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In the days leading up to the 2025 MLB trade deadline, Cubs fans talked almost constantly about the chances that the team would acquire a frontline starting pitcher controllable beyond 2025. In a summer trade market that featured only mid-tier rental starters, the jewels of a potential deadline bazaar were Washington's MacKenzie Gore; Miami's Edward Cabrera and Sandy Alcántara; and Minnesota's Joe Ryan. The Cubs themselves focused on various high-end players with team control beyond this year, too, but ultimately, they acquired four players (Willi Castro, Andrew Kittredge, Taylor Rogers and Michael Soroka) who will all become free agents this fall.

None of the four quasi-aces named above were dealt at all by the end of July, so the Cubs were not alone in finding the price tags on each (especially Gore and Cabrera, on whom they had the most active discussions) exorbitant. Chicago also checked in on controllable relief aces Jhoan Duran and Mason Miller, who were traded, but didn't come close to acquiring either flamethrower, sources familiar with their deadline discussions said.

Interestingly, though, teams who talked to the Cubs about players (all six of the names above, as well as some others) under team control through either 2027 or 2028 came away with the impression that the team was assigning little value to those years. There are multiple reasons why a team might feel that way, including the baseline injury risk for all pitchers, the nature of even high-end relievers as long-term assets, and the specific medical histories of a few of the arms in question, but one high-ranking front office member with another team felt that the uncertainty of labor relations between the league and the players union played a role in their thinking. Behind the scenes, the threat of a lockout that could curtail or distort the 2027 season (and the promise of a salary cap for which the owners intend to fight, which is why a lockout appears so likely) is a constant talking point, and it did color some trade talks throughout the league last month.

"We just felt, if we're going to move this player, the return has to reflect the fact that they're under control at a below-market price [through those seasons]," said the source, who spoke on the condition of anonymity because they are not authorized to discuss details of trade conversations. They went on to say that the Cubs' counteroffers and the tenor of their expressed interest "didn't seem to acknowledge how valuable those years are."

The source said neither the possibility of a lockout nor the uncertainty about the financial landscape of the game beyond 2027 was directly discussed, and could only speculate about the Cubs' motivations in discounting those seasons more heavily than the would-be selling team did, but they had a specific sense that the term of team control in question was being weighed differently by the two clubs. 

A source briefed on the Cubs' internal discussions said the specter of a lockout was not explicitly named as a reason to reduce offers or hold hard lines on any given players, but that "uncertainty about the system" beyond 2027 was a consideration. 

At first, this might seem to clash with the idea expressed by GM Carter Hawkins in the wake of the trade deadline.

"Teams are trying to find that guy that can lock down the eighth or ninth inning, but that also costs a lot. That costs a lot of future wins," Hawkins said in a post-deadline interview with ESPN. "We have a responsibility to the 2025 Cubs but also the 2032 Cubs. That’s not always popular in the moment, but it’s decisions we have to make."

Hawkins, though, was talking about weighing the present against the future—in the context of players, like top Cubs prospects Owen Caissie, Moisés Ballesteros, Kevin Alcántara, Jaxon Wiggins and more, who will be under extremely low-cost team control through at least 2028 and can't become free agents until at least the fall of 2031. In the eyes of the team, those players' value will be relatively unaffected by any disruption to 2027 and by the possibility of changes to payroll caps or competitive-balance measures under whatever new Collective Bargaining Agreement is implemented thereafter.

By contrast, for players who will hit free agency after either the 2027 or 2028 seasons and who might have hefty salaries for those years even via arbitration, the implications of even a partial reduction of the 2027 season or of changes to payroll and draft compensation rules could be hugely significant. It's fair, perhaps, to view the Cubs as valuing the 2025 and 2026 teams as very important; the 2029-32 teams as very important; and players whose pivotal contributions might come in 2027 and 2028 as somewhat harder to assess. 

The particular construction of this team might have led them in that direction especially forcefully. They were never all-in on 2025, but they're very much all-in on the two-year window comprising this year and next. After next year, Ian Happ, Seiya Suzuki, Nico Hoerner, Matthew Boyd, Jameson Taillon and Carson Kelly are all due to hit free agency. Dansby Swanson, 32 next February, is under contract through 2029, but is likely to have to move to second base by 2027. Shota Imanaga's contract contains a complicated option on which the Cubs must make a decision this fall, but is likely to end up being in a Cubs uniform through 2027. Imanaga turns 32 on Sept. 1, though. Justin Steele is under team control through 2027, too, but his future is entirely uncertain after his Tommy John surgery in April.

Pete Crow-Armstrong, Michael Busch, Matt Shaw, Miguel Amaya, Cade Horton and Daniel Palencia are the long-term core of this team, all under control at least through 2029 and all looking like solid contributors. With so much uncertain beyond 2026, though, the Cubs took a cautious approach at the trade deadline. They intend to try to win this year, and next, but they elected to remain extremely nimble and to maximize organizational depth for at least one more acquisition period. This winter, it will be interesting to see whether their decisions about pursuing Kyle Tucker in free agency and otherwise loading up for the final year of the Happ-led veteran group are as colored by the looming questions about the years thereafter as their activity at this trade deadline appears to have been.


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I think it's worth noting that this attitude towards '27/'28 would make just as much sense without the CBA expiring.  You touch on why in your second to last paragraph.  The team has practically no money tied up post 2026.  Based on roster resource, it looks like this:

- Swanson's $28M is rock solid guaranteed

- Shota's $15M will probably get picked up

- Steele in Arb 4, let's call it $10M

- Assad at Arb 2, I'd be shocked if that's much north of $5M

- Amaya, Busch, PCA, Hodge, and Palencia at arb 1.  Barring some incredible developments none of those guys except PCA will top $5M.  PCA might approach 8 figures

So the team's got ~$100M in LT payroll committed in a year where the LT line is going to be at least $245M, and 1/3rd of that isn't even guaranteed.  Even conservatively that's $100M available to sign players for the FO.  Contrast that to this winter, where there's ~$50M available by the same assumptions, and a Tucker pursuit would take up most of the available cash on its own.

An Edward Cabrera making ~$5M next year and projected for ~3 WAR is hugely valuable given the likely financial limitations.  In 2027 though, there's not that same financial calculus because the marginal value of a dollar saved is pretty low.  Ditto 2028.  He's not worthless after next year, but if you did some $/WAR calculus I'd bet 80+% of the utility in a trade would have projected to come these first 15 months.  Gore and Ryan, under control one fewer year, it'd have been more stark.

I also kind of wonder if the prospect timelines influence this too.  '27 is probably when you'd start to prefer having e.g. Wiggins and Caissie than Cabrera.  So from the Cubs' POV I could see an argument that "you have to make things really worth it for us up front because we're going to lose the back half of the deal", almost like a FA contract.

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