Jackson Olson is an American baseball player, entertainer, and social media personality best known for playing for the Savannah Bananas.
He later built a large online following by combining baseball with comedy and relatable content.
His career took another exciting turn in 2026 when he joined the cast of Dancing with the Stars Season 35.
Who is Jackson Olson?
Jackson Olson is a baseball player and content creator who has found success both on the field and across social media.
He is particularly known for his role as an infielder with the Savannah Bananas, where traditional baseball is mixed with entertainment, dancing, and interaction with fans.
Alongside baseball, Jackson has built a strong social media career. His content focuses on baseball, relationships, family, food, and relatable moments from everyday life.
This combination of sports and entertainment has helped him reach millions of followers and become a recognizable personality beyond the baseball field.
Jackson Olson Early Life
Jackson Daniel Olson was born on October 6, 1997, in New Milford, Connecticut, and grew up there with his family.
He is the son of Dan and Laura Olson and has one brother, Alex, and one sister, Ari. His father also had a college sports background, having played basketball at the University of Wisconsin-Oshkosh.
Jackson developed a love for sports while growing up in New Milford. At New Milford High School, he competed in baseball, football, and basketball, making him a three-sport athlete.
Baseball eventually became his main focus. During his senior year, he batted .464 with 23 RBIs and 14 extra-base hits.
He also earned First Team Class LL All-State honors and other regional recognition for his performance.
Jackson Olson Age
Jackson Olson is 28 years old as of 2026. He was born on October 6, 1997, in New Milford, Connecticut. His October birthday makes him a Libra.
Jackson Olson Nationality and Ethnicity
Jackson Olson is American and was born in New Milford, Connecticut.
He grew up in the United States and later continued his education and baseball career at American universities.
Jackson Olson Education
Jackson attended New Milford High School, where he played baseball, football, and basketball.
After high school, he continued his baseball career at the University of Hartford, where he played for four seasons.
He appeared in 161 games and finished his college career with a .288 batting average. He graduated from the University of Hartford in 2020 with a bachelor’s degree in business administration.
He then attended Stetson University, where he pursued a Master of Business Administration and played baseball during the 2021 season.
College Baseball Career (2017–2021)
Jackson Olson began his competitive baseball career at the University of Hartford, where he played for four seasons.
He appeared in 161 games and finished his Hartford career with a .288 batting average, 161 hits, 30 doubles, four triples, four home runs, and 57 RBIs.
His strongest season came in 2019, when he hit .306 with 68 hits. He also earned academic recognition and was named the 2020 America East Baseball Scholar-Athlete of the Year.
After graduating from Hartford in 2020, Jackson continued his baseball career at Stetson University while pursuing an MBA.
He played for the Hatters during the 2021 season. His college years gave him valuable experience as both an athlete and a student.
At the same time, his business education later became useful as he developed his career in social media and entertainment.
Social Media Career (2020–Present)
Jackson began creating content on social media around 2020, combining his baseball experience with humor and relatable storytelling.
His videos cover baseball, relationships, family, food, and everyday experiences. His content gradually attracted a large audience, turning his social media work into an important part of his professional career.
His online success also helped him build connections within the baseball world.
Rather than leaving baseball behind after college, Jackson found a way to bring the sport into his digital content.
This eventually opened the door to opportunities with the Savannah Bananas and helped establish him as a sports entertainer.
Savannah Bananas Career (2022–Present)
Jackson joined the Savannah Bananas in 2022 as an infielder and became particularly known for playing second base.
The team has a unique approach called Banana Ball, which combines baseball with entertainment, choreographed dances, and interaction with the crowd.
Playing for the Bananas allowed Jackson to combine his baseball skills with his outgoing personality and social media experience.
He became one of the recognizable faces connected with the team while continuing to create content for his growing online audience.
Dancing with the Stars (2026)
Jackson took another major step into television in 2026 when he was announced as a contestant on Season 35 of Dancing with the Stars.
His casting was announced on May 12, 2026, adding a new entertainment opportunity to his career.
His appearance on the dance competition represents a new chapter beyond baseball and social media.
With an athletic background and years of performing for crowds with the Savannah Bananas, Jackson now has the opportunity to showcase his personality and competitive side in a completely different setting.
Jackson Olson TV Shows
Jackson Olson is set to appear as a contestant on:
- Dancing with the Stars — Season 35 (2026)
What is Jackson Olson Known For?
