Lilly stepped across his body when he delivered his steep curveballs and fastballs. When he was forced into the rotation by an injury to Yankee starter Orlando Hernandez in 2001, he used his unusual mechanics to confuse batters and provided a string of strong starts in June and July. But Lilly heard the approaching footsteps of the healing Hernandez, and in August the strain showed in his pitching: none of his final four outings lasted more than four innings, and he gave up 16 earned runs in that span. When Hernandez returned, Lilly was sent down to Triple-A.
Lilly began his career in the Dodgers organization, but was dealt to Montreal in the July 31, 1998 trade deadline deal that brought Carlos Perez and Mark Grudzielanek to Los Angeles. He changed uniforms again in March 2000, donning pinstripes along with two other pitching prospects as embattled hurler Hideki Irabu was exiled to the Expos. Two years later, still a promising talent, he was sent to Oakland as the key bargaining chip in a three-way deal that netted the Bombers mercurial hurler Jeff Weaver, formerly of the Tigers.