MLB Insider: Fact or Fiction? How likely is a Red Sox-Vladimir Guerrero Jr. pairing next winter?

After a report surfaced that Vladimir Guerrero Jr. was likely headed to the Boston Red Sox after the 2025 season, it got me thinking: what actually may be next for the Toronto Blue Jays slugger?

What we know is that Guerrero is one of the premier young players in baseball. The 25-year-old is coming off a season in which he hit .323/.396/.544 with a .940 OPS, 30 home runs and 103 RBI. He’s a cornerstone, franchise-altering player who the struggling Blue Jays have wanted to extend for some time.

But really, the Blue Jays have never come close to extending Guerrero in recent years. Despite their struggles last season, they were adamant about not trading him and holding onto him with the hopes of competing in 2025. The Blue Jays, meanwhile, have not improved the major-league roster for 2025 and appear primed to once again have a disappointing season.

They could have traded Guerrero last July when he had 1.5 years remaining on his contract and gotten a king's ransom, enough to fuel the new era of Blue Jays baseball. Now, if they are out of playoff contention in July, Toronto will only receive a prospect or two for Guerrero if they even make him available in trade talks.

Not moving Guerrero last trade deadline, when his value was immense, was a catastrophic mistake. And they’re seemingly in position to lose him for pennies on the dollar, perhaps just a draft pick if he leaves via free agency.

So what’s next for Guerrero? Let’s dive into it.

For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop between now and the MLB offseason.

Is a Vladimir Guerrero Jr.-Red Sox pairing likely next winter?

Let’s focus specifically on Bob Nightengale’s report, which heavily linked Guerrero to the Boston Red Sox.

Nightengale wrote: “If Guerrero doesn’t receive an extension by spring training, he’ll test free agency, and likely will be wearing a Red Sox uniform in 2026. If Guerrero doesn’t return to the Blue Jays, he would love to be with the Red Sox, friends say, which may be why the Red Sox are hesitant in their pursuit of Alex Bregman.”

I absolutely believe that Guerrero will test free agency. After watching Juan Soto land a record $765 million contract in free agency, he has every reason to head to the open market. But suggesting that the Red Sox are “likely” to land a free agent, especially almost a year away from Guerrero’s free agency, is premature.

I would look for the Red Sox to be involved in the Guerrero sweepstakes. They have every reason to and clearly have the financial wherewithal to sign him, especially after being prominently involved in the Soto bidding. And it would be no surprise whatsoever to see Guerrero seek a contract in the $400-500 million range and ultimately get it, perhaps even more.

But to suggest that the Red Sox are the favorites for Guerrero, at least as of right now, is too strong. It’s simply far too early to tell.