Fifteen most regrettable free agent signings in the St. Louis Cardinals' team history, ranked from least to most disappointing

The St. Louis Cardinals are a powerhouse in baseball, boasting a rich history, legendary players, and a winning tradition that rivals only the likes of the New York Yankees. Despite their success, fans often find themselves left wanting more, and that's largely due to the team's hesitancy to open up their wallets.

Now, don't get us wrong, the Cardinals have every right to be cautious with their finances - they're a midsize market, after all. But the expectations in St. Louis are sky-high, and mediocrity just won't cut it. Rebuilds are simply not part of their playbook, and fielding a contender every single year is the bare minimum.

So why is the fanbase restless? Well, it seems the Cardinals' reluctance to make big-ticket signings is the culprit. While they excel at developing in-house talent and clever trades, their foray into high-profile free agent signings hasn't always been smooth sailing.

It's no secret that Cardinals fans love to dissect past management decisions, and let's face it - some of those decisions have been downright questionable! So, without further ado, let's dive into the murky waters of the team's signing history and uncover the 15 contracts that made Cardinal Nation cringe the most.

Too Soon to Tell: Steven Matz

Before we dive into the list, a quick word about Steven Matz and his four-year, $44 million dollar deal signed before the 2022 season. While it's tempting to include it in our list, basing a judgement on one injury-plagued season seems far too premature. At $11 million a year for a back-end starter, the deal isn’t an outrageous investment, provided Matz can stay healthy and perform up to par once again.

Enriching the Lineup: A Look Behind the Lists

In our hunt for the worst signing contracts in St. Louis' history, we've unearthed some interesting findings:

Matt Carpenter's Extension (2019): After a standout performance, Carpenter was handed a two-year, $39 million extension. However, his performance took a nosedive shortly afterward, leaving fans to question whether the team overextended themselves[1].
Miles Mikolas's Contract: Mikolas, a pitcher known for his erratic performances, has incurred fan ire with his high ERAs and a lack of strikeouts. His contract, while not explicitly discussed in the search results, is a point of contention[3].
Dexter Fowler's Contract: Fowler's name crops up frequently in discussions about unpopular signings, but specific details about his contract and performance are scarce in the available search results[1].
Paul DeJong's Extension: DeJong is another example of a player criticized for underperforming relative to his contract, but the search results don’t provide specific financial details[1].
Brett Cecil's Contract: Similar to DeJong, Cecil's contract didn’t yield the expected returns, yet the financial details are not outlined in the results[1].

To create a comprehensive list of the worst contracts, it's crucial to delve deeper into the team's financial histories, considering factors like performance relative to pay, contract duration, and any clauses that could impact the deal.

Some other contracts worth mentioning could involve longer-term deals that underperformed or became burdensome due to declining performance or injuries. However, specific details about these contracts are not readily available in the search results.

The St. Louis Cardinals, known for their success in baseball, are often criticized for their reluctance to invest in big-ticket signings despite being a midsize market. This hesitance has led to fan dissatisfaction, as the team is expected to field a contender every season. Notable contracts that have raised eyebrows include Matt Carpenter's 2019 extension, Miles Mikolas' contract, Dexter Fowler's contract, Paul DeJong's extension, and Brett Cecil's contract, all of which have been cited as examples of the team overextending themselves financially. These contracts, however, indicate a shrewd approach to the sports market, aimed at enriching the lineup rather than matching the spending of MLB powerhouses.