Ranking the 10 worst and most inexplicable Cardinals sagas under John Mozeliak

6. Sunk cost fallacy with bad extensions and free agent signings

Whenever the Cardinals did spend big money in free agency or by signing a player they developed to an extension, well, Mozeliak was very, very hesitant to admit defeat on those contracts, and it has cost the Cardinals both financially and in the win-loss column.

Let's take a trip down nightmare lane....and no, I'm not going to worry about putting these in chronological order or rank which were the worst deals.

How about Fowler and his aforementioned $82.5 million deal with the Cardinals? The highest bWAR Fowler ever put up for the Cardinals in an individual season was 1.7, and while he had an .851 OPS in year one of his deal, it ranked from .576-.754 in the three years following. It took until year five of the deal for Mozeliak to finally say enough is enough and eat the deal while shipping Fowler to the Angels.

The Cardinals signed Mike Leake to a five-year, $80 million deal prior to 2016, and he only made it one and a half seasons with the club before they had to dump his contract too. Leake posted a 4.46 ERA in 56 starts for St. Louis, a huge overpay for a player who, at best, was a middle-of-the-rotation starter but turned out to be worse for St. Louis.

How about the second Matt Carpenter extension? After eight incredible seasons with the club, Carpenter was in the final year of his first extension with the club, and midway through the 2019 season, the Cardinals extended Carpenter again, this time for his age-34 and 35 seasons.

Carpenter finished the final year of his first extension as a big league average hitter, posted a 79 OPS+ in year one of his new extensions, and finished out the 2021 season with a 63 OPS+ while continuing to play every day for the club. It was really bad, and it made his end with St. Louis (before returning in 2024) really sour for all parties involved.

Oh, and let's not forget Miles Mikolas, who, like Carpenter, Mozeliak extended early, and man, it's been horrible ever since he signed the dotted line. And yet, the Cardinals keep running him out there.

Brett Cecil, Greg Holland, Luke Gregerson, Paul DeJong, the list can keep going on. Mozeliak really struggles to part ways with bad investments, and it hurts the club big time.