Should Boston Pilfer A Division Rival to Replace Alex Bregman in Free Agency?

[Jordan Leandre]

With how the 2025 season unfolded, it's hard to picture any Boston Red Sox team for the remainder of the 2020s not having third baseman Alex Bregman on it.

Even with the injury and subsequent struggles upon returning, the All-Star slashed .273/.360/.462 with a 125 wRC+ and 3.5 fWAR in 114 games. He also had a .462 on-base percentage in the team's three-game Wild Card series against the New York Yankees and hit an RBI double to seal Game 1.

He made the decision to opt out of his current contract earlier this month, at least temporarily removing himself from the equation in Boston. Therefore, for the second offseason in a row, the team covets a middle-of-the-order righty bat... or two. Many assume (hope?) that the team will add a righty bopper in addition to Bregman. That pairing may have worked on the field, and the group loved him behind the scenes, but does it really make sense for the Red Sox to commit to him for six additional years on top of adding another high-priced player to the mix?

The free agent market for impact right-handed bats is top-heavy, meaning the market cultivated by each player may need to act more desperate to land said player. Even when factoring in the trade market, there's just not a lot of noise surrounding impact righty hitters right now. That said, Jim Bowden of The Athletic ran a list of contract predictions. In his predictions, he has Bregman receiving a six-year deal worth $182 million -- a $30.3 million average annual value.

That's the same contract he predicted New York Mets first baseman Pete Alonso gets in free agency. Both would be risks at their age, yes, but the upside is also unquestionable. Yet, the contract that caught my attention was that for Toronto Blue Jays infielder Bo Bichette.

Bowden predicts Bichette will get seven years at $189 million total value ($27 mil AAV). Despite 2026 being his age-28 season, and coming off a 2025 in which he was better than Bregman at the plate, he has to get a full extra year to obtain just $7 million in total value. It's worth mentioning that these are simply predictions from Bowden (who is far from the most infallible source), so it's hardly a perfect indicator of the contract any of these players receive. For reference, ESPN's Jeff Passan predicted in September Bichette would sign a deal in the ballpark of what fellow shortstops Trea Turner and Xander Bogaerts got.

Regardless, if the final contracts are close between Bregman and Bichette, and signing both is unfeasible, the Red Sox should target the services of Bichette.

For starters, there's the aging curve of the two players. Bregman is already 32 years old and coming off of a season in which he dealt with a significant quad injury. Assuming it heals with rest, that shouldn't impact his play moving forward. but it serves as a reminder that he's getting older and with that comes injuries. On the other hand, Bichette will be 28 years old next season, meaning he's still got the prime of his career ahead of him. Not only that, but he's become a lock for 60 or so extra-base hits a year. Though his walk numbers aren't spectacular, he hits the ball hard and doesn't strike out. Yes, some BABIP luck is required since he's not a 30-plus-homer guy. But he only outperformed his expected batting average by four points in 2025 -- the dude mashes.

That said, shortstop isn't the position Bichette sticks at long term, if one were to guess. Perhaps that's the reason Bowden is so low on his contract value. Calling him a butcher at the position feels harsh, but apropos to his defensive production. In 2025, he posted -13 DRS and -12 OAA, bringing his career totals to -19 and -32, respectively. Moving to second base seems like the obvious solution. In fact, Bichette is already playing there in the World Series for Toronto, albeit mostly due to physical limitations caused by a knee injury. While still not moving well, he's made some nice plays so far in this series at the position.

There's one issue with signing Bichette to play second base, however. The Red Sox theoretically have two already on the roster, with the other playing short, between Trevor Story and Marcelo Mayer. As a result, they have three middle infielders and no third baseman to replace Bregman.

The logical solution would be to situate Mayer at third base. However, the team must also navigate the possibility of Story's defensive regression being permanent and not some one-off. Thus, I've begun wondering about the upside of sticking Story at third base for the final two years of his contract.

