By the end of the 2023 season, Clayton Kershaw will almost definitely (knocking on a million pieces of wood, chopping down full trees just so we can knock on more wood) occupy the No. 2 spot on the Dodgers' all-time wins list.
At that point, capturing the record will simply be a matter of how long he'd like to do this (and whether he believes his career has one more southern-flavored pivot in it).
Kershaw, sitting at nearly 35-and-a-half years old, has held up reasonably well. While he's been dinged and bruised, he continues to manage his workload and ailments the the point where he's still remarkably effective when operational. Fresh off plowing through the Brewers on Wednesday night for his 11th win of the season and 208th of his career, the generational left-hander now sports a 2.48 ERA in 105.1 innings, good for 3.3 bWAR.
It's doubtful he'll ever top 150 innings in a regular season again, but what foolish team (with ample resources) wouldn't give him carte blanche to toss those 150 exceptional innings while wearing their jersey?
At this point, Kershaw will likely have the option to return to the Dodgers on one-year deals for as long as he'll have them; the decision about whether to stay, go to Texas, or head off into the wild Dodger Blue yonder rests on his shoulders. He may be tempted to stay in LA until his career wraps, though, by the team's resurgence, Shohei Ohtani's rumored arrival, and his proximity to the all-time franchise win record. After Wednesday's win, he's two victories away from passing Don Drysdale for second, and only 26 wins from eclipsing Don Sutton for the top spot.
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Dodgers All-Time Wins Record: Clayton Kershaw about to claim No. 2 spot
It seems doubtful that an individual accomplishment could be the deciding factor in Kershaw choosing to lengthen his career. He's racked up more than enough victories, both moral and actual, and will be viewed as an all-time world historic Dodger if he never wins another game.
That said ... he's extremely close to being able to lay permanent claim to the top spot, and with the Dodgers and Texas Rangers running neck and neck for relevance at the moment, he wouldn't be sacrificing a shot at a ring to stay put, either.