Chicago Cubs: Theo Epstein’s to-do list for 2017

Finalize the rotation before Spring Training

This isn’t an easy task, as things can happen in Spring Training that can change a team’s direction. But the Cubs seemed to have a plan once they didn’t pick up Jason Hammel‘s option for next season. Mike Montgomery–who pitched well for the Cubs–would slide into the final spot in the rotation. Then Tyson Ross was non-tendered and things seemed to “cloud” a bit.

The Cubs had pursued Ross the previous season, but couldn’t make a deal work. Ross had thoracic outlet syndrome surgery this year, which can be a difficult thing for a pitcher to fully come back from. Ross immediately became the most intriguing name in a pool of free agent pitchers.

I won’t say that Ross is the right option. But if the Cubs don’t re-sign the veteran free agent Travis Wood, Montgomery would be best left in the Cubs bullpen. If Wood chooses to pass on a potential starting gig and return to the bullpen for the Cubs, Montgomery will be a fine No. 5. There’s a lot of dominos that need to fall in a certain way, but the Cubs need to have this situation in order before heading to Mesa.