This one's pretty simple. When he signed that contract he was coming off a year where he finished #2 in AL Cy Young voting. So he did have that leverage before he got to St. Louis and regressed into a bottom of the rotation innings eater.
It may be too late for him (at 36 years old) to fix his fastball velocity in the post-steroid era, but if he does have a bounce back year for the Red Sox that would have to make him an all-time reviled player in Yankees land since he infamously sucked for them but showed Cy Young quality stuff before and after in Oakland (2013-2015), Cincinnati (2019), and Minnesota (2022-2023). I'll always root for former A's to play well regardless but any chance to stick it to the Yankees is a nice bonus.
To be fair, we have a lot of pitching we need to pick up. Outside of Webb and Ray, it's the 43 year old FA Verlander and a bunch of unproven kids who haven't really shown they can maintain a rotation spot. Roupp is probably fine as a back-end starter, but realistically, we have 3 rotation spots open while our Bullpen is equally a mess. Randy Rod the only real elite arm we have and he's out all of 2026