Rupe made his major league debut in 1999 for the Devil Rays, pitching in 24 starts while finishing with an 8-9 record. The following season, Rupe had a horrendous season while battling with knee problems. Rupe finished the 2000 season with an ERA of 6.92, 75 runs allowed in 91 innings and 19 home runs allowed in just 18 starts.
In 2001, Rupe managed to pitch in 28 games (26 starts) for the Devil Rays but with awful numbers. In 143.1 innings, he allowed 30 home runs and 111 runs to go along with a record of 5-12. His ERA finished at 6.59, the following season, Rupe recorded a decision in all 15 starts he had, going 5-10 during that stretch. He was released following the season.
Rupe ended his Devil Rays career with a 23-37 career record.
Rupe signed a minor league contract with the Boston Red Sox. Rupe spent the majority of the season at the AAA level, appearing in just 4 games for the Red Sox towards the end of the year.
- Career statistics and player information from Baseball-Reference, or Fangraphs, or The Baseball Cube