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.

Chicago Cubs: Ian Happ’s performance is maddening at times

Is Ian Happ a different version of Kyle Schwarber in disguise? Other than the body type and Happ’s ability to switch hit, the two guys have a lot in common. Sure, Happ is faster and a bit more athletic in general than the now-Red Sox left fielder, but there’s something in their tools and inconsistency that just makes them maddening for such a large percentage of fans. Neither one really has a position they are great at, although Happ has had more positional flexibility, even if he doesn’t play any of them particularly well.

Happ is a tease for anyone who watches him during hot streaks like he’s currently in right now. Same could be said of Schwarbs when he was with the Cubs as well, although he’s put together a mostly consistent and phenomenal 2021 season with the Nationals and Red Sox so far. Happ’s explosive power, especially to the left-center gap as a left-handed hitter is special, his eye and command of the strike zone is excellent, and his speed on the bases is a plus. He’s also a really likable character and one of the few guys fans can cling to with all of the departures.

And yet, there’s the plummet off the cliff for large stretches with Happ that suggests he isn’t ever going to fully and consistently figure it out. It’s infuriating and seems to defy logic, but how can a guy bat .170 for a large part of the year and then all of a sudden flip a switch and look like an MVP? I like Happ, and I’m not saying I don’t want him on the Cubs, but look what a fresh start and a “kick in the pants” did for the World Series hero Schwarber.

If another club really likes what Happ brings to the table and thinks they can harness his abilities consistently, the Cubs will most definitely listen given the fact Happ’s arbitration number will be going up and that he only has two more years left of club control.

Chicago Cubs: Will Willson Contreras be behind the plate at Wrigley in 2022?

A couple years ago, and maybe even last offseason, the Cubs were no doubt hoping that Miguel Amaya would be having his cup of coffee in Chicago at this point and then be ready to take on a more substantial role on the 2022 team.

Unfortunately, after a middling start to the season in the minors and an injury that has had him out for the last couple months, it’s possible, Amaya doesn’t even get to the bigs until 2023. And, while that could still line up with a Contreras exit to test free agency after next season, that’s not really what anyone would bet on at this point.

So, the questions stands, what do the Cubs do with Contreras? Clearly, the guy is now the emotional leader of the squad with Javier Baez and Anthony Rizzo no longer in the picture, although their hasty jettison also paints a hazy picture for Contreras himself. With no extension in place, how is Contreras any different than those other two, especially heading into his own walk year?

My guess is the Cubs will try and extend him, if for no other reason than he’s here, he’ll be a positive leader in the clubhouse, and he’s still one of the best offensive catchers in baseball when healthy. However, if Opening Day gets closer and closer and the Cubs still have not extended him, the writing is on the wall, as it was with the guys offloaded in the most recent midseason fire sale.

As noted, so much depends upon the CBA and changing landscape of the league/team this year, but it’s sure to be a busy and interesting offseason for the Cubs, if nothing else.