Today, Ken Rosenthal wrote up a set of interesting offseason notes that I think you’ll enjoy perusing. There was at least one thing he said that REALLY stood out, though, that I wanted to share some thoughts on:‘The Athletic’s Tim Britton projects a seven-year, $189 million contract for free-agent third baseman Alex Bregman. I suspect that Bregman and his agent, Scott Boras, are aiming higher — specifically, at a deal closer to the 11-year, $350 million extension Manny Machado signed with the San Diego Padres in February 2023.

’Rosenthal goes on to acknowledge how wild that sounds, how there is a statistical comparison available between the two players, and how Machado’s deal may have been inflated by the late Peter Seidler, who was spending freely for the Padres at the time. What I would add, though, is that (1) the Machado extension was seen as outrageously high at the time and has looked pretty darn bad since then, (2) Bregman costs draft pick compensation whereas Machado did not, and (3) Machado was coming off a three-year stretch of hitting 291/. 359/.

522/140 wRC+, whereas Bregman is at . 260/. 349/.

449/127 wRC+. In other words, I think Machado’s deal was absurdly too high *AND* I think he had way more value at the time than Bregman has now. Honestly I don’t even see why there’s a conversation here, and it’s important to note that Rosenthal says he “suspects” this could be sought, rather than reports that it has been asked.

It’s all almost too silly to even discuss. Though I could take a guess that maybe Bregman’s agent, Scott Boras, has been floating the comparison in one of his famous binders? And if he has, then it definitely becomes a discussion.

Sometimes Boras shoots for the moon. And hey, free agency means you get to ask whatever you want, right? Well, I don’t know that it is entirely accurate to say “it costs nothing to ask,” as we might otherwise say in these situations.

After all, we are not even a year removed from seeing EXACTLY what it can cost when the initial asks on free agents are outrageously high. Is Scott Boras making the same mistake this year? Is Alex Bregman (and maybe Pete Alonso along with him?

) about to be the next Matt Chapman or Cody Bellinger or Blake Snell or Jordan Montgomery? Those teams ultimately wound up not ABYSMAL for those guys, but I’m sure none of the four particularly WANTED to go into 2024 having to prove their worth again. And I’m also sure Jordan Montgomery thinks his process under Boras was a disaster, because he more or less said as much.

Now, to be sure, we don’t actually know for sure what Bregman and Boras will be seeking. We don’t know to what extent any of this is simply trying to push the Astros to get a deal done. We’ll see what develops when there’s more reporting on Bregman’s meetings with teams and/or actual offers made.

But I will say that even the mere mention of things like “11 years” or “$350 million” would seem so far outside the realm of possibility as to put up a roadblock for a team that even wanted to come with a serious offer. Like, if Boras ACTUALLY thought 11 years and $350 million for Bregman was achievable, then I’m certainly not going to bother with my version of what I think a reasonable offer would be (maybe something a little better than the six years and $151 million Chapman just got in an extension from the Giants? ).

Maybe I’m just the low man on Bregman given some of the trends under the hood, but I think going over $200 million – much less $300 million – could open you up to a whole lot of potential regret. Obligatory thoughts on the Cubs, since I know that’s where some minds will go given recent rumors … In a world where the Cubs traded Nico Hoerner, you could craft an argument that signing Bregman (to play second or third, with Isaac Paredes playing the other) is a way to get a solid offensive upgrade for the Cubs in the short-term. I would agree with that very specific point.

But I would not agree that the difference between Bregman in his 30s is so much greater than the projected performance of Hoerner PLUS Matt Shaw as an option PLUS James Triantos as an option that it’s worth the allocation of $200+ million in payroll. The Cubs need to spend the dang money, yes, but that’s NOT where I would spend it. If Hoerner is dealt, I’d want it to be because the value in return was really meaningful, because the Cubs want to open up a spot for Shaw/Triantos to compete, or because the Cubs are getting really creative and moving Michael Busch to second while adding some crazy big-time bat at first base like Vlad Guerrero Jr.

I just have no interest in seeing the Cubs dump Hoerner so that they can allocate huge long-term dollars to Bregman. Hey, maybe this all plays out such that Bregman does wind up having to be one of those guys taking a short-term pillow deal, and maybe we have some kinda wild conversation in February. I’ll at least leave that highly unlikely possibility on the table, as far as the Cubs are concerned.

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