When the Astros signed Roger Clemens to come join his friend Andy Pettitte in the Houston rotation, few could have imagined just how successful that venture would be. He was 41 and coming off a six-season run with the Yankees in which he pitched to a 4.01 ERA, which was still above average considering it was the AL East in the early 2000s.
But Clemens exceeded expectations, going 18-4 with a 2.98 ERA in his first season with the Astros and taking home the 2004 NL Cy Young Award, his seventh such award.