7. DH Kendrys Morales - three years, $33M (2016-2017 offseason)
If it weren’t for two decent seasons at the plate, Morales would’ve found himself much higher on the list. He didn’t play out the entirety of the contract but performed admirably enough to warrant being lower on the list.
Morales had been an underrated player throughout his career. He was one heck of a power hitter and had little trouble being a productive big leaguer, it was just his health that was the biggest issue.
After a successful six-tenure as a member of the Angels, Morales spent time with the Twins, Mariners and World Series-winning Royals before signing a three-year, $33M contract with the Jays.
Respect to the Jays for making a “going for it” signing like this, but overall, this contract ended up being a bad one for the club.
Morales wound up playing in just two of the three years on his deal. He hit over 20 home runs and was at or above a 100 OPS+ but his contract quickly became an albatross and he was flipped to the Oakland A’s for next to nothing.
After the trade, horribly underperformed with both the A’s and Yankees before retiring at the conclusion of the 2019 season.