Jackson Olson Biography: Age, Height, Career, Videos, Girlfriend, Net Worth

Jackson Olson is an American baseball player, entertainer, and social media creator best known for his role with the Savannah Bananas and his highly successful baseball-focused TikTok content.

Olson joined the Savannah Bananas in 2022 and became one of the team’s most recognizable players. Known by the nickname “The Greatest Showman,” he combines baseball ability with dancing, comedy, crowd interaction and elaborate entertainment during games.

Early Life and Education

Jackson Daniel Olson was born on October 6, 1997, and raised in New Milford, Connecticut, under the guidance of his parents. He developed a passion for baseball while growing up and dreamed of eventually playing Major League Baseball.

At New Milford High School, Olson was a three-sport athlete who played baseball, football and basketball. Baseball became his strongest pursuit, and during his senior season he batted .464 with 23 RBIs and 14 extra-base hits. His team reached the 2016 conference championship game and the Class LL state semifinals.

Olson continued his baseball career at the University of Hartford, where he played Division I baseball for the Hartford Hawks. He appeared in 161 games for the program and was part of the 2018 America East championship team.

His college career was also notable academically. Olson graduated from the University of Hartford magna cum laude and was recognized as the 2020 America East Baseball Scholar-Athlete. He was also named to the America East All-Academic Team twice and the conference’s Commissioner’s Honour Roll three times.

After Hartford, Olson spent a graduate season at Stetson University. He also played in the prestigious Cape Cod Baseball League, where his performances attracted the attention of professional scouts.

Career

Jackson Olson began posting baseball-related content on TikTok while he was still a college baseball player. His videos combined baseball knowledge with humour and personality, helping him build an audience before he had established himself professionally in entertainment. He continued creating content during the COVID-19 pandemic, when his humorous baseball videos began reaching much larger audiences.

One of his early viral videos about playing baseball in cold weather reached around 100,000 views, showing him that his social-media content could become more than a hobby. His audience continued to grow as he posted about baseball, college life, sports experiences and everyday situations.

After graduating from college, Olson worked for Instacart while continuing to develop his social-media career. His online presence eventually attracted Major League Baseball, which brought him on as an MLB content creator. Through the partnership, he visited MLB stadiums and produced social-media content around professional baseball. He later worked with Gametime and travelled to numerous MLB stadiums while creating sports content.

His social-media success eventually changed the direction of his baseball career. In 2022, Olson made a TikTok about the Savannah Bananas, the entertainment-focused baseball organization founded by Jesse Cole. The video caught Cole’s attention, and Cole contacted Olson about creating content with the team.

Olson initially expected the opportunity to involve making a few TikTok videos. He then contacted Cole about his baseball skills and shared his experience playing college baseball and in the Cape Cod Baseball League. Two weeks later, he received an offer to play for the Savannah Bananas.

Olson joined the team in 2022 and quickly became one of its most recognizable performers. He originally played third base before becoming an infielder and later establishing himself as a regular second baseman. His Banana Ball performances combine baseball with entertainment, including dance routines, trick plays, crowd interaction and comedic moments.

The Savannah Bananas gave Olson the platform to combine his two biggest strengths: baseball and social-media entertainment. He became known as “The Greatest Showman,” a nickname that reflects his theatrical approach to Banana Ball.

His popularity continued to increase as the Bananas expanded their tours to major stadiums across the United States. Olson has played at venues including Fenway Park and other major MLB stadiums while continuing to create content around the team’s games and travels.

By 2025, Olson had become one of the most followed Savannah Bananas players on social media, with more than two million TikTok followers and hundreds of thousands of Instagram followers. His content has covered baseball, food, family, relationships, travel and his experiences performing with the Bananas.

Olson has also worked with major brands during his creator career. His partnerships have included MLB, Instacart, Gametime, Reebok and Gatorade. His Gatorade partnership was renewed for 2025, adding another major commercial relationship to his growing sports and entertainment career.

In 2026, Olson expanded his entertainment career again when he was announced as a contestant on Season 35 of Dancing with the Stars. The casting gave him an opportunity to move from performing in baseball stadiums to competing on one of American television’s best-known dance programs.

Olson’s Dancing with the Stars appearance also brought him into professional contact with contestants and personalities including Robert Irwin, Scott Hoying, Alix Earle, Hilaria Baldwin, Dylan Sprouse, Whitney Leavitt, Corey Feldman and Guillermo Rodriguez.

Personal Life

Jackson Olson has spoken publicly about his family, relationships, and journey from a shy child to an entertainer in front of large crowds. His public persona closely reflects his philosophy of embracing individuality, captured in his “Don’t Be Afraid 2 B U” motto.

Olson is the son of parents who have supported his baseball career. His father worked for Rawlings and was involved with Gold Glove presentations, giving Olson an early connection to professional baseball.

In April 2026, Olson publicly confirmed his relationship with singer and television personality Maggie Sajak. Sajak is the daughter of longtime Wheel of Fortune host Pat Sajak and has also worked as the show’s social correspondent.

Olson and Maggie Sajak have appeared together publicly and shared moments from their relationship on social media, including trips and visits connected to Olson’s baseball career. Sajak has also supported Olson during his Dancing with the Stars journey.

Social Media Handles

• TikTok: @jacksonolson_
• Instagram: @jacksonolson_
• X: @JacksonOlson_

Jackson Olson’s Net Worth

Jackson Olson’s exact net worth is estimated at around $5 million.

His income comes from several areas of his career, including his work as a Savannah Bananas player and entertainer, social-media content, brand partnerships and television appearances.

His commercial partnerships have included major companies such as Gatorade, Reebok, MLB, Instacart and Gametime. His large social-media audience and growing entertainment career have also created additional opportunities.

About the Author

Chriz Joe

Administrator

Visit Website View All Posts