Jackson Olson has been making a name for himself long before his romance with Pat Sajak's daughter Maggie Sajak. Olson is best known for his role as a social media personality and player for the Savannah Bananas. Amid the Bananas' growing online popularity, Olson has become a standout player on the team. The athlete has gone viral multiple times thanks to his Taylor Swift-inspired lip syncs and shameless ability to poke fun at his (once) lack of a dating life.