It was December 2006, and the Houston Astros were coming off an 82-win season in which they missed the playoffs for the first time since 2003. Roger Clemens and Andy Pettitte were leaving, so the roster needed some work. Enter the now-infamous Jason Jennings.
GM Tim Purpura made some bold moves early in the offseason, shelling out cash in free agency for slugger Carlos Lee and pitcher Woody Williams. In a move to further augment a starting rotation that had Roy Oswalt and a bunch of question marks, Purpura acquired Jennings and pitcher Miguel Asencio from the Rockies in exchange for pitchers Taylor Buchholz and Jason Hirsh and outfielder Willy Taveras on Dec.