Jackson Olson

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, a barnstorming exhibition baseball team. Olson had over 1.5 million followers on TikTok and 409,000 on Instagram as of 2023.

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, earned America East Commissioner's Honor Roll accolades, and was named the 2020 America East Baseball Scholar-Athlete of the Year. He graduated in 2020 with a Bachelor of Science in Business Administration.

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