Chicago Cubs: Theo Epstein learning from Dave Dombrowski’s failures

Chicago Cubs: Time to rebuild the farm

The Red Sox depleted the farm in the pursuit of a championship. The Cubs did the same in the hopes of staying on top. Now both are in dire need of premium prospects.

There is a real possibility that Boston’s own window is on the verge of closing. Betts is likely to be gone next winter if not this offseason, and the sheer lack of arms in the minors will doom them after the way this past season went, especially if Sale eventually needs surgery.

Henry and the Red Sox are very cognizant of this, which is why they fired Dombrowski (just one year after winning the World Series) and hired Chaim Bloom–a former Rays executive and master of navigating payroll or lack thereof–to take his place.

Theo is almost certainly cognizant of how this applies to him, as well. With Ricketts insisting the Cubs should be competitive without windows and Epstein’s contract expiring after the 2021 season, it makes sense that there has been so much talk about change and restructuring.

Baseball is a copycat league. If Theo cannot find a way to acquire assets for the future while remaining competitive, then his days in Chicago are numbered.