2. Trevor Bauer: Three Years, $102 Million, 2021
Not placing Bauer's monstrosity of a contract in the No. 1 spot is difficult, but ... the production was there, ever so briefly, in Year 1 of the deal back in 2021.
Bauer, coming off an empty-stadium Cy Young year where he experimented with spin rate in Spincinnati, went 8-5 with a 2.59 ERA in 107.2 innings, striking out 137 and popularizing the sword celebration. The signing didn't come without controversy the previous spring, when LA outbid the Mets at the horn to bring Bauer to California. The righty had a history of online bullying and didn't address his transgressions very satisfyingly before taking the mound in LA, instead meeting with a bullied child at spring training, a clear good deed that still seemed like a, "Hey, look over there!" at the time.
The worst was, of course, yet to come. Bauer was suspended in the summer of 2021 for 324 games (later reduced to 194) for his accused role in a sexual assault case. Further allegations followed in the initial complaint's wake, and Bauer has now found himself to be persona non grata in MLB after being released by the Dodgers this offseason.