2) Aaron Ashby
The Brewers brought have brought up a crop of interesting young pitchers roughly five seasons ago. Their system produced Corbin Burnes, Freddy Peralta, Brandon Woodruff, and Adrian Houser over a short period of time. As these pitchers acclimated to the major leagues, the Brewers quickly realized they had the makings of an elite rotation.
Depth players such as Eric Lauer, Brett Anderson, and Jordan Lyles were brought in as temporary stopgaps to keep the team afloat while they waited for their next wave of pitching talent, which included the likes of Aaron Ashby and Jason Alexander. Perhaps believing that these pitchers had the potential to become long-term rotation stalwarts, the Brewers acted aggressively and bought out Ashby's pre-arbitration and arbitration years, locking him into a fairly valuable deal worth over $20MM.
Since signing that contract, Ashby has been awful. Instead of growing into a reliable rotation arm, he's been awful. Ashby arguably took a step backward between 2021 and 2022, as his walk rate, home run rate, and batting average against all made noticeable increases. His strikeout rate also decreased significantly, though it remained elite. Ashby had trouble staying in games past the fifth inning and likely overtaxed the Brewers' bullpen. It's highly unlikely that he'd be making more money via the arbitration process than the Brewers are paying him.
Ashby hasn't pitched thus far in 2023. Reports are not forthcoming, but the information available suggests that Ashby may miss the full season. After experiencing inflammation in Spring Training, Ashby received a platelet-rich plasma injection but has been unable to play. Even if healthy, he may not have a guaranteed roster spot. His deal will eventually increase to $7.7MM during the 2027 season. This is a significantly lower dollar amount than that of Taillon, which is why Ashby takes second and not first on this list.