Latest Vladimir Guerrero Jr. rumors could create all-new Yankees nightmare

After being spurned by one of the biggest fish ever to hit free agency, one who had tread the hallowed grounds in the Bronx and hung with the legends out in Monument Park before saying, "Thanks, but no thanks", the Yankees rebounded and everything seemed to be falling into place this offseason.

They added another ace to the deck in Max Fried. They traded for Cody Bellinger, whose sweet lefty swing is tailor-made for the Bronx. They added arguably the most dominant closer in baseball. Most importantly, they filled their hole at first base with a former MVP who is primed for a bounce-back campaign and it only cost a one-year commitment, priming themselves for a do-over for the next "generational" free agent.

That leaves the possibility open for Brian Cashman and company to go chase the next generational star to hit the market after the 2025 season, and given the Blue Jays' ineptitude, it certainly looks like that chance will come to fruition.

The stars seem to be aligning for Vladimir Guerrero Jr. to hit the open market and just like the famous standoff scene between Mr. Orange, Mr. Pink, and Mr. Blonde at the climax of Reservoir Dogs an encore of the Soto chase appears to be shaping up between the usual suspects.

The longer the Mets go without reuniting with Pete Alonso, the more likely they are to find a stopgap and enter the Guerrero chase next offseason. Though he has previously said he'd never sign with the Yankees, not even if he were "dead," he did back off of that stance during last year's trade deadline.

But the apple of Guerrero's eye might be something even more terrifying for the Yankees than losing another big fish to their crosstown rival. No, it might not be the little brother Mets ready to rain on any future pinstripe parades down the Canyon of Heroes, but rather a dormant beast to the north that should send trembles down our collective spines. That is, Vladdy Jr. might love to become a Boston Red Sox.

According to Bob Nightengale, the Red Sox are lurking for Guerrero Jr., which may explain their hesitance to commit to Alex Bregman. Nightengale went so far as to say that Guerrero Jr.'s friends believe he prefers Boston out of all options. Now, they'll just have to accede to his rumored $450 million request (a worthwhile sum to ruin the Yankees in the process).

Are the Yankees no longer a premier free agent destination? Will they really see Vladimir Guerrero Jr. choose the Boston Red Sox?

Pride, power, and pinstripes. Those three things, along with mountains of cash, used to be the key selling point for the biggest of stars to desire playing in the Bronx. After all, this is the winningest franchise in professional sports, with over 100 years of greatness immortalized within the confines of Monument Park.

With few notable exceptions, no one has been able to resist the Yankees' siren song, yet in recent years, it seems as if Brian Cashman, Randy Levine, and Hal Steinbrenner are singing off-key.

Sure, there have been big deals signed with the Bronx Bombers in the not-so-distant past. Max Fried just put pen to paper on a massive contract, for instance. But when was the last time the Yankees came away with a prize that was the envy of all, to the point where the outcome was essentially predetermined? That would be five years ago when Gerrit Cole signed a record-breaking deal to lead the Yankees staff.

Back when Cole was a free agent, it was a foregone conclusion that he'd end up in pinstripes. However, as Juan Soto has shown us, and the smoke around Vladdy Jr. indicates, that is no longer the reality.

Such is the real nightmare for Yankees fans. The pinstripe pride has lost some of its luster, and bottomless pockets might not be enough to make up for it. Maybe we can blame years of "fiscal responsibility." Maybe we should blame Cashman's smug way of trying to outsmart the market at every turn. In the case of Guerrero, maybe we should blame ol' George for preferring Gary Sheffield over his Hall of Fame father.

Whatever the case may be, there's plenty of time to go before the next big free-agent showdown. Maybe the Blue Jays get their act together and finally get someone to take their money. Or maybe they fall out of the race early and move Guerrero ahead of the trade deadline. But should he hit the open market, it looks like a three-horse race for his services, and for the first time in a long time, the Yankees are the longshot.