Chicago Cubs: This winter should provide financial clarity

Chicago Cubs: Several players set to be free agents

For starters, the Cubs have several players on the roster that are on expiring contracts this season.

Part of the reason that the Cubs picked up Cole Hamels‘ option in the offseason had to do with the knowledge that he would be off the books after 2019. That opens up $20 million this winter.

Ben Zobrist will also be a free agent after this season. He is a good candidate to hang up the cleats anyway–particularly with everything that has happened in his personal life. But the Cubs likely would not re-sign him unless he took a one-year deal at a steep discount.

The bullpen offers the most opportunity for financial flexibility. Epstein may not have made big “splashes” this season, but he did well to take on contracts that afford the Cubs with options.

Both Derek Holland and David Phelps have team options for next season. So does Brad Brach, who has been incredibly underwhelming as the marquee addition in the bullpen this year.

Additionally, the Cubs will have multiple unrestricted free agents in Pedro Strop, Steve Cishek and Brandon Kintzler.

Strop is having his worst year as a member of the Cubs, but he is unquestionably one of the best relief pitchers in franchise history. Cishek and Kintzler have been two of the more effective arms in the bullpen this season. But there is still a high chance of turnover, as there is almost every season.