25. Anthony Rizzo, 2022: Two Years, $40 Million
Bet you didn't expect to see the contract Anthony Rizzo just signed crack this list, huh?
His $32 million contract inked prior to 2022 just missed, too, and Rizzo opted out, added an extra million dollars per year this offseason, and secured $6 million worth of guaranteed buyout money if the team doesn't pick up his final option year for 2025.
Worth it to keep him away from the Astros. Rizzo will be a de facto sub-captain for the Yankees under Aaron Judge moving forward, as long as his dog Kevin approves.