Now in his early 30s, will his back hold up as he ages? If not, how much will it hinder him? And if Kershaw is looking to opt-out of $33 million and $34 million seasons each of the next two years, how much of a raise is he going to want? How long of a contract will he demand? Would the Phillies give a 31-year-old pitcher with a history of back problems a five or six-year deal worth $30-35 million a season, even if it is Clayton Kershaw?
Signing Kershaw would be a high-risk, high-reward maneuver, one I’m not sure this front office is anxious to make.