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.