“We knew the 2017-18 offseason would be one of our most challenging,” Theo Epstein told us hours after the Cubs lost in the NLCS.
The upcoming months will be challenging for a variety of reasons. Jake Arrieta and John Lackey’s potential departure leaves the Cubs with two gaping starting pitching holes. Then you’ve got first-year arbitration salaries for Kyle Hendricks, Addison Russell, and Kris Bryant, signaling that realistic talks for extensions are fast approaching. And Joe Maddon’s already volatile bullpen could be devoid of a lock-down closer with Wade Davis entering free agency. Even my OOTP teams don’t have this much going on during an offseason.