It seems extreme, seeing as there are clear limitations to Story's arm. Not only that, but he posted 10 OAA in 2022 at second base. That said, the veteran infielder posted zero OAA moving to his left and -2 ranging in—it was to his right that really tanked his defensive metrics.

With third base not being the rangiest position on the field, it could do him some good not having to cover as much ground, which wouldn't be the case at the keystone whether he's playing alongside Triston Casas, Nathaniel Lowe or Pete Alonso in 2026. The Red Sox wouldn't be the first team to spam shortstops with a hypothetical Bichette signing. The San Diego Padres, as recent as 2024, had done the same. Their entire infield was comprised of shortstops: Bogaerts, Ha-Seong Kim, Manny Machado, and Jake Cronenworth.

Deploying three shortstops and an offensive-minded first baseman could give the Red Sox a much more dynamic infield while not suffering at the plate, and Bichette's cleaner fit with the timeline of their current core could make him a de facto leader going forward, much like how George Springer has taken these current Blue Jays under his wing.

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[5GoldGlovesOF,75]

Boras will pilfer as much time as possible before letting Bregman sign anywhere -- which basically pilfers all the payroll plans for other upgrades.

Overwhelm Bichette with a swift offer and then focus all winter on trading for a starting pitcher and a first baseman with pop.

[notin]

That 2024 Padres outfield (Profar, Merrill, Tatis) was entirely comprised of shortstops as well.

The Sox might just have to live with Story’s declining defense.  It is only two years and tolerating decline is part of signing free agents…

[Hitch]

15 minutes ago, notin said:

That 2024 Padres outfield (Profar, Merrill, Tatis) was entirely comprised of shortstops as well.

The Sox might just have to live with Story’s declining defense.  It is only two years and tolerating decline is part of signing free agents…

Agreed. I didn't realise Bichette was still so young. I'd be more than okay with him at 2nd and Story/Mayer manning 3rd/SS between them, as long as the contract is reasonable. 

This team could do with more hitters that put the ball in play, too, as long as we get another masher (or 2 preferably), but how we'd do all that with the payroll I don't know. 

[Hugh2]

Bichette is a good 4 years younger than Bregman, he might be a lot better over the next 6 years. 

[Old Red]

1 minute ago, Hugh2 said:

Bichette is a good 4 years younger than Bregman, he might be a lot better over the next 6 years. 

Agree on Bichette, but I don’t think the Red Sox want to go that long on a contract.

[mvp 78]

9 minutes ago, Hugh2 said:

Bichette is a good 4 years younger than Bregman, he might be a lot better over the next 6 years. 

Might be, but I don't like his glove and the Sox are saying they are trying to improve D.

[Hitch]

6 minutes ago, mvp 78 said:

Might be, but I don't like his glove and the Sox are saying they are trying to improve D.

Their problem is, they want to improve D and get more power into the line up. Two things that don't often go hand in hand.

I think playing him at 2nd would see an uptick in his D. How much is questionable, however. 

His lack of strike outs is appealing.

[Hugh2]

8 minutes ago, mvp 78 said:

Might be, but I don't like his glove and the Sox are saying they are trying to improve D.

I know this is a lazy way to look at things, but I assume a s***** short stop can play at least average defense everywhere else minus catcher.  If I'm signing Bichette it's to play 2nd. 

[Hugh2]

18 minutes ago, Old Red said:

Agree on Bichette, but I don’t think the Red Sox want to go that long on a contract.

Well we can wish right?

As the great Willie (Billy Bob Thorton in Bad Santa) once said "s*** in one hand and wish in the other and see which one fills up first). 

I'm going to dream a little this offseason and hope the ghost of john henrys spending past comes back this holiday season. But I can't help but think we are getting Arenado instead this offseason. 

[notin]

48 minutes ago, Hitch said:

Agreed. I didn't realise Bichette was still so young. I'd be more than okay with him at 2nd and Story/Mayer manning 3rd/SS between them, as long as the contract is reasonable. 

This team could do with more hitters that put the ball in play, too, as long as we get another masher (or 2 preferably), but how we'd do all that with the payroll I don't know. 

