The Blue Jays selected Carpenter in the first round of the 1993 amateur draft from Trinity High School in New Hampshire, and he made his MLB debut in 1997. However, injuries and ineffectiveness delayed his career before the Blue Jays released him in 2002. After the Cardinals signed him, he emerged as an ace in 2004, winning the Cy Young Award in 2005 and helping lead the Cardinals to World Series titles in 2006 and 2011. For much of his career, Carpenter relied on his cutter that produced a heavy bore and finished with a sharp drop, a 12-to-6 curveball, and a sinker.