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A few thoughts on the Cubs and the upcoming MLB trade deadline

Presenting an overview of where the team stands now, and where they might be headed over the next couple of weeks.

Photo by @WillByington /

It’s not lost on me that, as I write this piece, I’m much closer to Myrtle Beach, South Carolina than I am to Chicago, Illinois.

Two weeks from now, it’s quite possible that most of the best talent in the Cubs’ system will be closer to Myrtle Beach than Chicago, too.

The 2022 season has been truly bizarre. The Cubs have gotten superb production from their primary regulars at shortstop (Nico Hoerner), catcher (Willson Contreras), and left field (Ian Happ). There has been solid production at third base (Patrick Wisdom), right field (Seiya Suzuki), and from an emerging centerfielder-slash-rover (Christopher Morel). Two new young starting pitchers have emerged (Keegan Thompson and Justin Steele), and the bullpen has been led by a highly effective three-headed monster (David Robertson, Scott Effross, and Chris Martin). Add it all up and surely this team is battling for a spot at the top of the standings.

And yet, entering the second half of the season, the only meaningful question facing the Cubs over the season’s final two months is whether the club’s loss total will end up over or under 100.

Bizarre indeed.

Until we consider that the Cubs turned over most of their starting position player spots and cleared out their rotation, yet made only one foray into free agency for a medium- or long-term piece (Marcus Stroman) to fill in the empty rotation and lineup. Full-time gigs were handed to career minor leaguers (Rafael Ortega and Frank Schwindel) on the strength of their short-term auditions late in 2021 and their league-minimum salaries, and Jason Heyward kept his access to a full-time gig presumably based on his salary and “elder statesman” role. Starting pitching depth was non-existent, so injuries to Stroman, Kyle Hendricks, and Wade Miley quickly torpedoed the staff.

So here we are. The Cubs’ playoff odds have reached the disastrous 0.0%, which offers a stark reminder: based on what ownership and management told us during the offseason, the point of this season has always been to find pieces for the 2024 team onward. 2022 wins aren’t just superfluous; they actively cut against the goal of amassing future talent.

Of course, there is a way to retool on the fly as evidenced by the likes of Steve Cohen with the Mets and Guggenheim Partners with the Dodgers: spend into oblivion to paper over any organizational holes. But it’s quite clear that doing so isn’t the current approach of these Cubs.

And so, the reality of the Cubs’ organization is this: absent an unforeseen and unexpected desire to push payroll well over the luxury tax threshold, the Cubs’ best chance to win is by accumulating as much talent as possible on the roster of the Tennessee Smokies, South Bend Cubs, and even the Myrtle Beach Pelicans.

To be clear, this makes me sad as a fan. I love following the development of prospects and dreaming about the success of future rosters, but I have a massive preference for the Cubs trying to win while the farm matures, even when things don’t work out at the MLB level.

Nevertheless, the next step is inevitable: anything that isn’t tied down will be jettisoned for future assets. This means that Willson Contreras will soon be Yankee, Met, Astro, Cardinal (barf), or otherwise. Ian Happ — incredible redemption story and all — will soon wear another uniform. Much of the bullpen, including Robertson, Martin, and Mychal Givens, will find new homes on contending teams. If guys like Adrian Sampson (already 30), Ortega, and even Wisdom have value in the marketplace, they’ll likely end up elsewhere as well.

The loss of Contreras will hurt the most. He and Hendricks are the final major ties to the 2016 club, and Contreras has been one of the beating hearts of the ballclub for his entire tenure here. He’ll be a 32-year-old catcher with something like 6,000 MLB innings on his knees come 2024. There’s always a chance that he proves to be the exception and ages beautifully into his 30s, but the odds are higher that he is nearing the end of his highly-productive years. This management group is driven by the odds of success, so Contreras will likely take magical memories from 2016 with him when he leaves next week.

As I mentioned above, this does make me sad. But it primarily made me sad months and even years ago when it became clear that the 2016 core would exist only for a few years. This wasn’t going to be the late-90s Yankees, a core of guys like Derek Jeter, Bernie Williams, Mariano Rivera, and Andy Pettitte that stuck together through all of their useful years and continually pushed for October glory. When the big checks needed to be written, they’d be written by someone else (though I didn’t see Dick Monfort out in Colorado outbidding the Cubs for Kris Bryant!).

My attention has already been more focused on the farm this year, enjoying the exploits of Pete Crow-Armstrong, Owen Caissie, Caleb Kilian, Jordan Wicks, DJ Herz, Trey Ball, Cristian Hernandez, and, despite injuries, Brennan Davis and Miguel Amaya. There are even two big bats that have spent all year at Myrtle Beach drawing much of my attention: Kevin Alcantara and James Triantos.

In the coming days, we’ll take a look at some trade packages that could come back to the Cubs in exchange for some of their most attractive trade chips. Expect to see a whole bunch of potential new members of the 2022 Myrtle Beach Pelicans... and join me in dreaming about the 2024 Chicago Cubs. Like it or not, that’s what we have this year and probably next.