Jackson Olson is an American baseball player, social media creator, and entertainer who has built a career by combining sports, comedy, and digital content. He is best known for playing second base with the Savannah Bananas and for creating relatable baseball and lifestyle videos on social media. In 2026, his profile grew further after he joined the cast of Season 35 of Dancing with the Stars.
From his early days as a multi-sport athlete in Connecticut to college baseball, viral TikTok content, and professional entertainment baseball, Olson has followed an unusual career path. His story shows how social media became an important part of his professional life alongside baseball.
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. He became widely known through his baseball-related social media content and later gained recognition as a player for the Savannah Bananas.
Olson’s career is different from that of a traditional professional baseball player. Instead of focusing only on competition, he has combined baseball with comedy, entertainment, fan interaction, and online storytelling. The Savannah Bananas’ entertainment-focused style has provided a platform where his personality and athletic skills can both be part of his work.
In 2026, Olson also became a contestant on Season 35 of Dancing with the Stars, adding television and ballroom dancing to his growing career.
Jackson Olson Biography
Jackson Olson was born and raised in New Milford, Connecticut. During high school, he participated in baseball, football, and basketball, showing an early interest in athletics.
At New Milford High School, Olson established himself as a talented baseball player. As a senior, he reportedly hit .464 with 23 RBIs and 14 extra-base hits and earned First Team Class LL All-State honors.
After high school, Olson continued his baseball career at the University of Hartford. He later played at Stetson University, using an additional season of NCAA eligibility. His college career gave him both athletic and academic experience.
Olson’s path toward entertainment and social media became more noticeable during and after college. He began creating videos that combined baseball with humor and everyday experiences. His content gradually attracted a large online audience.
Jackson Olson Age
His hometown is New Milford, Connecticut, where he grew up and developed his early interest in sports.
Jackson Olson Education
Olson attended New Milford High School before continuing his education at the University of Hartford.
At Hartford, he played Division I baseball and studied business administration. He was also recognized academically, including being named the America East Baseball Scholar-Athlete of the Year in 2020.
He later attended Stetson University and played baseball for the Hatters during the 2021 season. His college experience combined competitive baseball with his academic interests in business.
Jackson Olson Baseball Career
Baseball has remained one of the central parts of Jackson Olson’s career.
During college, he played several infield positions, including shortstop, third base, and second base. Baseball-Reference lists him at 6 feet 2 inches and 200 pounds, with left-handed batting and right-handed throwing.
After college, Olson’s professional baseball path did not follow the traditional Major League Baseball route. Instead, his growing social media presence opened another door.
He eventually joined the Savannah Bananas, an entertainment-focused baseball organization known for Banana Ball. Olson became one of the team’s recognizable players, combining baseball ability with dancing, comedy, and interaction with fans.
He joined the Savannah Bananas in 2022 and has played second base for the team.
Jackson Olson and Social Media
Social media played a major role in changing Olson’s career.
He began posting TikTok videos in January 2020, initially creating content around baseball and everyday experiences. His videos eventually attracted a large following, and his online presence became an important part of his professional identity.
Olson has explained that content creation gave him a way to express his personality. In a LinkedIn post, he described himself as an introverted child and said social media gave him an outlet to showcase his personality.
His content has included baseball videos, comedy, relatable experiences, family-related moments, food, relationships, and behind-the-scenes aspects of his life.
His growing audience also led to opportunities with major brands and baseball organizations. Sources have reported partnerships and work involving MLB and other well-known brands.
Jackson Olson and the Savannah Bananas
The Savannah Bananas became an important turning point in Olson’s career.
The team is known for Banana Ball, an entertainment-driven version of baseball that includes choreographed celebrations, fan interaction, and other performance elements. Olson’s combination of athletic ability and social media experience fits naturally into that environment.
His time with the Bananas has allowed him to perform for large audiences while continuing to create online content. His role is not limited to playing baseball; entertainment is also an important part of the experience.
Olson has spoken about how joining the Bananas helped him discover a passion for entertaining. In an interview surrounding his Dancing with the Stars appearance, he described himself as someone who had once been shy and had not expected to become an entertainer.
Jackson Olson on Dancing with the Stars
In May 2026, ABC announced Jackson Olson as a celebrity contestant for Season 35 of Dancing with the Stars. The announcement represented another major step in his entertainment career.
Olson’s experience with the Savannah Bananas already included dancing and performance, but Dancing with the Stars introduced him to a different form of dance and television competition.
His participation also reflects how his career has expanded beyond traditional baseball. He has moved from college athletics into entertainment baseball, social media, and television.
