson Do Outside Baseball?
Olson’s career now covers several areas rather than one conventional job title.
He remains a baseball player with the Savannah Bananas, but he is also a content creator, entertainer and television personality.
His social-media work includes baseball videos, comedy, personal storytelling and lifestyle content. His work with the Bananas adds live performance and audience interaction, while Dancing with the Stars has introduced him to ballroom dancing.
This combination is increasingly important to understanding his career.
Olson is not simply an athlete who happens to post videos online. Digital entertainment has become an important part of his professional identity.
Jackson Olson’s Influence on Young Fans
Olson has also spoken about the importance of encouraging young people to be comfortable with their interests and personalities.
His own career illustrates that a person does not necessarily have to choose one identity. He can be a baseball player while also dancing, making videos and entertaining an audience.
That message has become part of his public image.
His experience is particularly relevant for young athletes who may feel pressure to focus exclusively on competition. Olson’s career shows how athletic skills can coexist with creative interests and entertainment.
His transition from a relatively shy childhood personality to a performer in front of large crowds has become an important part of the story he tells about himself.
Why People Are Searching for Jackson Olson
Search interest surrounding Olson increased substantially as his television career developed.
Savannah Bananas fans already knew him as a popular infielder and entertainer. Social-media users recognized him for his viral videos and distinctive personality. Dancing with the Stars introduced him to viewers who may have never watched a Savannah Bananas game.
His relationship with Maggie Sajak has added another layer of public interest.
Together, these developments have transformed Olson from a college baseball player into a recognizable entertainment personality with an audience spanning sports, social media and television.
Jackson Olson’s Career Today
As of September 2026, Olson is continuing his involvement with the Savannah Bananas while competing on Season 35 of Dancing with the Stars.
His current career reflects the unusual path he has taken since college.
He did not become known solely through a traditional professional baseball organization. Instead, his visibility grew through a combination of baseball, social media, live performance and personality-driven content.
His participation in Dancing with the Stars has provided another opportunity to demonstrate the performance skills that have become a major part of his identity.
For anyone asking who is Jackson Olson, the simplest answer is that he is a baseball player who built a second career as an entertainer and digital creator, eventually turning that combination into a national television opportunity.
A Career Built Around Baseball and Entertainment
Olson’s story is notable because every stage of his career has built on the previous one.
His childhood love of baseball led to high school competition. That developed into Division I baseball at Hartford and later Stetson. Social media then created an opportunity to reach a much larger audience, while the Savannah Bananas provided a place where baseball and entertainment could exist together.
Now, Dancing with the Stars has added another dimension.
The move from a baseball infield to a ballroom floor may seem unusual, but Olson’s career has always involved more than simply playing the game. His ability to perform, create content and connect with audiences has become as important to his public identity as his athletic background.
With his Savannah Bananas career continuing and his television journey underway, Olson’s profile remains closely tied to the changing relationship between sports, social media and entertainment.
Jackson Olson’s journey from Connecticut baseball player to Savannah Bananas entertainer and national television personality continues to unfold, giving fans plenty to watch both on the field and beyond it.