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3 pitchers in the Cubs' range - 2. Jordan Montgomery
Now a World Series champion, Jordan Montgomery enters free agency after posting a 3.20 ERA this year between St. Louis and Texas. A season ago, Montgomery notched a 3.11, so he certainly has a knack for consistency. Once he was traded to Texas, he posted a 2.79 in his 11 starts. Three years younger than Sonny Gray, Montgomery has more life left on his arm and also can be slotted higher into the starting rotation.
For the Cubs to land him, they must dig deeper into their pockets than anybody else on this list. For comparison, at five years, 127.0M, in terms of contract projections, Montgomery's AAV is around that of Marcus Stroman in the last two seasons. Still, having a rotation consisting of Steele, Montgomery, and Stroman in the top three spots provides the Cubs with three pitchers that can be ace-caliber on any given night.