The New York Mets selected Clemens in the 12th round of the 1981 MLB Draft, but failed to sign him. Two years later, in 1983, Roger Clemens was drafted 19th overall in the first round of the MLB Draft by the Boston Red Sox. Clemens proceeded to break into the big leagues the following season and never looked back. In just his third season in the Majors, Clemens did something very few pitchers have ever accomplished, winning both the CY Young and the MVP.
Clemens went on to spend thirteen seasons with the Red Sox, winning three Cy Young awards and getting selected to five All-Star games. The Rocket became a free agent after the 1996 season and decided to sign elsewhere, joining the Toronto Blue Jays. Clemens’ stint in Toronto lasted only two seasons, both of which he won the Cy Young award. Following another brilliant campaign in 1998, the Yankees acquired Clemens from the Blue Jays in exchange for Homer Bush, Graeme Lloyd, and David Wells.
Clemens immediately made his mark in Yankees history, helping lead them to their 25th and 26th World Series titles in his first two seasons in the Bronx. Clemens once again won the Cy Young award, and helped lead the Yankees to another World Series in 2001. Clemens first stint with the Yankees lasted five seasons. Over that span, he helped lead them to four World Series and two championships. Clemens left for his hometown team, the Houston Astros, after the 2003 season and spent the next three seasons their until returning to the Yankees for one final season. It seemed fitting that Clemens ended his career with the team he won two titles with. When it is all said and done, Clemens will probably always be remembered as a Yankee thanks to those titles, despite playing eight more seasons with the Red Sox.