Westbrook's first three years with the tribe were fairly uneventful. He spent most of the first two years in the pen, making the occasional spot start when needed. His ERA with the lack of work was 5.84 over the two seasons, and it looked like the Tribe had ruined another pitcher by yanking him around.
In 2003, things would begin to change for Westbrook, in that the Indians would let him start more than relieve. The tenacious Westbrook would stay true to form even while continued to be bounced around between Buffalo and Cleveland, and between the pen and the rotation. Westbrook would finish the year at 7-10, with a 4.33 ERA. He started 22 games, relieved 12, had his first complete game, and pitched 133 major league innings.
Westbrook would actually start the year in the bullpen because of Bob Wickman's injury, but it would be his last time spent in the bullpen during his career. Westbrook not only would start in 2004, but he would essentially serve as the ace of the staff once he stepped into the role. Westbrook led the majors with five complete games, while going 14-9 with a 3.38 ERA. His ERA was the third lowest in the A.L., and he would pitch a career high 215 2/3 innings.
Westbrook would continue his steady hand in 2005 and 2006, winning 15 games in each year. In 2005, who would lose 15, with a 4.49 ERA. In 2006, he would lose only 10 games, with a 4.17 ERA. In that three year period, Westbrook would go 44-34 with a 4.01 ERA.
Westbrook would struggle in 2007 to start the year off, going on the DL on May 2 for nearly two months. He struggled prior to the DL-stint, but when he came back, he pitched some of the best baseball of his career. In the second half of the season, Westbrook went 5-5 with a 3.44, but in August, had a league best 1.90 ERA, while gong 4-1. While Westbrook was the only starting pitcher to struggle against the Yankees in the Division series, he was the most consistent starter in the ALCS, going 1-1 with a 3.55 ERA.
Westbrook would only start five games for the Tribe in 2008, and they would be his last starts of the Decade. Westbrook had been lights out during the spring, and this carried over to the regular season. He started the year off at 1-2, but had a 2.73 ERA. He would go on the DL, rehab, make one start that was decent, but get pulled. He would undergo UCL surgery in June, and wouldn't start again for the Tribe until 2010.
Overall, Westbrook went 63-62 with a 4.25 ERA, in 158 starts. He wasn't the Tribe's best pitcher, nor did he pitch the most games, but he certainly was the clue that kept this staff together.