The Cubs’ “Cliff”…and I’m not talking about Cliff Floyd

As we wait for the Cubs to sign one big-name free agent, my thoughts have started to drift to the future. Specifically, 2027.

We already know that 2027 could be a tough year for baseball, with a work stoppage looming. I’ve heard or read zero indications that a deal will be made before the CBA runs out in December. We can only hope that the stoppage will occur during the offseason, as it did between 2021 and 2022, and would end in time to avoid the cancellation of games – but I fear both sides will be adamant on their opposite positions around the implementation of a salary cap.

So, I am not optimistic.

Here’s an article from ESPN about the upcoming labor battle: https://www.espn.com/mlb/story/_/id/47108752/mlb-labor-battle-cba-salary-cap-owners-players-union-mlbpa-faq-manfred

But even if the season takes place, things could get bad for the Chicago Cubs, with a situation described as “The Cliff” by the Cubs beat writers for The Athletic on the Northside Territory podcast: https://open.spotify.com/episode/1UdtgKBAINlQUsb3uhaimZ?si=8266c8530aca425d

As mentioned in the podcast, here is the list of Cubs free agents in 2027 (with a few recent additions):

• Shota Imanaga
• Jameson Taillon
• Matthew Boyd
• Ian Happ
• Seiya Suzuki
• Nico Hoerner
• Carson Kelly
• Colin Rea
• Hunter Harvey
• Caleb Thielbar
• Hoby Milner
• Jacob Webb
• Nate Pearson

So, 60% of the Cubs’ rotation, ~50% of the bullpen (depending on who makes the roster) and 44% of the starting position players.

One interesting quote from the ESPN article is Jed Hoyer’s position on the labor issue:

“Chicago Cubs president Jed Hoyer admitted at the end of last season that many of his player contracts were designed to be up after 2026 — in other words when the CBA expires — in order to have relatively clean books heading into 2027 and beyond. Several agents and teams believe that cost certainty in the form of a new CBA — and, if MLB gets its way, a first-ever salary cap — will return spending back to higher levels simply because teams will understand their yearly costs more intimately after a new deal.”

So it would stand to reason that the Cubs’ reticence around signing any big free agent deals could be due to the whatever the new CBA looks like.

One crazy theory I’ve that creeped into my brain is that Hoyer is attempting to prepare for the new labor agreement by making the roster as lean as possible so that the Cubs can take advantage of new limitations to player salaries, most likely in some form of salary cap.

There are still some teams spending freely this off-season – specifically the Dodgers, Phillies and Blue Jays. And the Mets, Red Sox, Yankees and Astros also having large salary numbers for 2027 and beyond. But 18 teams have less than $100 million currently committed to salaries beyond this season. And the Cubs are 17th in MLB at $66 million.

It would stand to reason that these smaller market (or fiscally cautious) teams would push very hard for a salary cap, which would almost certainly limit the big spenders in the future.

If there is a salary cap for 2027 and beyond, the big spending teams would likely have their hands tied. I could see them getting grandfathered in to allow them to maintain current contracts, but they may not be able to sign anyone new – similar to the rules around the NBA apron system. And it might prevent deferred money deals that they have used for almost every signing of the bug name free agents.

That would put any teams with money to spend in a great position to sign the free agents that are available for prices that will pale in comparison to the deals that are currently out there. If this actually comes to pass, it would be almost silly to spend current market value for Bregman, Tucker, Eugenio Suarez, Ranger Suarez, Valdez, Gallen or the other big remaining free agents. It would also explain trying to get something for Nico Hoerner, instead of trying to extend his contract. Or refraining fro extending the contract of any of the 2027 free agents.

Here are some of the big free agents in 2027 who are not Cubs:

• Tarik Skubal
• Freddy Peralta
• Ozzie Albies
• Michael King
• Trevor Rogers
• Luis Robert, Jr.
• Jazz Chisolm
• Shane Bieber
• Chris Sale
• Randy Arozerena
• Jesus Luzardo
• Brady Singer
• Brandon Woodruff
• Andres Munoz

So, theoretically, the Cubs could be extremely aggressive going after their own or other free agents in a market impacted by more financial limitations. And as one of the few big market teams in this position, they could make out like bandits. That’s the best case scenario.

The downside is that if the small-market owners cave, and the CBA does not go through any major changes, the Cubs will be in a similar position to where they were in 2022, as they simply could not field a competitive roster after losing a large chunk of their team – in that instance due to trades.

As a Cubs fan, having another “rebuild” so soon after 4 straight years of missing the playoffs would be very painful.

This whole theory could be blown up very easily if the Cubs sign a couple of big money free agents with longer-term contracts. But even then, they still will have lots of work to do to build a competitive roster in 2027 and beyond.

As we approach the MLB/Cubs “Cliff” of 2027, I’m really hoping the Cubs are like Road Runner, navigating it with perfection. And not Wile E. Coyote, crashing to the bottom.