Jeff Passan connecting Yankees to Alex Bregman makes trade deadline sting even more

Alex Bregman of the New York Yankees ... wow ... it really could happen this offseason, if the Boston Red Sox don't respond kindly to his forthcoming contract opt-out. And it also really could've happened last offseason, when he was on the open market after a down year! Instead, the Yankees let him become Boston's de facto captain and (most of) the rest is history.

This offseason, it appears the Yankees will get a shot at sloppy seconds, as ESPN's Jeff Passan confirmed on Thursday that Bregman intends to trigger an opt out and test the market, seeking more security than the two years theoretically remaining on his Boston deal. Alex Bregman: Great Clubhouse Guy, Better Money Guy.

This isn't the first time the Yankees have been connected to Bregman in the past calendar year. The first time, it was mostly wish-casting, though, from Yankee fans who wanted somebody to shake up their clubhouse, as well as Bryan Hoch calling their interest "real" after losing Juan Soto. It is, however, the first time they've been connected to his market after trading for Ryan McMahon at the 2025 deadline, a relatively hefty deal that carries him through 2027.

No offense to McMahon, who's been a slick glove and a professional at-bat in pinstripes (if, more often than not, an unsuccessful one). But something tells us that the Phillies and Tigers — as well as the Red Sox, who saved that Devers money — are all more likely suitors for Bregman than the Yankees this offseason.

New York could've added a rental third baseman instead of McMahon, or a cheaper, controllable piece. They did not. He's their guy now.

Yankees Rumors: An Alex Bregman landing spot, despite Ryan McMahon's contract? Eh?

Of course, the cherry on top is that whichever team signs Bregman this offseason (Red Sox or otherwise) is the one most likely to get stuck with a lemon. His resurgence in the Fenway Park bandbox this season has been exceptional, and it's definitely going to work for ... three years or so, otherwise known as the duration of the first opt-out-packed Sox contract.

If Bregman wants seven years this time around and someone gives it to him, that's where it goes sour. Boston has a chance to get the very best of him and move on, or continue the relationship and swallow their tongue on the back half of the contract.

It's not going to happen, but it'd be very "Yankees" to let Boston get the short-term win, then absorb the long-term loss instead.