Jackson Olson Wiki, Age, Height, Net Worth 2026

Jackson Olson is an American baseball player, entertainer and social media personality who has become one of the faces of the Savannah Bananas, the exhibition baseball team behind the high-energy Banana Ball format. Since joining the Bananas in 2022, the New Milford, Connecticut native has fused competitive infield play with choreographed on-field dance routines that turned him into a TikTok star with over a million followers. In 2026 his profile crossed into mainstream television twice over: first through his headline-making romance with Maggie Sajak, daughter of Wheel of Fortune legend Pat Sajak, and then through his casting as the first Savannah Bananas player ever to compete on ABC’s Dancing with the Stars.

Early Life and Education

Jackson Daniel Olson was born on 6 October 1997 in New Milford, Connecticut, where he was raised, per Wikipedia and his University of Hartford roster profile. A three-sport athlete at New Milford High School — playing baseball, football and basketball — he specialized in baseball as a senior, batting .464 with 23 RBIs and 14 extra-base hits while leading his team to the 2016 conference championship game and the Class LL state semifinals, per Wikipedia. He earned First Team Class LL All-State honors and a spot on the Connecticut Hearst Media Super 15 All-Star team.

Olson played four years of Division I baseball at the University of Hartford, appearing in 161 games with a .288 career batting average and helping the Hawks to their first-ever America East Championship in 2018, per profile coverage of his college career. His academic record was equally strong: he was named the 2020 America East Baseball Scholar-Athlete of the Year and graduated with a Bachelor of Science in Business Administration, per thecityceleb.com. He then pursued an MBA in Marketing at Stetson University, where he played the 2021 season with the Stetson Hatters.

Career

Olson made his Banana Ball debut for the Savannah Bananas in 2022, per Wikipedia, establishing himself as a second baseman in the team’s infield. The Bananas — famous for marrying baseball with choreography, comedy and constant fan interaction — gave the self-described former “shy kid” the perfect stage. As he explained in a 2026 interview quoted by The Spun, he “never danced, never put myself out there, never entertained” growing up, and posting dance TikToks “just joking” led to a full-blown reinvention as a social media personality.

That reinvention is the core of his fame. Profile sites credit him with more than 1.6 million TikTok followers and over 79 million likes as of 2024, with viral clips of his energetic on-field dance routines doing the heavy lifting, per thefamousmagazine.com and celebrityinfolab.com. He also serves as an MLB creator and ambassador, connecting the sport’s audience to Banana Ball’s showmanship-first formula, per celebrityinfolab.com.

In 2026 Olson became the first Savannah Bananas player to join Dancing with the Stars, competing on the show’s 35th season on ABC while still fitting Banana Ball games into his schedule, per The Spun. The casting capped a year in which he also appeared in the first-ever Banana Bowl at Nationals Park in Washington, D.C. on 10 October 2026, where six Banana Ball Championship League teams — including the Bananas, the Party Animals and the eventual winners, the Texas Tailgaters — played an exhibition featuring a ninth-inning choreographed dance medley with the Jonas Brothers, per Time Bulletin. Special guests at the event included Kane Brown, John Cena and Pentatonix, plus DWTS cast members.

Personal Life and Relationship with Maggie Sajak

Olson’s off-field life has drawn as much attention as his dancing in 2026. According to reporting by People and TV Insider, he and Maggie Sajak — the country singer, Wheel of Fortune social correspondent and daughter of former Wheel host Pat Sajak — connected after attending the same Los Angeles Dodgers game, and had been dating since October 2025.

The couple hard-launched the relationship publicly on 21 April 2026 with a joint Instagram post: a photo in front of Cinderella’s Castle at Walt Disney World captioned “Applications closed” — a playful nod to Sajak’s earlier “boyfriend application” social-media posts, per TV Insider. Since then they have documented trips to Disney World in Florida, Disney’s Aulani Resort in Hawaii, and Olson’s Connecticut hometown, per People. In July 2026 Sajak accompanied Olson to New Milford when his hometown little league field was named in his honor, which he described on Instagram as getting “to share the moment with my parents, my girlfriend Maggie, and the baseball + softball players of New Milford,” per People. At the October 2026 Banana Bowl, Sajak cheered him on from the stands, posting Instagram Story footage of his introduction with “Let’s go!!!!” and joking “Like how is this real OMG?” as he shared the field with the Jonas Brothers, per Time Bulletin.

Jackson Olson Net Worth 2026

Jackson Olson’s net worth has not been officially disclosed, and no figure can be stated with confidence. Profile sites publish wildly differing numbers — thecityceleb.com suggests around $1.5 million while other low-credibility biography sites claim as much as $8 million — but none cite sources and none have been picked up by mainstream sports media. His income streams are the modern hybrid mix for a Banana Ball star: baseball entertainment earnings, social-media brand deals, content-creator partnerships including his MLB ambassador work, and, as of 2026, mainstream television appearances.

FAQ

Who is Jackson Olson?

Jackson Olson is an American baseball player, entertainer and social media personality born in New Milford, Connecticut. He is best known as a second baseman for the Savannah Bananas, whose choreographed on-field dance routines made him a TikTok star, and as a contestant on Dancing with the Stars Season 35.

What is Jackson Olson’s age?

Jackson Olson was born on 6 October 1997, which makes him 29 years old as of October 2026.

What is Jackson Olson’s height?

Jackson Olson is listed at 6 feet 2 inches (188 cm), a figure consistent across his University of Hartford roster profile, Baseball-Reference and his high school records, per usahousinginformation.com.

Who is Jackson Olson dating?

Jackson Olson is dating Maggie Sajak, the daughter of former Wheel of Fortune host Pat Sajak and the show’s social media correspondent. The couple went public with the relationship in April 2026, per People.

Is Jackson Olson on Dancing with the Stars?

Yes. Olson is competing on Dancing with the Stars Season 35 in 2026, making him the first Savannah Bananas player ever to join the ABC competition, per The Spun.

How did Jackson Olson become famous?

After joining the Savannah Bananas in 2022, Olson’s energetic choreographed dance routines performed during Banana Ball games went viral on TikTok, where he built a following of over a million — credited at more than 1.6 million followers in 2024 coverage.