Jackson Olson Family
Jackson Olson was born and raised in New Milford, Connecticut. Public profiles indicate that he has a brother and a sister. His family has also appeared in some of his social media content.
His parents have been mentioned in reporting about his baseball and social media journey. People reported that his father, Dan, supported his baseball development, while his mother, Laura, has also spoken about her pride in his career.
Olson has frequently incorporated family relationships and personal experiences into his online storytelling, which has contributed to the personal style of his content.
Jackson Olson Personal Life
Jackson Olson’s personal life has received increased attention because of his relationship with Maggie Sajak, the daughter of longtime Wheel of Fortune host Pat Sajak.
Reports in April 2026 identified Olson and Maggie Sajak as a couple. Olson later publicly acknowledged the relationship through social media.
Beyond his relationship, Olson often shares aspects of everyday life, family, baseball, food, humor, and personal experiences through his social media accounts.
Jackson Olson Social Media
Social media remains a major part of Jackson Olson’s public career.
His content has attracted millions of followers across platforms, particularly TikTok and Instagram. His videos frequently combine baseball, humor, relationships, and relatable moments from everyday life.
His social media success also helped him attract attention from baseball organizations and brands. MLB selected him for its Creator Class in 2021, according to reporting on his early content career.
Fans can find his public content by searching for his verified or official social media accounts under the name Jackson Olson.
Jackson Olson Net Worth
Jackson Olson’s exact net worth is not publicly verified.
Online sources may publish different estimates, but there is no reliable public financial record that confirms a specific figure. His potential sources of income can include baseball-related work, social media partnerships, brand collaborations, entertainment appearances, and other professional opportunities.
Because these earnings can change over time and private contracts are generally not publicly disclosed, specific net-worth numbers should be treated as estimates rather than confirmed facts.
Jackson Olson Career Highlights
Some notable points in Jackson Olson’s career include:
- Playing Division I college baseball at the University of Hartford.
- Continuing his college baseball career at Stetson University.
- Being recognized as an America East Baseball Scholar-Athlete of the Year.
- Building a large audience through TikTok and other social platforms.
- Becoming part of MLB’s Creator Class.
- Joining the Savannah Bananas in 2022.
- Building a career that combines baseball and entertainment.
- Joining the cast of Season 35 of Dancing with the Stars in 2026.
Interesting Facts About Jackson Olson
Here are some interesting facts about Jackson Olson:
- He was a multi-sport athlete.
In high school, Olson played baseball, football, and basketball. - He began making TikTok videos in 2020.
His first TikTok was posted in January 2020. - Social media changed his career path.
His videos attracted a significant audience and eventually created professional opportunities outside traditional baseball. - He became a Savannah Banana.
Olson joined the Savannah Bananas in 2022 and became known for combining baseball with entertainment. - He joined Dancing with the Stars.
In 2026, Olson expanded his entertainment career by joining Season 35 of the popular dance competition. - He has worked with baseball-related brands and organizations.
His social media career has included collaborations connected with MLB and other commercial partners.
Frequently Asked Questions About Jackson Olson
Who is Jackson Olson?
Jackson Olson is an American baseball player, social media creator, and entertainer. He is known for playing with the Savannah Bananas and for his baseball and lifestyle content online.
How old is Jackson Olson?
Jackson Olson was born on October 6, 1997. He is 28 years old as of September 2026.
Where is Jackson Olson from?
Jackson Olson is from New Milford, Connecticut, United States.
What does Jackson Olson do?
He is a baseball player, entertainer, and social media personality. He plays for the Savannah Bananas and creates content for his online audience.
What is Jackson Olson known for?
He is known for his work with the Savannah Bananas, his viral social media content, and his appearances as a contestant on Season 35 of Dancing with the Stars.
Is Jackson Olson married?
Public reporting in 2026 identifies Jackson Olson as being in a relationship with Maggie Sajak. There is no indication from the cited sources that they are married.
What is Jackson Olson’s net worth?
Jackson Olson’s exact net worth has not been reliably confirmed through public financial records. Online estimates should therefore be treated cautiously.
Official LinkedIn Perfile : https://www.linkedin.com/in/jackson-olson-2a480b116
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Conclusion
Jackson Olson has built a distinctive career by bringing together baseball, social media, and entertainment. His journey began with competitive sports in Connecticut and continued through college baseball before his online content opened new professional opportunities.
His work with the Savannah Bananas helped establish him as both an athlete and entertainer, while his large social media presence expanded his reach beyond the baseball field. In 2026, joining Dancing with the Stars marked another major chapter in his public career.
Today, Jackson Olson is recognized not only as a baseball player but also as a content creator and entertainer whose career continues to develop across sports, social media, and television.