Jackson Daniel Olson (born October 6, 1997) is an American baseball player, entertainer, and social media personality. He is best known as a second baseman for the Savannah Bananas, an exhibition baseball team.
Early life and education Olson was born and raised in New Milford, Connecticut, where he attended New Milford High School. He was a three-sport athlete, participating in baseball, football, and basketball. As a senior, he batted .464 with 23 RBIs and 14 extra-base hits, leading his team to the 2016 conference championship game and the Class LL state semifinals. He earned First Team Class LL All-State honors and was named to the Connecticut Hearst Media Super 15 All-Star team.
Olson began his collegiate baseball career at the University of Hartford, where he played for four seasons. During his tenure, he appeared in 161 games, posting a .288 career batting average. He was a key contributor to the 2018 team that captured the America East Championship for the first time in program history. Academically, Olson was a three-time America East All-Academic Team member. He was included among America East Commissioner's Honor Roll accolades, and won the America East Baseball Scholar-Athlete of the Year in 2020. He graduated the University of Hartford, with a Bachelor of Science in Business Administration (BSBA) in 2020.
After completing his undergraduate studies, Olson pursued a master of business administration at Stetson University, where he also played for the Hatters baseball team during the 2021 season.
Career Savannah Bananas In 2022, Olson joined the Savannah Bananas. Olson has been featured in various media outlets highlighting "Banana Ball", which combines traditional baseball with entertainment elements like choreographed dances and fan interaction.
Dancing with the Stars On May 12, 2026, Olson was announced to be joining the Dancing with the Stars cast for season thirty-five.
Personal life Olson resides in Savannah, Georgia. In April 2026, he announced on his Instagram account that he was dating Maggie Sajak.
Filmography Television
+As himself Year Title Notes 2026 Season 35; Contestant
References
External links Jackson Olson college stats at Baseball-Reference