The reality is with Ian Happ and the Chicago Cubs that if they don't get an extension done this winter, the only alternative (assuming he isn't extended toward the end of the year) is to trade him. Tough pill to swallow, and I've laid out why it makes zero sense to move on from a budding All-Star at a time when your competitive window is reopening.
It simply feels like a step backward at this juncture after an otherwise promising offseason. The Cubs have yet to come to extensions with their core players in the recent past. However, to Jed Hoyer's credit, let's consider that Kris Bryant was hurt last season, which unfortunately has become a common theme, and Javy Baez underperformed in his first year in Detroit. Anthony Rizzo signed a two-year $40.0MM deal with the Yankees this off-season, and he seems the only one that would have wound up being a good deal for the Cubs.
With Happ, the production is there at the right time. However, for an odd reason, if the front office feels otherwise, these three teams make the most sense to target the Cubs All-Star via trade this year.
Three trade targets for Happ - 3. New York Mets
The Mets make a lot of sense for Happ here simply because we know they are looking for a 4th outfielder. After the deal with Carlos Correa fell through, the Mets will likely continue with Eduardo Escobar at 3B and keep Jeff Mcneil at 2B instead of entertaining any idea of moving him to the outfield. Prospect Khalil Lee isn't ready for an everyday role at the Major League level, so the three guys are Starling Marte, Brandon Nimmo, and Mark Canha.
Adding in Happ gives the Mets a better outfield defensively while adding in that missing piece that can viably hit from both sides of the plate. The Mets seemingly don't care about payroll, and Happ's one-year left before free agency is perfect, with the rest of the money they have coming off the books next winter. The interest from New York will undoubtedly be there if Happ is made available, but the Mets will have to be ready to move a prospect that they are high on. The reluctance to do so at the trade deadline last season may be the issue that prevents any deal from happening here.