Jackson Olson

Olson is the son of Dan and Laura Olson. He has a brother named Alex and a sister named Ari. His father played college basketball at the University of Wisconsin-Oshkosh.

Olson began dating country singer Maggie Sajak in April 2026. He has also spoken about valuing time with his family in Connecticut, including visits with his niece Hannah and his sister's children.

Olson attended New Milford High School, where he played baseball, football, and basketball. As a senior, he batted .464 with 23 RBIs and 14 extra-base hits, helping lead New Milford to the 2016 conference championship game and the Class LL state semifinals. He earned First Team Class LL All-State honors and was selected for the Connecticut Hearst Media Super 15 All-Star team.

He played four seasons at the University of Hartford, appearing in 161 games and compiling a .288 career batting average. In 2018, he helped Hartford win the first conference tournament championship in program history and earned a place on the America East All-Tournament team after batting .636 during the tournament. In 2019, he led Hartford with a .306 batting average and recorded 68 hits.

Olson was a three-time America East academic all-conference selection and was named the conference's Baseball Scholar-Athlete of the Year in 2020. He graduated from Hartford with a Bachelor of Science in Business Administration before pursuing an MBA in marketing at Stetson University, where he played for the Hatters during the 2021 season.

Olson posted his first TikTok in January 2020, a video featuring the bat challenge. His comedic coming-of-age skits focus on teenage experiences, early adulthood, and baseball. His content has included references to The Sandlot, Taylor Swift, The Greatest Showman, Disney, and food.

He has worked with Major League Baseball, Taco Bell, and Fox, and has created content at baseball stadiums around the United States. During a game against the University of Alabama, he hit a 390-foot home run after someone in the crowd told him to “stick to TikTok.”

Olson joined the Savannah Bananas in 2022 as an infielder. He initially expected to play only six games during the team's summer series, but returned for subsequent seasons. He wears No. 8 and has become one of the team's recognizable performers.

The Savannah Bananas play Banana Ball, an entertainment-focused version of baseball that incorporates choreographed dances, tricks, fan interaction, and other unusual on-field elements. Olson has said that his college videos in a Greatest Showman costume, which were unusual among college baseball players, fit the team's emphasis on entertainment.