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2. Tyler Chatwood
After the departure of Jake Arrieta and the retirement of John Lackey, the Cubs were in need of starting rotation depth. Prior to the 2018 season, one of their answers to this problem was former Rockies starter Tyler Chatwood, who was given a 3-year deal worth $38 million by the Cubs. Unfortunately, this wound up being a huge waste of money, as Chatwood proceeded to get absolutely shelled in his first year at Wrigley. Over 103 innings, Chatwood sported a wretched 5.30 ERA with a league-leading 95 walks.
A transition to the bullpen in 2019 saw a bit more success for Chatwood, but inconsistent performances and injuries mired his Cubs tenure. Since leaving Chicago, Chatwood has pitched with the Blue Jays and Giants, and he recently signed a minor league deal with the Pirates in December. I think I speak for most Cubs fans when I say his Cubs tenure best be forgotten.