Christmas is not a real deadline for transactions, and, for the most part, players and agents who’ve been willing to wait this long to sign are not going to be forced into an unappealing deal by an artificial cut-off. Ditto executives, even if they would love to be able to throttle down a bit for the holidays.
That said, it doesn’t have to feel like a hard deadline for everyone for it to feel like a soft deadline for some people. Each year, we do see some deals pretty clearly pushed to wrap up in the day or two before Christmas, I’d be surprised if that wasn’t the case again this year. Usually smaller deals.
The market I wonder about most, though, is the starting pitcher market. Obviously that’s primarily because it’s where the Cubs need to be shopping, but it’s also because it has been such a weirdly slow market after an early huge deal for Dylan Cease. Not only have so many of the top options not signed, we’ve barely heard a peep of a rumor on guys like Framber Valdez and Ranger Suarez, very little on Tatsuya Imai and Zac Gallen, and virtually nothing at all on the Chris Bassitt/Zack Littell/Nick Martinez/Lucas Giolito/Max Scherzer/Justin Verlander/etc. tier of starters.
The trade market hasn’t been much more active, with Sonny Gray going relatively early, and then mostly nothing but a few stray rumors.
Last week, though, we did see a little movement on both fronts. Michael King re-signed with the Padres, Mike Burrows was traded to the Astros, and Shane Baz was traded to the Orioles. In a few days, we saw more free agent/controllable starting pitcher movement than we’d seen over the previous month.
A series of one-offs, or maybe just a little bit of real movement ahead of the holidays? Could the combined impact of those moves opening things up, plus the soft Christmas deadline on Thursday, mean we see another move or two this week? Lordy I hope so.
My fear is that, at this point, and with every day that passes, the Tatsuya Imai posting could be a finger in the dam. We’re barely 10 days away from the posting being up, and we know the involved teams (especially the Cubs) are probably content to take this thing right up to the last second. That’s also true, I’m sure, of Imai’s agent, Scott Boras.
So if you take even just two or three clubs that are in the high-end pitching market, and you imagine they’re all stiff-arming everyone else until Imai’s situation is resolved, then it isn’t hard to imagine guys like Valdez and Suarez and Gallen all wanting to wait until they know which bidders are truly going to be involved for their services. And if they’re all waiting, that means even the non-Imai-involved teams are waiting. And that means even the starters in the next tier down would have to be waiting, too, and trade talks would be gummed up elsewhere as well. (Oh, and all of these things are all interrelated in other ways, too – for example, it’s not always that a team has a clean and straightforward Choice A, Choice B, Choice C flowchart of options; instead, sometimes it’s more like Choice A at this price, Choice C if at this price, but Choice B if at this price, and then Choice A if at this higher price, and so on and so forth.)
It can be hard for a deal to get done in that kind of environment, Christmas or not, when things will necessarily have to shake loose in 10-ish days anyway.
That doesn’t mean we won’t see a starting pitcher move this week. All it would take is a set of interconnected players and/or suitors who don’t realistically see themselves as impacted by an Imai fallout. Or, a team or player that simply wants to be aggressive and get something done now rather than wait on Imai and risk a worse outcome in January. That could happen, as we saw with King. Maybe he wanted things wrapped before the holidays, maybe the non-Padres teams were clearly not going to offer him more than they did, regardless of Imai or any other situation, and they decided to just finish the thing up.
As I type all of this, I realize what I’m really doing is pushing my own wishes out into the universe. Clearly, I want the Cubs to get a starting pitcher deal done this week, mostly so that (1) I can start thinking about how the 2026 Cubs look and the implications of whatever signing on what comes next; and (2) the Cubs don’t get left out in the cold next month. I understand that the Cubs might not even actually be waiting on Tatsuya Imai or related fallout. I understand that the Cubs might actually be waiting on Alex Bregman, for example, so maybe that’s where I should be putting my time-based wishes. It’s just that I’ve seen the front of the rotation as the bigger need/concern since the start of the offseason, so it’s where my default focus goes.
Despite those wishes, I’d be mildly surprised to see any of the top free agent starting pitchers sign before it’s clear what’s going to happen with Imai (even if not finalized), since that’s the actual hard deadline that looms. I guess maybe teams could use Imai’s deadline as a pressure tactic on another pitcher (“we have a bid in on Imai, and we might get him next week, so if you want to accept our offer to you first, you better get on it“), but even that’s still gonna require at least a little behind-the-scenes clarity on Imai.
In the meantime, I guess we stayed tuned on the rumors (including Bregman, because, yes, it’s not hard to imagine an outlay of that much cash impacting various teams’ other plans, including on the pitching side). The activity over the last five days has me optimistic that we’ll see something happen before Christmas, even if it’s not with the Cubs and a starting pitcher just yet.
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