The Chicago Cubs almost began 2017 with Montgomery in the starting rotation. Jason Hammel‘s option wasn’t picked up. Instead, the Cubs signed Brett Anderson. During spring training, Anderson and Montgomery competed for the last spot in the starting rotation. Eventually, it was decided that Anderson would be the starter and Montgomery would begin the year in the bullpen. However, Anderson was terrible and it wasn’t long before he was injured too.
When Montgomery got his chance as a starter, he was good. In 2017 Montgomery pitched 69 1/3 innings in 14 starts.