Wooooooof. If this story from A.J. Pierzynski is accurate, then the Cubs probably deserve even more credit for managing to sign Alex Bregman, and the Red Sox probably deserve even more scorn for letting him slip away.
We already know that, although the Red Sox very much wanted to bring Bregman back, there were disagreements about a no-trade clause, about the length of the deferrals, and the size of the guarantee. Apparently that wasn’t the only set of issues, though, according to Pierzynski:
Alex Bregman became frustrated with the Red Sox because they were unwilling to meet his market after their initial offer, says @AJPierzynski12.The Red Sox then refused to believe Bregman's camp when they told them they had a better offer on the table. pic.twitter.com/cm8SlliYd1
— Foul Territory (@FoulTerritoryTV) January 12, 2026Essentially, Pierzynski says that the sides were negotiating, trying to find the right spot for a deal, and the Red Sox were playing some hardball, when Scott Boras and Alex Bregman indicated they had in hand a better offer that they were willing to accept. The Red Sox responded by saying they didn’t believe it, according to Pierzynski. From there, the Red Sox apparently did come up a little bit, but not nearly enough. Did they still not believe the Cubs offer actually existed?
Again, woooooof.
On the one hand, I suppose I can’t blame the Red Sox entirely, because folks do bluff in these high-stakes negotiations. They play some games with words – what constitutes interest? when is an offer actually a full-on offer? what’s the real value of a contract? etc., etc. – so that maybe no one is outright lying, but everyone knows how much money is at play. There’s a lot to be gained or lost if you navigate the negotiating process ever so carefully. I’m sure that, many times, a team has indeed gotten their guy at their price because they did draw the line and dare an agent to take his client somewhere else.
On the other hand, it kinda sounds like the Red Sox bungled this a bit from the jump, initially under-reading Bregman’s market, and then not getting aggressive enough when things got cooking. Some of that is due to gamesmanship by Boras – he wasn’t going to tell the Red Sox exactly what the Cubs’ offer was or who was offering it, on the hopes that the Red Sox would jump way over the top – but some of it was failing to lock things down when they probably had a clear shot.
For the Cubs’ part, it sounds like they played things just right. Express interest early on so that Bregman’s camp knows you want a seat at the table, but then wait until there’s an opportunity to come in and make an offer that is actually acceptable at a time when Bregman is ready to finalize something. Then, you can create a little timing pressure organically, and maybe pull off the signing before the other interested parties have too long to reconsider their stance (and do more digging about just how real your offer is or isn’t).
Consider all of this a reminder, too, that free agent negotiations aren’t always a simple auction, where everyone knows what everyone else is bidding, and winning simply requires tacking on an extra dollar. All parties are trying to get the best deal they can, understanding that agents want teams to inadvertently bid against themselves, players have real feelings about where they are going to work and live, and teams create many alternative paths for their offseasons that may make This Guy at This Price just as attractive as That Guy at That Price.
Here’s hoping Alex Bregman goes on to make the Red Sox really regret their mistake on this one.
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