Article: Alex Bregman Should Get an Extension that Keeps Him in Boston Until He Retires

[Alex Mayes]

On Tuesday, June 24, the Boston Globe reported that Alex Bregman is open to discussing a contract extension as the first opt-out of his current contract draws near. That’s huge news considering he was the marquee free agent addition going into the 2025 season. There has been speculation ever since his contract was announced that he would opt out if he had the season that many thought he would have in Boston.

He’s still on the shelf with a quad injury, but he was exceeding expectations before he landed on the injured list. As of his last at-bat, he was slashing .299/.385/.553 with 11 home runs and a .938 OPS. He’s viewed as a leader both on the field and in the clubhouse and plays an excellent third base. Bregman offers everything you could want in a teammate, and it’s obvious that he’s well liked by his peers and coaches.

On Thursday morning, President of Baseball Operations Craig Breslow went on WEEI’s The Greg Hill Show and had this to say regarding the news of a possible extension.

“The specifics of the conversations and the timing of the conversations will remain internal,” Breslow said. “But what I’m very comfortable saying is Alex has been everything we could have asked for both on the field — unfortunately, he’s obviously been hurt and hasn’t been able to impact games on the field — but also in the clubhouse from a leadership standpoint. Not just in the way he’s helped younger players and our staff, but in the ways that he’s helped me and many of us in the front office. And so right now, while we’re focused on doing everything we can to get him back on the field as quickly as possible, when the right time comes to have those conversations, I'm very, very confident that we will."

That sounds like the team is interested in keeping Bregman around for quite a while. While that shouldn’t come as a surprise with the success that Bregman has had in Boston, it’s refreshing to hear that the person in charge of making these decisions is looking forward to having extension talks with the Gold Glove third baseman. After the much-discussed trade of Rafael Devers, the front office has more than enough money on hand to offer Bregman an extension that he won’t be able to so no to. They’d be foolish to let him walk in the offseason, and the best path forward includes him calling Fenway Park home forever. The Red Sox should extend Alex Bregman and keep him in Boston until he retires. 

Bregman’s swing was made for Fenway. He peppers the Green Monster with hard hit balls and sends them both screaming over the wall and into the gaps. Even on the road, he’s an electric hitter that can carry an offense on a down day. Defensively, he’s had a few miscues during his time in Boston so far, but he was settling in when his injury occurred. He has five errors on the season, but he’s already turned 14 double plays. He’s sure-footed on defense and makes heads up plays more often than not. That’s huge, and keeping him on the left side of the infield with Marcelo Mayer for the next few seasons would do nothing but push Mayer to be the best baseball player he could be.

We all know that Bregman is getting older, so his bat and glove won’t play at an elite level for the rest of his career, but that’s okay. As Bregman ages, his leadership becomes his main contribution to the team. If you’ve been on social media after games, you’ll see reports of him working with Marcelo Mayer and Roman Anthony in the clubhouse. He’s visible on the top step of the dugout during every game, often discussing with teammates and coaches about what is happening on the field. He has the championship pedigree to be taken seriously by anyone who hears him speak, but he’s also approachable enough that when the rookies are struggling, they feel comfortable going to him for help. As the Red Sox graduate more rookies from the farm system. Bregman is going to be one of the first people on the team that these players flock to so they can learn exactly what it takes to be a big leaguer, specifically one in Boston. 

Since Alex Bregman is willing to listen to extension offers from the Red Sox, the front office needs to work quickly to get him secured to a long-term deal that allows him to finish his career here in Boston. He has the profile that is made for this ballpark and his leadership skills cannot be replaced easily. The young core has already started to go to him for advice, and the entire fanbase already views him as a leader. Keeping him around until the end of his career — and making him an institution Boston — is the right call for a front office that needs a win right now.

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[TedYazPapiMookie]

Glad the front office might want to pursue a contract extension with Bregman but it's way over the top when "alleged reports" of him working with Mayer and Anthony are suggested without substantiation.  For fans actually watching the games they will see Bregman speaking with most players on the team throughout the game.  He's not mentoring players; he's talking baseball with all his teammates much like he did in Houston.  Suggesting it's targeted mentoring is fake news.  Let's keep the stories real.  Does that mean when Story, Refsnyder, Yoshida or Justin Wilson talk to Bregman they are mentoring him since he's younger?  NO.  It's just two ball players talking baseball.   

Here is yet another example of the preferential treatment afforded both Mayer and Anthony.  Bregman is not specifically set up to mentor the two players, he's there to be a mentor to the young players.  Breslow even pointed that out.  That's all he's doing, just like the other veteran players. 

Also, nothing so far suggests that Mayer will play SS instead of Story during the remainder of Story's contract.  Lots of Mayer fans hope for that but with his questionable defense in the minors and his .208 batting average the change does NOT seem to be imminent.  To suggest playing next to Bregman will bring out the best in Mayer has no basis in fact, it's just a wild conjecture because I believe Mayer will provide his best whether he's at 2B or SS and whether Bregman is directly next to him or not.

The actual focus of the article is good because we need Breslow to extend Bregman.  The fluff part is one fan providing his support for two prospects and Bregman in a non-objective way.  But it is consistent with the bias that exists in the media and with Cora, so it correctly portrays the team group dynamics.

