2. Homer Bailey, Cincinnati Reds, 2014-2018, -1.4
When Walt Jocketty signed Bailey for six seasons at $105 million, it was done with great fanfare, Bailey had gone only 11-12 in 2013 and he carried only a 49-45 career record, but both of those figures were seemed as more of a reflection of the team’s record than Bailey’s lack of talent.
In fact there was no question about his stuff. He pitched a no-hitter in 2012, then pitched another in 2013. The issue, as the Reds would in short order learn, was his health.
In 2014, Bailey made 23 starts, but chronic arm fatigue sidelined him in August with a 9-5 record. He returned in 2015, but was sidelined again in May and underwent Tommy John surgery to repair a torn UCL. He came back in 2016, but made only six ineffective starts.
Another surgery, this time for bone chips, delayed the start of Bailey’s 2017 season until June. He did manage 18 starts, but again was ineffective, going 6-9 with a 6.43 ERA. In 2018, he was healthy, but suffered through a 1-14 season and another ERA above 6.00.
Bailey’s then, is the classic cautionary tale about giving long-term deals to pitchers. In the two seasons prior to signing that contract, he averaged 208 innings. Since then, he’s averaged just 75 innings per season, and they’ve been horrible innings.