This free agent continues to be connected to the Chicago Cubs

The Chicago Cubs' starting rotation depth may not be where the team is hoping with less than three weeks remaining before Opening Day.

Caleb Kilian is expected to miss the first half of the season, while veteran Jameson Taillon has yet to appear in a Spring Training game.

It's not an ideal position for the Cubs, considering many expect some form of regression from Justin Steele and Shota Imanaga beginning as the team's fifth starter as he transitions to Major League Baseball.

With Blake Snell and Jordan Montgomery remaining on the free-agent market, we are at the point where Scott Boras may have to settle for a short-term deal with opt-outs as he did with Cody Bellinger and Matt Chapman.

There likely is no scenario where the Cubs circle Snell as the opportunistic signing to add to the rotation, but Montgomery fits the profile of the pitcher the team has preferred to target. One competing executive told Jon Heyman of the New York Post that Montgomery is the perfect fit for the Cubs.

For a team that has the intention of playing meaningful games, the Cubs need to solidify their rotation.

For all the hope that Kyle Hendricks can build off his return to the pitching mound last season after undergoing extensive shoulder surgery, the fact remains that the Cubs chose to skip Hendricks against offensive-dominant teams such as the Atlanta Braves towards the end of last season.

Hope can not be the definition of expectation.

The Cubs may hope that a rotation that includes Hendricks and Jordan Wicks in his first full season will have success but to expect that would be a mistake. Adding Montgomery would give the Cubs another legitimate starter at the top of the rotation and then the bones of a post-season rotation can begin to be constructed.

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