Mandatory Credit: 9.newsachrive.com
#2 Roger Clemens, Toronto Blue Jays (1997) 4 years-$40 million
Roger Clemens has the distinction of being the only player on both sides of this list. After 12 seasons with the Boston Red Sox in which he won 192 games, the 35-year old Clemens was eligible for free agency for the first time. A long-time Red Sox, he had a tough decision to make. Most in Boston felt he was clearly on the downside of his career, boy were they wrong.
General Manager of the Red Sox at the time, Dan Duquette, was said to have offered more money than the Blue Jays did, but “The Rocket” decided to leave Beantown. He immediately paid off for the Blue Jays as he won back-to-back Cy Young Awards in 1997 and 1998. 41-13 with a 2.33 ERA and 1.061 WHIP was an excellent start to the contract. Two Cy Young Awards in two years was amazing, what else could you ask for? Guess they wanted more as Clemens was dealt after winning the second award.
Before the start of the 1999 season, Clemens was dealt to the New York Yankees for David Wells, Homer Bush and Graeme Lloyd. A pretty decent return, as it should have been since he was pitching so well. He wasn’t quite the dominant pitcher he was in Toronto, but the Yankees went on to win a pair of World Series in 1999 and 2000. Clemens did win another Cy Young in 2001. Total value on the contract was three Cy Young Awards and two World Series titles, not too bad.