Inside The Red Sox

Red Sox's Possible No. 1 Free-Agent Target Hints At Lofty Contract Expectations

How high will the Red Sox be willing to push their offer?
Sep 25, 2024; Toronto, Ontario, CAN;  Toronto Blue Jays first baseman Vladimir Guerrero Jr. (27) hits a double as  Boston Red Sox pitcher Richard Pitts (80) looks on in the fourth inning at Rogers Centre. Mandatory Credit: Dan Hamilton-Imagn Images
Sep 25, 2024; Toronto, Ontario, CAN; Toronto Blue Jays first baseman Vladimir Guerrero Jr. (27) hits a double as Boston Red Sox pitcher Richard Pitts (80) looks on in the fourth inning at Rogers Centre. Mandatory Credit: Dan Hamilton-Imagn Images | Dan Hamilton-Imagn Images

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The Boston Red Sox proved this past offseason that they're willing to spend big once again to give themselves a shot at a championship. Come November, they'll get a chance to prove just how big.

Current Toronto Blue Jays first baseman Vladimir Guerrero Jr. will hit free agency after the coming season, having failed to reach an extension with the Red Sox's division rival by his self-imposed deadline of mid-February.

There's been a lot of smoke tying the Red Sox to Guerrero, and for good reason. He's one of the best right-handed batters in the sport, which would fill a hole in the middle of the Boston lineup, and he's expressed that he'd "love" to play for Boston if a Blue Jays reunion doesn't work out.

The Red Sox tried to get involved for superstar outfielder Juan Soto this offseason, but ended up losing him to the New York Mets for a 15-year, $765 million contract. Though Guerrero isn't quite the player Soto is, it will certainly take a large sum to land him as well.

How much? Guerrero gave the Red Sox--and other interested parties--a pretty good idea with his comments on Thursday.

“It’s much less than Soto. We’re talking about many fewer millions than Soto, more than a hundred million less,” Guerrero told ESPN’s Enrique Rojas and Ernesto Jerez. ”It was the same number of years, but it didn’t reach ($600 million). The last number we gave them as a counteroffer didn’t reach 600.

“I know the business. I lowered the salary demands a bit, but I also lowered the number of years… I’m looking for 14 (years). I would like 14, 15, even 20 if they give them to me, but doing it the right way.”

The largest contract the Red Sox have ever given out was the recent 10-year, $313.5 million extension for third baseman Rafael Devers. Going to a number nearly twice that much for a slugger with similar career numbers to Devers could certainly be a stretch.

But free agency isn't just about sticking to your own track record. Guerrero is an undeniably good fit for the Red Sox, even if it means moving some pieces around to fit him, Devers, Alex Bregman, and Triston Casas all in the same lineup.

One thing that seems obvious, though: If Boston isn't willing to give Guerrero the 14 or 15 years he wants, some other team almost definitely will.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org