Cubs prospects may make an Ian Happ extension a less urgent matter

As it sits, the Chicago Cubs have more talent in their farm system than they have had in a long time. That group includes several young and upcoming outfielders in Pete Crow-Armstrong, Kevin Alcantara, Brennen Davis, Alexander Canario and Owen Caissie.

PCA, Alcantara and Caissie are still a ways away from big league action, but if Davis is 100 percent healthy and Canario is on the mend, it begs the question: will the Cubs' top prospects keep Jed Hoyer from offering top dollar in extension talks with All-Star outfielder Ian Happ?

Cubs seem unlikely to go outside their comfort zone in Ian Happ extension talks

In recent years, it’s no secret the Cubs front office has failed to reach contract extensions with any core players. Kyle Schwarber, Kris Bryant, Anthony Rizzo, Javier Baez and Willson Contreras have all departed from the organization via trade, free agency, or, in the case of Schwarber, a non-tender. Although Hoyer insists they wish to get deals done, particularly with Happ and Nico Hoerner, no one would hold it against you if you think Happ, too, will be walking at the end of the year. 

Chicago's the place that is home for me and the only thing that I've ever known. As a player who's only known this, you feel pretty at home in the organization and with the group. It would be weird to wear another jersey; I would love to stay here and I would love to be a part of the next great Cubs team, but we'll see.

I am usually the optimist in the room, but the ending of Happs message, “But, we’ll see”, strikes me with a bit of an ominous tone. Of course they have had contract extension talks, at least to some degree, but nothing seems close, and we’re well past the target date of having these talks moving closer to a deal. I’ve mentioned in the past that 2023 could serve as a “prove it” season for Happ, who could be poised for a massive payday - either from the Cubs or the open market - next winter.

Waiting until next winter to see what exactly Happ will bring on a year-to-year basis makes sense when you consider Davis' timeline on his journey to a potential MLB debut. But it's not without risk, either. Hopefully, the top prospect has proven he's healthy and ready to contribute at a big league level. If not, Hoyer could look to retain Happ, assuming another team isn't waiting to pounce with a big offer in free agency.

The funds are certainly there if the Cubs really want to extend Happ, evidenced by the spending spree Tom Ricketts bankrolled this past winter. However, that doesn’t mean you just back up the Brinks trunk simply because you can. It's definitely a fair question to ask: does the last one-and-a-half years of performance outweigh four-plus seasons of inconsistency?

A Happ extension gone bad wouldn't totally cripple the franchise - but we saw firsthand what $20+ million of dead weight can do in the Jason Heyward signing that went off the rails rather quickly. Keep in mind that, after 2023, that contract finally comes off the books for the club.

If it turns out 2022 was a fluke for Happ, Hoyer will be looked at as a genius for holding off on an extension. You can’t bank on prospects working out, but Happ’s inconsistency is surely a factor in the team not locking him up prior to this point. With a crowded outfield prospect picture, the price will have to be right - but if he's what he was last year, Happ is the type of player you make room for heading into a contention window.