Are the Chicago Cubs past the peak of their competitive window?

Chicago Cubs: Anthony Rizzo is the only one to sign an extension with the Cubs.

Further complicating this problem is the fact that the Cubs have, for the most part, been unable to convince any of their young players to sign contract extensions. These extensions would lock in some cost certainty as they would avoid the arbitration process.

Usually, the team saves some money in the long-term with these kinds of deals. The player guarantees himself life-changing money. The number of years of team control is usually extended, as well.

Really the only player current Cub to sign this kind of contract extension with the Cubs is Anthony Rizzo. If it wasn’t for his contract extension, Rizzo would be a free agent after this season. Instead, the Cubs hold a team option on his services for both the 2020 and 2021 seasons they will almost certainly pick up.

José Quintana is the only other Cub to sign a similar contract extension. But he signed that deal while he was still a member of the White Sox. The Cubs happily inherited the terms of that deal when they traded for him mid-season two years ago.