However, while Verlander ($20 million each of the next two seasons) and Hernandez ($39.5 million over the next two seasons) have already cashed in, Kershaw is playing on the second year of a $19 million contract. Yes, not exactly pocket change, although more than enough to have Bob Feller suggest Kershaw may have been good enough to pitch for the '54 Indians -- out of the bullpen, of course.
If there's a reason to suspect that Kershaw will never reach free agency, however, it's the announcement that former Cy Young winner Brandon Webb has retired at the age of 33. Like Kershaw, Webb was once one of the elite pitchers in the game, leading the majors in wins from 2005 to 2008 and winning the 2006 NL Cy Young Award and finishing second in the voting the next two seasons. Webb pitched just one game in 2009 but hurt his shoulder and despite repeated rehab and comeback attempts, never returned to the majors.
It's easy to forget how good Webb was, since he pitched those years in relative obscurity in Arizona. Despite the respect in the Cy Young voting, he always seemed underrated. An eighth-round pick in 2000 out of Kentucky, Webb walked 119 batters his first full season, but learned to command his hard sinker. In his Cy Young season he walked just 50 batters.
He pitched long enough to make $31 million in the majors and hopefully the Webb family is set for generations to come, but his injury shows how quickly the end can come for pitchers. Kershaw told the Los Angeles Times in late January that no long-term talks have taken place. "We'll see," Kershaw said. "I don't have any expectations."
Kershaw's hip started bothering him late last season, although he said he felt fine his final two starts. Still, it's at least a small warning sign, maybe just another reason to cash in now. Considering the Dodgers signed Zack Greinke to a six-year, $147 million and Kershaw is the better pitcher, you can imagine a talks starting at the $150 million. Sure, Kershaw would gain a few more dollars on the open market -- if he gets there injury-free.
As for Webb, he's just one of seven pitchers since 2000 to record at least three seasons of 6+ Baseball-Reference Wins Above Replacement.