First up, we can’t ignore the New York Mets. Steve Cohen has a limitless supply of money at his disposal and his front office has already “checked in” on Guerrero. Sure, Pete Alonso has been handed first base for this year and probably next given that he has a player option for 2026. But there’s still room as a DH.

Next, there’s the Boston Red Sox. After whiffing on Juan Soto, the Red Sox still have an abundant supply of cash to deal from. It also helps that Guerrero has already voiced a desire to play in Beantown.

And last but not least … the Yankees? Wait a minute; this can’t be right. In past years, Guerrero has disparaged the Yankees most notably saying that he would “never sign with the Yankees — not even dead.”

Since then, he has softened his tone, but it still doesn’t quite seem like Guerrero is eager to don Yankees’ pinstripes and play in the Bronx. Despite Guerrero’s animus towards the Yankees, one former GM has already predicted such an outcome. But while predictions are often unreliable, this one might have just become more relevant. This has nothing to do with the Yankees announcing they’re ready to engage in a bidding war or another unrelated prediction, rather it is something Guerrero did himself.

Vladimir Guerrero Jr. placed a like on an Instagram post of himself wearing a Yankee uniform

In a shocking development, Guerrero has seemingly liked an Instagram post featuring himself photoshopped into a Yankee jersey. Could this be a nod of approval to his longtime AL East rival
(or perhaps an accidental click thinking it was a dislike button)?

Indeed, it seems as though Guerrero has stoked every Yankee fan’s dream of a Vladdy-Judge one-two punch bringing punishment to opposing pitchers. But, while it may be an encouraging sign, let’s hold off on penciling his name on next year’s Yankee roster.

Every great free agency chase begins with giving teams the run-around. Signaling you’ll play for anyone is usually a leverage play to get what you want. If Guerrero were to flat-out decline to entertain offers from the Yankees, his leverage in any free agency discussions would be much weaker. It would be a grand mistake to exclude a rich bidder like the Yankees thus negating their ability to run up the price.

So, is Guerrero truly anticipating a career with the Yanks? Most likely not. But in the end, like with most superstar free agency pursuits, it will likely come down to the cash on the table. Will Hal Steinbrenner offer Guerrero enough to forget his baleful disposition towards the Yankees? We won’t know that until next winter. But there’s no need to worry. Brian Cashman has already set his eyes on a suitable backup plan.