A star in both basketball and baseball at Washington State University, Hendrickson was drafted by both the NBA's Philadelphia 76ers and baseball's Toronto Blue Jays. Hendrickson elected to play basketball and joined the 76ers, playing in 29 games as a part time player. The 76ers let him go after the season and Hendrickson began a nomadic existence, playing part time roles with the Sacramento Kings, New Jersey Nets, and Cleveland Cavaliers.
In 2000, Hendrickson elected to abandon basketball and resume his baseball career, A pitcher, Hendrickson moved through the Blue Jays' minor league system and became a major league baseball player in 2002. He won three games late in the year and earned a starting role in 2003, when he posted a record of nine wins and nine losses.
Prior to the 2004 season, Hendrickson was traded to the Tampa Bay Devil Rays.