Jackson Olson is best known for his work with the Savannah Bananas and his successful social media career.
He has built a large audience by creating entertaining baseball content and relatable videos about everyday life.
His participation in Dancing with the Stars has also brought him to a wider television audience.
Does Jackson Olson Still Play for the Savannah Bananas?
Yes. Jackson Olson continues to be associated with the Savannah Bananas in 2026.
He joined the team in 2022 and plays as an infielder, with his role particularly associated with second base.
His role with the Bananas has become an important part of his identity as both an athlete and entertainer.
The team’s unique approach to baseball also gives Jackson plenty of opportunities to combine his athletic ability with his personality and social media skills.
Is Jackson Olson in a Relationship?
Yes. Jackson Olson is in a relationship with Maggie Sajak. The relationship was announced in April 2026 when Jackson shared it on Instagram.
Jackson Olson Girlfriend
Jackson Olson is currently in a relationship with Maggie Sajak, the daughter of longtime Wheel of Fortune host Pat Sajak.
The couple made their relationship official in April 2026 when Jackson shared a photo of them together at Disney World on Instagram.
He captioned the post “Applications closed,” referring to his earlier social-media search for a girlfriend.
Since going public, Jackson and Maggie have continued to share moments from their relationship.
They have been seen together at Disney World and at Savannah Bananas games, where Maggie has supported Jackson from the stands.
Jackson has also spoken warmly about their relationship, describing it as an important part of his life.
In June 2026, he said he believed he had found “the one,” while in August he spoke about making time for Maggie alongside his busy Dancing with the Stars schedule.
Jackson and Maggie are still together as of August 2026. They continue their relationship while he balances his Savannah Bananas career and Dancing with the Stars, with Maggie supporting his television journey.
Who Has Jackson Olson Dated?
Jackson Olson has kept his dating life relatively private, but one relationship has become publicly confirmed.
In April 2026, he made his relationship with Maggie Sajak official on Instagram.
The couple shared a photo together during a Disney trip, with Jackson captioning the post “Applications closed,” referring to his earlier social-media search for a girlfriend.
Before meeting Maggie, Jackson had spoken openly about being single for several years.
In December 2025, he posted a humorous “boyfriend application” video on TikTok, jokingly inviting people to apply for the role.
The video went viral and attracted a large response from followers. A few months later, his relationship with Maggie became public, marking his first widely reported romance.
Jackson and Maggie have continued to share moments from their relationship on social media.
In June 2026, Jackson spoke warmly about Maggie and said he had found someone who shared the values and qualities he wanted in a partner.
Their relationship has since become an important part of his personal life as he continues his career with the Savannah Bananas and prepares for Dancing with the Stars.
Jackson Olson Net Worth
Jackson Olson has an estimated net worth of $1 million as of 2026. She earns money through several areas of his career.
His work as a Savannah Bananas baseball player and entertainer is one part of his income.
He also has a substantial social media career, which creates opportunities through digital content and brand partnerships. His television work adds another professional avenue.
With his appearance on Dancing with the Stars in 2026, Jackson has expanded his career further into mainstream entertainment.
Jackson Olson Salary
Jackson Olson earns more than $100,000 annually through his work with the Savannah Bananas.
His role combines baseball and entertainment, making him part of the team’s unique Banana Ball experience.
He also earns through social media, brand partnerships, and content creation. His growing presence in entertainment, including Dancing with the Stars, provides additional career opportunities.
Jackson Olson Height and Weight
Jackson Olson is listed at 6 feet 2 inches which is equal to 188 centimeters and 1.88 meters tall and weighs approximately 195 pounds which is equal to 88 kilograms.
These measurements come from his Stetson University baseball profile, where he was listed as an infielder. His athletic build reflects his background as a competitive baseball player.
Social Media Presence
Jackson Olson built a large following through videos centered on baseball, comedy, relationships, family, food, and relatable moments.
His TikTok audience has grown into the millions, while he also maintains a presence on Instagram.
His online content has helped him connect with audiences beyond traditional baseball fans.
It has also become an important part of his identity as an entertainer, especially as he continues to combine sports with television and digital content.
Conclusion
Jackson Olson has built an unusual career that brings together baseball, social media, and entertainment.
From playing Division I baseball to joining the Savannah Bananas, he has continued to find new ways to turn his passion for sports into a career.
His growing presence on social media and his move to Dancing with the Stars have taken his career well beyond the baseball field.