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#2 - Matt Carpenter: 2 years, $39 million, 2020
This is the hardest one on the list for a few reasons. First, Matt Carpenter should go down as a red jacket member for the Cardinals. He was one of the best players of the 2010s for them and was massively underrated nationally. Second, this contract could have been avoided altogether had the club waited a bit longer.
Hindsight is 20/20, but with an option for the 2020 season already in place, extending Carpenter was a bit premature. They replaced the $18.5 million option in 2020 with this deal and an $18.5 million vesting option for 2022.
During the life of the extension, Carpenter slashed .176/.313/.291 with 7 HR and 45 RB across 418 PA. He fell off a cliff hard and was a shell of the MVP candidate he was as recently as 2018.
It's really unfortunate that Carpenter would land on a list like this, and I hope Cardinal fans remember the nine incredible seasons he gave the team as his legacy, rather than the final two.