10 worst moves by St. Louis Cardinals John Mozeliak's front office since 2015

#7 - The second Matt Carpenter extension

Coming off of a top-10 MVP finish in 2018 and entering his age-33 season, the Cardinals decided to hand Matt Carpenter a two-year, $39 million extension with a $18.5 million option for the 2022 season. Mozeliak said at the press conference where the extension was announced, “The reason we were motivated to try to do this is because where he’s at in his career, we wanted him to continue to wear the Cardinal uniform.”

Had the Cardinals waited until the completion of the 2019 season to make this extension, they may had avoided a bullet.

The signs of regression came throughout the 2019 season, where Carpenter's OPS dropped from .897 in 2018 to .726 in the 129 games he played in. Over the course of the two years when the extension actually took place, Carpenter slashed just .176/.313/.291 with 7 HR and 45 RBI. Yikes.

While many have bashed Jeff Albert in recent years, Carpenter made some comments last season that indicated his resurgence since leaving the Cardinals had a lot to do with finally making some of the adjustments that Albert had recommended to him while he was still a Cardinal. Had Carpenter been more open to making changes to his swing during the 2020 and 2021 seasons, he may have been worth the deal he was given.

Instead, it ended up being a very sour end to an otherwise Red Jacket worthy Cardinal career for Carpenter. From 2012-2018, Carpenter was one of the best hitters in all of baseball, and hopefully, that is how Cardinals' fans will choose to remember him. But unfortunately, that doesn't change how bad his second extension was.