A native of Park Forest, Illinois, Bailey won a junior freestyle crown at 132 pounds in Fargo in the summer of 2021. Bailey has been a presence since his days as a youth winning an IKWF state title in 2017 and following that up with a USAW folkstyle national title. Bailey closed out his youth career with a title at the NUWAY nationals and opened up his high school career with a fifth place finish at the Walsh Ironman tournament in 2019. Bailey finished the year with an Illinois state title in 2A at 120 pounds.