Ranking the 5 worst St. Louis Cardinals contracts in recent history

There have been some horrible contracts given out by the Cardinals in recent years, but who were the five that caused fans the most pain?

It’s January, and the lockout that has no end in sight. Rob Manfred just got Ken Rosenthal fired due to recent criticism and doesn’t even have a meeting scheduled with the MLBPA to negotiate the end of the work stoppage. Naturally, this makes for a great time to reflect on some of our favorite topics around the St. Louis Cardinals.

Terrible Contracts.

Yup, everyone’s favorite topic. On the more optimistic side, it was actually difficult to find more than five really bad contracts over the last five year period of Cardinal baseball. Sure, there were some that had mix results (Matt Carpenter and Carlos Martinez for example), but even both of these guys counteracted their brutal endings with All-Start level performances earlier in their deals.

But unfortunately, there are some really, really terrible contracts that president of baseball operations John Mozeliak has handed out over the last few years. Every executive makes mistakes, but some of these looked brutal the day of their signing, and aged even worse.

Let’s dive into the five of the worst contracts that Cardinals management has handed out in recent years.

No. 5: Miles Mikolas

In 2018, Mikolas became an All-Star and finished sixth in the Cy Young voting, he was handed a four-year, $68 million extension by the club. It’s hard to argue with extending a guy who went 18-4 with an ERA of 2.83 in over 200 innings of work, but Mozeliak probably wishes he had waited one more year.

In 2019, before his extension even kicked in, Mikolas went 9-14 with a 4.16 ERA in 184 innings. He missed the first season of his contract because of injury in 2020, and was only able to pitch 44 innings in 2021 to the tune of a 4.23 ERA and 1.21 WHIP.

Mikolas is due to make $17 million in 2022 and 2023, his age 33-34 seasons. Although there were some flashes of promise in his return this last season, it would be a huge surprise to see the Cardinals right-hander justify this contract over the next two seasons.

If we were to do these rankings again in 2023, there is a really good chance Mikolas moves up this list, but given the benefit of two more years to prove some value, he takes the No. 5 spot on this notorious list.

No. 3: Brett Cecil

Another brutal move from the 2016-2017 offseason, the Cardinals looked to strengthen their bullpen by adding left-handed specialist Brett Cecil to a four-year deal worth $30.5 million.

Although Cecil struggled a bit in the prior season, he had been one of the most consistent and top left-handed relievers from 2013-2015. If Cecil were to regain his from in St. Louis, he would have provided an elite left-handed option to an already strong bullpen.

That would not be the case, though. Across 100 innings in two seasons for the Cardinals, Cecil had an ERA of 4.86, with the especially horrendous 2018 that saw him post an ERA of 6.89 across 32.2 innings.

The contract and performance were so bad that the club released him after the first two seasons, paying Cecil $7.75 million in 2019 and 2020 to not play in St. Louis. He has not pitched in a big league game since, and it is pretty easy to see why.

No. 2 Mike Leake:

After being outbid in the last hour by the Red Sox for David Price and losing both John Lackey and Jason Heyward to the Chicago Cubs, the Cardinals made a classic panic signing by signing Mike Leake to a five-year, $80 million deal.

During his short time in St. Louis, Leake pitched 330.2 innings with an ERA of 4.46 and WAR of 1.5. Part of Leake’s downfall was his groundball pitching style on a ball club that ranked 28th in team defense in 2016, per Fangraphs, but did rise to a respectable level in 2017. Regardless, his career ERA before joining the Cardinals was 4.15 and his contract was a headscratcher.

While arguments have been made that the value that Leake provided was not actually all that bad, $16 million a year for a guy whose ERA with the team was 4.46 is nothing to celebrate and forced the Cardinals to hand him to Seattle just a year and a half into his deal and pay a large chunk of his contract for practically nothing in return.

No. 1: Greg Holland

Arguably the most disappointing signing in recent memory, the Cardinals signed All-Star closer Greg Holland to a one-year, $14 million deal on Opening Day 2018. After losing projected closer Luke Gregerson to injury and uncertainty in the bullpen outside of him, the club went big and brought in the best guy on the market.

And since Holland turned down the Rockies’ qualifying offer, the Cardinals had to forfeit their second round pick to Colorado in the 2018 Draft, while also losing $500,000 in international signing pool money. The club invested a lot in a guy who did not have a Spring Training, and did that move ever blow up.

Only 11 days after signing with the club, Holland would make his Cardinal debut on April 9 at home against the Brewers in extra innings. I had the privilege of being at his first outing, where only six of his 19 pitches went for strikes as he walked four batters and allowed one run while recording only one out on the day of work. Holland was met with a chorus of boos after only a few batters and left the field unceremoniously.

This was a preview of what was to come for Holland. In only 25 innings of work before being released on July 27, Holland posted an ERA of 7.92, WHIP of 2.24, and a with a record of 0-2 while blowing all three save opportunities. Although his ERA was rather high the season before at 3.61 (albeit, pitching in the pitcher graveyard of Coors Field), his 41 saves led the National League, making this failure of a deal even more of a headscratcher.