Clayton Kershaw
The one that would hurt most of all. Dodgers fans were losing their minds this past offseason when it appeared as if Kershaw might retire or sign with the Texas Rangers. When he returned, there was a collective sigh of relief that could be heard across the country.
He's on a one-year, $20 million deal for 2023. This offseason will mark the trilogy of Kershaw staring down the barrel of free agency. He insists he doesn't know what his future holds. He's expressed a desire to spend more time with family and be closer to home (which explains the link to the Rangers), but has also indicated there's unfinished business left with the Dodgers.
The three scenarios are re-sign with Dodgers, sign with Rangers, or hang up the cleats. The uncertainty might be the most detailed of the bunch, but it's also the most murky because it'll have nothing to do with Kerhsaw's performance.
It'll be up to how he's feeling mentally and/or physically after his 16th MLB season comes to a conclusion. So, please, savor every Kershaw moment this upcoming year, OK?