Initially, some believed the Chicago Cubs should have let Cole Hamels hit the market and re-sign him to a team-friendly deal. That is no longer the case.
If the Chicago Cubs wanted to keep Cole Hamels for 2019, they had to pick up his $20 million option. It might have been reasonable at one time to hope that the Cubs could have re-signed Hamels as a free agent to a more team-friendly deal. But the early indications of this offseason are that in this pitching market, a free agent contract for Hamels would have been a worse choice than picking up his option.
The Cubs front office probably tried to negotiate a contract extension with Hamels before the deadline for making a decision about his option. Hamels said that he was open to a contract extension with the Cubs.
The kind of contract they would have been offering would have paid Hamels less per year than his $20 million option, but it would have had more guaranteed money because it would have been for multiple years.