Jackson Olson Bio: Age, Career,Girlfriend & Savannah Bananas
Jackson Olson has built an unusual career that combines baseball, entertainment, social media and storytelling. He first gained attention through creative baseball videos on TikTok. Later, he became a standout player for the Savannah Bananas.
Today, Olson enjoys a much larger platform than he once imagined. He has millions of social media followers and performs for huge crowds through Banana Ball. Additionally, he joined the cast of Dancing with the Stars Season 35 in 2026.
His journey stands out because he did not follow a traditional professional baseball path. Instead, he created opportunities through talent, creativity and persistence.
Who Is Jackson Olson?
Jackson Daniel Olson is an American baseball player, entertainer and social media personality. He was born on October 6, 1997, in New Milford, Connecticut.
Olson currently plays as an infielder for the Savannah Bananas. He wears jersey number 8 and has become one of the team’s most recognizable personalities.
However, baseball represents only one part of his career. Olson also creates comedy, lifestyle and sports content for millions of online followers.
His social media presence helped transform him from a college baseball player into an entertainment personality. Moreover, his story shows how digital platforms can create unexpected career opportunities.
Jackson Olson Age and Birthplace
Jackson Olson was born on October 6, 1997. Therefore, he is 28 years old in 2026.
He grew up in New Milford, Connecticut, where he developed a strong passion for baseball. His father, Dan Olson, also played an important role in his early baseball development.
Jackson’s father coached his teams during his younger years. Consequently, baseball became an important part of their relationship.
Olson later used that family connection in his social media storytelling. His videos often highlight family, friendships, relationships and personal experiences.
Jackson Olson Education
Olson attended New Milford High School in Connecticut. He became a talented three-sport athlete during his school years.
He played baseball, football and basketball. However, baseball eventually became his main sporting focus.
During his senior baseball season, Olson recorded impressive numbers. He hit .464 with 23 RBIs and 14 extra-base hits.
His performances helped New Milford reach the conference championship game. The team also reached the Class LL state semifinals.
Furthermore, Olson earned First Team Class LL All-State honors. He also received recognition from the Connecticut Hearst Media Super 15 All-Star team.
Jackson Olson College Baseball Career
After high school, Olson continued his baseball career at the University of Hartford.
He played four seasons for the Hartford Hawks. During that period, he appeared in 161 games and recorded a .288 career batting average.
One of his biggest college achievements came in 2018. Hartford won its first America East Championship that year.
The victory gave Olson an opportunity to compete in the NCAA Division I tournament. It also strengthened his reputation as a talented college player.
Academically, Olson also performed well. He earned America East All-Academic Team recognition three times.
He also received America East Commissioner’s Honor Roll recognition. Additionally, he became the 2020 America East Baseball Scholar-Athlete of the Year.
Olson graduated from Hartford in 2020 with a Bachelor of Science in Business Administration.
Jackson Olson and the Arizona Diamondbacks
Professional baseball once appeared to be Olson’s next destination.
While playing in the Cape Cod League, Olson attracted attention from professional scouts. The Arizona Diamondbacks eventually offered him an opportunity.
However, Olson decided to continue his education instead of immediately pursuing professional baseball.
He later transferred to Stetson University. There, he played baseball during the 2021 season.
The COVID-19 pandemic also changed the baseball landscape during this period. Changes to eligibility rules gave Olson another opportunity to continue playing.
His decision eventually helped shape the unconventional career that followed.
How Jackson Olson Joined the Savannah Bananas
Olson’s path to the Savannah Bananas began through social media.
During college, he started creating humorous baseball videos. He continued posting during the COVID-19 pandemic and gradually built an audience.
One of his biggest inspirations involved combining baseball with entertainment. He also created content connected to musicals, food and baseball culture.
At one point, Olson took an MLB stadium tour. During that trip, he discovered the Savannah Bananas on TikTok.
He then created a TikTok aimed at getting owner Jesse Cole’s attention. Remarkably, the strategy worked.
Cole eventually contacted Olson and invited him to play several games. Olson joined the Bananas in 2022.
What started as a short opportunity became a major career breakthrough.
Jackson Olson and Banana Ball
The Savannah Bananas operate around an entertainment-focused version of baseball called Banana Ball.
The games combine baseball with music, choreography, comedy and direct fan interaction. Therefore, players need athletic ability and entertainment skills.
Olson became particularly successful in this environment.
He performs dances, participates in trick plays and interacts with fans. His personality also fits the team’s creative approach.
Disney+ has described Olson as the team’s number eight infielder. The platform also highlights his social media presence and unique personality.
Olson once described himself as a shy person who rarely performed publicly. However, Banana Ball helped him discover a different side of himself.
Jackson Olson Social Media Career
Social media played a major role in Olson’s transformation.
His TikTok account @jacksonolson_ attracted millions of followers. His Instagram audience also grew rapidly.
His content covers much more than baseball. He frequently shares food, relationships, family moments, travel and entertainment.
He also creates baseball rankings and behind-the-scenes videos. As a result, his content reaches both sports fans and general audiences.
Sports Illustrated reported that Olson had more than two million TikTok followers and about 895,000 Instagram followers in 2025.
His online success also helped him become a recognizable figure beyond Banana Ball.
Jackson Olson’s Content Style
Olson’s content succeeds because he combines sports with relatable storytelling.
He often uses humor instead of presenting himself as a traditional sports celebrity. Consequently, viewers can connect with his personality away from the baseball field.
His videos also highlight his relationships with family and teammates.
His father, Dan, remains an important part of his story. Jackson has shared emotional moments involving their baseball relationship.
