Will the Chicago Cubs trade Kyle Hendricks, Willson Contreras and Ian Happ?

If Chicago Cubs fans thought the agony of the deadline fire sale was over, they may want to just hold off on going out and grabbing their new favorite player’s jersey until this offseason is over and the 2022 season is underway. Heck, it may last a little longer than that, but patience is a virtue, right?

Replete with more decisions on veterans, stars, thoughts of contention and the mystery of what the new CBA will hold for players and the front office, this could be one of the most intriguing offseasons that baseball fans have seen since the advent of free agency. Multiply that by a couple factors for the Cubs, a team that will seemingly still be in the lurch in 2022 barring some big surprises and splashes. Yet, that’s likely exactly what you’re going to be seeing and hearing about this offseason.

Will more Chicago Cubs core members be dealt this offseason?

Granted, Jed Hoyer (and, let’s be honest – the Ricketts who ultimately control the money) could still go several ways depending on how much money they’re willing/able to spend, what kind of position the new CBA puts them in, and how free agency plays out. Obviously, a pro-owners CBA would put the Cubs in a position to add more players more quickly, but other than continued words that the team is not “rebuilding” and will be looking to contend in 2022, we really have no idea what the intentions will be.

Could we see a 2014 repeat where the Cubs sign some vets to one-year deals in order to flip them and any other prime meat still left on the bone from the 2016 squad? Or will this be something completely different?

Either way, it’s very likely that some of what’s left of your favorite Cubs will not be with the team through this next window of contention. Let’s explore the possibility that Kyle Hendricks, Ian Happ and Willson Contreras might not be with the team next season.