Back in early December, I made the case for the Cubs to open up extension negotiations with their homegrown ace, Justin Steele. Although Steele is already under affordable team control via arbitration through 2027 (his age-31 season), the projected price level of a deal he’d potentially be offered (based solely on some useful comps) was simply too reasonable to dismiss out of hand. The numbers thrown around at the time equated to a five-year, $74M extension (or a six-year, $96M pact), which would include his three upcoming seasons of escalating arbitration, before tacking on two or three additional years of control for $22M each.
And to that end, not much has changed: If Justin Steele is willing to go there, the Cubs would be foolish not to take advantage of that opportunity. Yes, you’d be guaranteeing him money several years before it was necessary, but Steele is on the sort of performative track that would push his next contract WELL beyond those levels.
For a little recent reference: Another left-handed free agent starter, Max Fried, hit free agency this offseason. And although he is a year younger than Steele will be when his time comes, he was also able to get $218M from the Yankees for his ages 31-38 seasons. So, yes, getting a few extra years of Steele when he’s at his best for $22M per year is, well, a steal.
In any case, that was just the beginning of the conversation. The Cubs and Justin Steele hadn’t yet opened up any negotiations, nor were they expected to. But we did think that conversation might happen in January (i.e. now), when the arbitration cases were being made. Alas, the Cubs and Justin Steele avoided arbitration for 2025 (actually a good thing). And according to the man himself, those talks did not include any discussion of an extension.
Here’s an exchange from the latest episode of the Locked on Cubs Podcast, where Justin Steele was asked point-blank about the Cubs’ efforts.
QUESTION: Have you spoken to the Cubs about (a contract extension)?
Justin Steele: Uhm, I mean, no. Me, personally, I haven’t had any discussions or conversations as far as that stuff goes….It’s something that hasn’t been brought to me from the team or anything. But, I mean, if it’s something that was brought to me, in front of me, I would sit down, look at it obviously and take it into serious consideration and decide what made sense for me and my family at that point.
But to answer your question, no, nothing’s been brought to me.
And here’s another from the North Side Bound Podcast:
Justin Steele: “There wasn’t any type of (extension) discussion or conversations like that. I didn’t even speak to Jed (Hoyer) or Carter (Hawkins). It was mostly the Cubs negotiation team….Ever since we agreed on the arbitration number, there hasn’t been any further conversations. I imagine if that conversation is going to be had, it’ll be during Spring Training….
Well, there you have it. To be sure, I’m not at all surprised it wasn’t brought up yet. Not only are the Cubs (under Jed Hoyer) notorious for waiting as looooooooooooong as possible to make this sort of decision (and we’re still several years away from it being a necessity), but also there wasn’t even an arbitration salary debate to help nudge things along. Perhaps they’ll open up this sort of conversation during Spring Training? I guess we’ll see, but I tend to doubt it.
But here’s the bottom line: Under normal circumstances, I’d be hard-pressed to imagine any world in which Jed Hoyer opens up extension negotiations now for a player under control for three more (prime-age) seasons. The question, then, is Are these normal circumstances? IF Justin Steele is open to a deal in that reported range, it represents (potentially) significant value to the Cubs. The sort of value Jed Hoyer wouldn’t want to ignore.