#5 - Dexter Fowler signing
If you thought the beginning of the list was cringe worthy, get ready for the rest of the moves to come.
Dexter Fowler was fresh off being the lead-of hitter for the World Series Champion Chicago Cubs. The St. Louis Cardinals needed both a center fielder and a lead-off hitter. Match made in heaven, right?
I remember when they announced the five-year, $82.5 million deal with Fowler and being beyond frustrated with the deal. From 2008-2016, Fowler, has a 107 OPS+ and made his first career All-Star team in 2016 at age-30. Fowler wasn't a bad player by any means, that's a valuable player for any team. But handing him that big of a contract, and going into his age-31 season, seemeed like a disaster waiting to happen.
2017 was actually a very good year for Fowler, although he only played in 118 games. He slashed .264/.363/.488 with 18 HR and 64 RBI while playing pretty good center field for the Cardinals. But 2018-2020 were terrible years. During that stretch, Fowler slashed .218/.320/.370 with 31 HR and 113 RBI over the course of 271 games. He could no longer play center field either, finding himself out in right field most days. The Cardinals ended up trading Fowler to the Angels before the 2021 season, absorbing most of his $14 million salary.
In a vacuum, this move could be higher on the list, but I feel better about "burning cash" as a club than trading away young assets, which is why some of the trades outrank this highly for me. There is one more signing I would critique even more than this one, and you'll see why in a moment.