That’s why I’ve been suggesting/advocating/yelling into the void for a non-1b slugger like Marte or Bichette or Bregman (my prediction but ultimately last choice on this list).  It will be easier to get a discount mashing 1b/DH type than a discount mashing infielder.  Some like Hoskins.  I prefer Bell.  Both will be significantly cheaper than Alonso, who will in turn limit what can be spent on the other infielder.

Now if the Sox do get Alonso, my hope would be to trade for non-mashing but hard-hitting Brendan Donovan at 2b, as he was #3(I think?) on the MLBTR trade candidate list….

[notin]

27 minutes ago, Hugh2 said:

Bichette is a good 4 years younger than Bregman, he might be a lot better over the next 6 years. 

I would bet Bichette gets more than six years…

[Hitch]

2 minutes ago, notin said:

That’s why I’ve been suggesting/advocating/yelling into the void for a non-1b slugger like Marte or Bichette or Bregman (my prediction but ultimately last choice on this list).  It will be easier to get a discount mashing 1b/DH type than a discount mashing infielder.  Some like Hoskins.  I prefer Bell.  Both will be significantly cheaper than Alonso, who will in turn limit what can be spent on the other infielder.

Now if the Sox do get Alonso, my hope would be to trade for non-mashing but hard-hitting Brendan Donovan at 2b, as he was #3(I think?) on the MLBTR trade candidate list….

I wouldn't have had Bichette in the slugger category, but looking at his numbers he has some pop to go along with his average. I'm coming more and more around to this idea if we can get him at a good deal. But...

 

- The Athletic's Jim Bowden projects him to sign for $189 million.

- NBC Sports' Matthew Pouliot recently projected Bichette would sign a massive eight-year, $216 million deal in free agency.

- Baseball America projects Bichette to sign an eight-year, $240 million

 

...seeing as Bowden is a f'kin idiot, I'd say we're looking at somewhere between the last two contracts, which is pulling the collar away from the neck territory. 

[Hitch]

 

[Hugh2]

1 hour ago, notin said:

I would bet Bichette gets more than six years…

Yeah, he will be fighting for 8 I think and he might get it.  I wouldn't mind overpaying to have him for 6.  I'd at least offer 225/6

[mvp 78]

1 hour ago, Hugh2 said:

I know this is a lazy way to look at things, but I assume a s***** short stop can play at least average defense everywhere else minus catcher.  If I'm signing Bichette it's to play 2nd. 

That's a very lazy way to look at things. I think he'd be a below average 2b TBH. The move off of SS also greatly affects his value. 

[mvp 78]

4 minutes ago, Hugh2 said:

Yeah, he will be fighting for 8 I think and he might get it.  I wouldn't mind overpaying to have him for 6.  I'd at least offer 225/6

Oh hell no. 

[notin]

3 minutes ago, Hugh2 said:

Yeah, he will be fighting for 8 I think and he might get it.  I wouldn't mind overpaying to have him for 6.  I'd at least offer 225/6

So $37.5mill AAV?  Give him too much per year and Kutter Crawford becomes the best #2 that the Sox will pay for…

[mvp 78]

6 minutes ago, notin said:

So $37.5mill AAV?  Give him too much per year and Kutter Crawford becomes the best #2 that the Sox will pay for…

Silly season has commenced. 

[mvp 78]

Bichette hit his Fenway HR's off:

Eovaldi

ERod

Pivetta (2) - '21 version

Kluber 

Webber

[notin]

4 minutes ago, mvp 78 said:

Bichette hit his Fenway HR's off:

Eovaldi

ERod

Pivetta (2) - '21 version

Kluber 

Webber

Who is that Webber chap?

[moonslav59]

1 hour ago, mvp 78 said:

Might be, but I don't like his glove and the Sox are saying they are trying to improve D.

Agreed, and only his age progression chart looks better than Bregman on offense. It's a sideway move on offense and a step down on D, especially if he demands SS. (Even if he plays 2B, it means Story does not move there, so no big gain, anyway.)

