One of the things discussed at length here and elsewhere in the wake of the Cubs' eight-year, $184 million deal with Jason Heyward is the idea that, right around the time that Heyward can opt out of the contract, the Cubs will be getting an infusion of many millions (if not billions) of dollars from the Cubs Network they are hoping to launch in 2020.
The Cubs' current TV contracts, a mishmash that currently has them shown on four different Chicago TV channels, all expire after the 2019 season. At that time the team hopes to bring all the games to you on one channel, similar to what the Dodgers have done in Los Angeles with SportsNet LA.