In 2025, the pair played catch at Fenway Park during the Savannah Bananas’ national tour. The moment represented a memorable full-circle experience for father and son.
Jackson Olson Girlfriend: Maggie Sajak
Jackson Olson’s personal life also attracted significant attention in 2026.
He is dating Maggie Sajak, the daughter of longtime Wheel of Fortune host Pat Sajak.
The couple made their relationship Instagram official in April 2026. They shared a photo from Disney’s Magic Kingdom, where they appeared together.
Their relationship quickly became a popular topic among entertainment and sports fans.
Olson later described Sajak as someone who shares his values and personality. He also expressed strong feelings about their relationship in a June 2026 post.
By June, Olson said he believed he had found “the one.”
The couple has continued sharing moments together while managing their busy careers.
Jackson Olson on Dancing with the Stars
In 2026, Olson reached another major career milestone.
ABC announced him as a contestant for Season 35 of Dancing with the Stars. His casting followed several social media posts where he expressed interest in joining the program.
The full Season 35 cast was officially revealed on September 2, 2026. Olson will compete alongside professional dancer Emma Slater.
The partnership creates an interesting challenge for Olson. Although he performs regularly with the Savannah Bananas, ballroom dancing requires different techniques.
Still, his entertainment background could give him an advantage.
Olson has already developed strong performance skills through Banana Ball. Therefore, fans will watch closely to see how those skills translate to ballroom competition.
Dancing with the Stars Season 35 premieres on September 15, 2026.
Jackson Olson and His Dancing Background
Dancing became an unexpected part of Olson’s baseball career.
Before joining the Savannah Bananas, he did not consider himself a natural performer. In fact, he once described himself as someone who stayed in the background.
That changed after joining the Bananas.
The team encouraged players to dance, perform and express themselves during games. Olson embraced the opportunity and developed his own performance style.
He even earned the nickname “The Greatest Showman” because of routines inspired by the musical film.
His love for musical theater has therefore become part of his baseball identity.
Jackson Olson Personality and Philosophy
Olson often promotes the message “Don’t Be Afraid 2 B U.”
That message reflects his personal transformation.
He grew from a quiet college athlete into a confident performer with a large online following. Instead of hiding his personality, he learned to use it.
His content also encourages people to enjoy life and maintain meaningful relationships.
Moreover, Olson often discusses the importance of family and authenticity.
His career demonstrates that success does not always follow a straight path. Sometimes, unexpected opportunities can produce better results than carefully planned careers.
Jackson Olson Career Highlights
Jackson Olson’s career includes several important milestones.
Key highlights include:
- Growing up as a three-sport athlete in Connecticut.
- Reaching the Class LL state semifinals with New Milford.
- Winning the 2018 America East Championship with Hartford.
- Earning America East Scholar-Athlete recognition.
- Receiving an opportunity from the Arizona Diamondbacks.
- Playing college baseball at Stetson University.
- Building a large following through social media.
- Joining the Savannah Bananas in 2022.
- Becoming a leading Banana Ball personality.
- Performing at major baseball stadiums across the United States.
- Reaching millions of followers on TikTok.
- Joining Dancing with the Stars Season 35 in 2026.
What Is Jackson Olson Known For?
Jackson Olson is best known for his role with the Savannah Bananas.
However, his popularity extends far beyond baseball.
He is also known for his TikTok videos, humorous baseball content and entertainment performances. Additionally, his relationship with Maggie Sajak has increased public interest in his personal life.
Now, his appearance on Dancing with the Stars represents another major chapter.
His growing career shows how sports and social media can work together. It also demonstrates how athletes can build personal brands outside traditional competition.
Jackson Olson’s Net Worth
Jackson Olson’s exact net worth remains undisclosed.
Therefore, online estimates should receive caution because they lack confirmed financial records.
His income likely comes from multiple professional activities. These may include baseball, social media partnerships, appearances and brand collaborations.
His growing audience also gives him valuable opportunities in digital entertainment.
However, there is no reliable public figure that confirms his current total wealth.
Frequently Asked Questions About Jackson Olson
How old is Jackson Olson?
Jackson Olson is 28 years old in 2026. He was born on October 6, 1997.
Where is Jackson Olson from?
Jackson Olson comes from New Milford, Connecticut, United States.
What does Jackson Olson do?
Jackson Olson is a baseball player, entertainer and social media personality.
What team does Jackson Olson play for?
Olson plays for the Savannah Bananas as an infielder.
When did Jackson Olson join the Savannah Bananas?
Olson joined the Savannah Bananas in 2022.
Is Jackson Olson on Dancing with the Stars?
Yes. Jackson Olson competes on Dancing with the Stars Season 35 in 2026.
He partners with professional dancer Emma Slater.
Who is Jackson Olson’s girlfriend?
Jackson Olson is dating Maggie Sajak, the daughter of Pat Sajak. The couple made their relationship public in April 2026.
What is Jackson Olson famous for?
Jackson Olson is famous for Savannah Bananas baseball, Banana Ball, TikTok content and entertainment performances.
Final Thoughts on Jackson Olson
Jackson Olson’s biography represents a story of reinvention, persistence and creativity.
He began as a talented baseball player from Connecticut. However, his career eventually moved beyond traditional baseball.
Social media helped him find a new audience. Then, the Savannah Bananas gave him a platform to combine baseball and entertainment.
Now, Dancing with the Stars offers another opportunity to expand his career.
His story also carries a simple lesson. You do not always need to follow the expected path to build a successful career.
Olson followed his interests, embraced his personality and created opportunities through social media.
As a result, the former college baseball player has become a recognizable sports and entertainment personality.
His next chapter on Dancing with the Stars could introduce him to an even wider audience.
