It’s hard to fathom Clayton Kershaw not pitching for the Dodgers, but with free agency looming after the 2021 season, it’s at least a discussion that must be had. After finally winning it all last season, there isn’t much left for the future Hall of Famer to prove, but that doesn’t necessarily mean that he’s ready to walk away from the game.
During his recent appearance on Jimmy Kimmel Live, Kershaw was asked about his upcoming free agency and if he’s put any thought to possibly retiring in the event that the Dodgers win another World Series this season.
I think I will not retire, but I don’t know. If we won another [championship], Jimmy, that would be tough. I mean how do you top that? You’re just getting greedy at that point. But we’ll see how it goes.
With the Dodgers being the favorites to win it all, there is a good chance that Clayton will have to wrestle with this question all year. The good news is that there may be a wild card that could incentivize Kershaw to remain in LA: his childhood best friend and new Rams quarterback, Matt Stafford.
Kershaw and Stafford have been best friends since they were 8 years old and grew up playing sports together. Having his best friend now play in the same city as him is something that Clayton is looking forward to, and having him close by could potentially help influence his decision this winter. At least that’s the hope. But either way, expect Kershaw to enjoy every moment of it.
“And wouldn’t it be terrible for you to leave while your old friend since you were eight years old [is here]?” Jimmy Kimmel asked. “I mean it’s the kind of thing that makes you want to stay here ’til the end of your career, right?” “Exactly,” responded Kershaw. “Exactly.”
Clayton Kershaw on Dodgers Opening Weekend, Becoming a Free Agent & World Series Ring