1999, he went 11–5 with a 3.92 ERA in 27 starts for the Harrisburg Senators, the Double-A club in the Eastern League. Following three consecutive 27 start seasons, Westbrook was traded in the off-season. On December 22, 1999, the Expos traded him with two players to be named later to the New York Yankees for Hideki Irabu. (Montreal Expos eventually sent Ted Lilly (March 17, 2000) and Christian Parker (March 22, 2000) to the Yankees to complete the trade.) The Yankees assigned Westbrook to the Triple-A Columbus Clippers in the International League. He went 5–7 with a 4.65 ERA in 15 starts. New York Yankees (2000) Westbrook made his spring debut and allowed 3 runs in 3 innings, still Joe Torre was pleased with what he had seen from the 22-year-old Westbrook. In his major league debut on June 17, 2000, and his first start at Yankee Stadium for the Yankees against the Chicago White Sox, he did not make it past the second inning. He appeared in three games for the Yankees as a rookie, two starts and once out of the bullpen, going 0–2 with a 13.50 ERA. Cleveland Indians (2000–2010) On June 29, 2000, the Yankees traded Westbrook with fellow sinker ball pitcher Zach Day and outfielder Ricky Ledée to the Cleveland Indians for outfielder/designated hitter David Justice in their quest to eventually win the 2000 World Series. However, Westbrook cracked a rib at some point while he was pitching, so his 2000 season was cut short. In 2001, the Indians invited him to spring training. He shuttled back and forth between Cleveland and Triple-A Buffalo Bisons in the International League. He did well in Buffalo, amassing an 8–1 record in 12 starts. But he struggled with his role, going a lackluster 4–4 in Cleveland out of the bullpen and in six spot starts. In 2002, Westbrook caught a break. He became a regular part of the Cleveland pitching staff that was in transition, as the Tribe went 74–88, finishing 3rd in American League Central Division and getting coach Charlie Manuel sacked midway through the season (76 games). He also signed a three-year contract with the team. For the 2003 season, Westbrook converted back to starter, going 7–10 with a 4.33 ERA, ending the year as the team's fourth starter. After beginning the season in the Indians bullpen, Westbrook earned a spot in the Indians rotation in