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With All-Star left fielder Ian Happ's three-year contract extension taking effect in 2024 with the Chicago Cubs, speculation has been that the team will view 2024, 2025, and 2026 as the next window for when the team will have clear expectations of being post-season contenders.
In his weekly hit on "The Bernstein and Holmes Show" on Audacy's Chicago Sports Radio, 670 The Score, Happ mentioned that the window for the team may expand beyond the next three seasons.
"The Chicago Cubs are in a situation now where there’s a bunch of good players. Everything is pointing to a very good team this year that has the capabilities to do a lot and then the continuation of a lot of those players still being here next year. I think that’s what they are trying to build here, a situation where it’s not a three-year window – the Chicago Cubs are going to be a good baseball team competing every year for a very long time."Ian Happ via 670 The Score
With the three-year extension of Happ along with the three-year extension of second baseman Nico Hoerner, it has become clear that the Cubs' president of baseball operations Jed Hoyer has learned from the mistakes of the past contention window of the team. During that window, the Cubs were hamstrung financially after the 8-year deal worth $184MM that the team gave outfielder Jason Heyward after the 2015 season.
While there certainly will come a point in time where the market would necessitate the need for the Cubs to give a lucrative long-term contract to a top free agent, the model that Hoyer is following should prevent the team from having off-seasons where they were handcuffed in spending as they were from 2018 through 2021. The Cubs have long-term financial flexibility as they embark on their next contention window and that certainly could lead to more sustained success for the team.