[Hugh2]

We do this EVERY YEAR, and you guys always undersell what these free agents are going to make.  

Bichette WILL be paid over 200 million.  I'm overpaying to get him off the books at 33 and not paying for him into his late 30's.  If I'm paying him an extra 5-7 million a year to do that....great. 

[Hugh2]

50 minutes ago, mvp 78 said:

That's a very lazy way to look at things. I think he'd be a below average 2b TBH. The move off of SS also greatly affects his value. 

agree, but isn't just as lazy to say you just assume he'll be a bad 2nd? his defense has actually gone up/down over the last few years at SS with some years grading out average to better.  Via statcast, he was in the 51% for fielding run value (average) in 2024, he was literally average a year earlier.  Why shouldn't we assume he will be better at 2nd? that's a pretty decent assumption people make because it's typically what we see.  

If he's a bad defender then playing below average D at SS isn't inflating his value much if at all. 

[Hugh2]

52 minutes ago, notin said:

So $37.5mill AAV?  Give him too much per year and Kutter Crawford becomes the best #2 that the Sox will pay for…

I mean, do you have a better ideal for improving the lineup?

 

[notin]

8 minutes ago, Hugh2 said:

I mean, do you have a better ideal for improving the lineup?

 

I’ve literally posted dozens of them.  I rarely (re: never) attach dollar values, but I do suggest trades that often are at a minimum “fair” on BTV.  (I also post ones where Boston overpays, but never ones where the other team does.)

[Hugh2]

6 minutes ago, notin said:

I’ve literally posted dozens of them.  I rarely (re: never) attach dollar values, but I do suggest trades that often are at a minimum “fair” on BTV.  (I also post ones where Boston overpays, but never ones where the other team does.)

I don't claim to know it all, but one thing I see time and time and time again and every year, repeat, without fail, is all of us severaly underestimating how much guys get paid. 

The reality is, you either want to pay the price of admission......or you do not.

I have no idea what the price of Bichette would be, I'm speculating, so it's a bit interesting the price tag is centerpiece of this conversation but I do know two things to be true. 

- Bichette is going to get paid, likely more than what anyone in here is going to predict. 

- Bichette, like any free agent, would have to be paid more per annum to entice them to sign for less years.  

[mvp 78]

28 minutes ago, Hugh2 said:

We do this EVERY YEAR, and you guys always undersell what these free agents are going to make.  

Bichette WILL be paid over 200 million.  I'm overpaying to get him off the books at 33 and not paying for him into his late 30's.  If I'm paying him an extra 5-7 million a year to do that....great. 

I'm stating what I'd pay him, not what he'll go for. 37M AAV is not worth it for Bo. He was terrible last season and is moving off of SS. 

[mvp 78]

3 minutes ago, Hugh2 said:

I don't claim to know it all, but one thing I see time and time and time again and every year, repeat, without fail, is all of us severaly underestimating how much guys get paid. 

The reality is, you either want to pay the price of admission......or you do not. 

I'm not paying for Bo. 

[notin]

4 minutes ago, Hugh2 said:

I don't claim to know it all, but one thing I see time and time and time again and every year, repeat, without fail, is all of us severaly underestimating how much guys get paid. 

The reality is, you either want to pay the price of admission......or you do not.

I have no idea what the price of Bichette would be, I'm speculating, so it's a bit interesting the price tag is centerpiece of this conversation but I do know two things to be true. 

- Bichette is going to get paid, likely more than what anyone in here is going to predict. 

- Bichette, like any free agent, would have to be paid more per annum to entice them to sign for less years.  

That’s why I don’t attach money.  I’m either going to underestimate or overcompensate.  There is no third option.

Trades?  BTV gives me their interpretation of “fair,” and the deals probably are fair.  That doesn’t mean other teams like them.  Sometimes teams don’t want to make fair trades and want to rip you off.  Not much I can do to guess that.