15 worst Chicago Cubs free agent signings in franchise history

14. Tyler Chatwood - 3 Years, $38 Million (2018)

In recent memory, there are few moves that prompted as much confusion from the fanbase as the Tyler Chatwood signing. In Dec. 2017, Theo Epstein and Jed Hoyer handed the right-hander a three-year, $38 million pact, despite the fact he was coming off a a 4.94 FIP and 1.442 WHIP, major league-leading 15-loss 2017 season.

Convinced they could turn his top-tier spin rates into effectiveness, the Cubs hoped he could add some overpowering stuff to the rotation mix. Instead, the right-hander led all of baseball with 95 walks in 2018, despite losing his role as a starter and being benched for essentially the last month of the season.

Chicago attempted to recoup some hope of respectability out of the Chatwood signing in 2019, when they transitioned him to a bullpen role - and he was definitely more effective there. He managed a 3.67 ERA as a reliever, also stepping in to make five spot starts on the year. He closed out his Cubs career during the fanless, shortened 2020 season - and it wasn't great, evidenced by a 1.661 WHIP and 10.6 H/9 in five appearances.