[Alex Mayes]

59 minutes ago, TedYazPapiMookie said:

Glad the front office might want to pursue a contract extension with Bregman but it's way over the top when "alleged reports" of him working with Mayer and Anthony are suggested without substantiation.  For fans actually watching the games they will see Bregman speaking with most players on the team throughout the game.  He's not mentoring players; he's talking baseball with all his teammates much like he did in Houston.  Suggesting it's targeted mentoring is fake news.  Let's keep the stories real.  Does that mean when Story, Refsnyder, Yoshida or Justin Wilson talk to Bregman they are mentoring him since he's younger?  NO.  It's just two ball players talking baseball.   

Here is yet another example of the preferential treatment afforded both Mayer and Anthony.  Bregman is not specifically set up to mentor the two players, he's there to be a mentor to the young players.  Breslow even pointed that out.  That's all he's doing, just like the other veteran players. 

Also, nothing so far suggests that Mayer will play SS instead of Story during the remainder of Story's contract.  Lots of Mayer fans hope for that but with his questionable defense in the minors and his .208 batting average the change does NOT seem to be imminent.  To suggest playing next to Bregman will bring out the best in Mayer has no basis in fact, it's just a wild conjecture because I believe Mayer will provide his best whether he's at 2B or SS and whether Bregman is directly next to him or not.

The actual focus of the article is good because we need Breslow to extend Bregman.  The fluff part is one fan providing his support for two prospects and Bregman in a non-objective way.  But it is consistent with the bias that exists in the media and with Cora, so it correctly portrays the team group dynamics.

The linked tweet is literally Chris Cotillo from inside the clubhouse talking about how Bregman was working with Marcelo and Roman. You know, mentoring them. The other names you mentioned were not in the piece because they are not part of the future core of this team. 

[harmony]

Alex Bregman is accustomed to playing for winning teams, experiencing his only losing campaign in the shortened 2020 season. Since Bregman entered the league in 2016, the Astros have posted MLB's second-best record, advancing to the World Series four times, winning twice.

Bregman may listen to the Red Sox but how interested should Bregman be in an franchise that is currently struggling to post its first winning season since 2021? Does this year's Sox drama increase or decrease Bregman's interest in a long-term commitment with the Red Sox? How likely is a Scott Boras client to sign an extension in season?

[mvp 78]

I agree with the premise of keeping Bregman around for the remainder of his career depending on the amount of his contract. I think he's hitting above his weight right now (our expectations should be closer to an 800 OPS at best), but seems to be a great fit for a young clubhouse. My only concern is that this quad injury is a similar injury to the one he had in '21 and he's at the age where this may just start happening more and more. 

[mvp 78]

2 minutes ago, harmony said:

How likely is a Scott Boras client to sign an extension in season?

Boras is paid to do what his clients ask him to do. 

For example, Varitek took less money to stay with the Red Sox and was a Boras client. If Bregman wants to stay here, Boras can work it out. 

[Maxbialystock]

46 minutes ago, mvp 78 said:

I agree with the premise of keeping Bregman around for the remainder of his career depending on the amount of his contract. I think he's hitting above his weight right now (our expectations should be closer to an 800 OPS at best), but seems to be a great fit for a young clubhouse. My only concern is that this quad injury is a similar injury to the one he had in '21 and he's at the age where this may just start happening more and more. 

Agree.  The 2d quad injury is worrisome.  So is the pitching.  

It was a big gamble to offer Bregman $120M for 3 years. 

Moreover, as great as Bregman's first 2 months were, the Sox were at 26-26 after the game in which he was injured.   By then, I hasten to add, we already knew how good Crochet, Chapman, and Narvaez are.   Even had Raffy stayed was there any guarantee the Sox would have improved on .500?  I don't think so.  The Sox went over .500 because of that 6 game winning streak in which opposing teams scored a total of 8 runs.   They didn't need Bregman--or Devers, for that matter.   

 

 

 

 

 

 

 

[TedYazPapiMookie]

9 hours ago, Alex Mayes said:

The linked tweet is literally Chris Cotillo from inside the clubhouse talking about how Bregman was working with Marcelo and Roman. You know, mentoring them. The other names you mentioned were not in the piece because they are not part of the future core of this team. 

Right.  Bregman is not mentoring anyone else except the two privileged guys?  Find that hard to believe and the fact that you didn't even read the response tells me everything I need to know.  The "other names" in my response were the only players older than Bregman not prospects so your answer clearly didn't address what I wrote.  You read a link from Cotillo out of context and mentioned it.  Got it.  Don't worry I won't question you again knowing you don't really read the comments and put thought into your responses.  I get it.

[Alex Mayes]

9 hours ago, mvp 78 said:

I agree with the premise of keeping Bregman around for the remainder of his career depending on the amount of his contract. I think he's hitting above his weight right now (our expectations should be closer to an 800 OPS at best), but seems to be a great fit for a young clubhouse. My only concern is that this quad injury is a similar injury to the one he had in '21 and he's at the age where this may just start happening more and more. 

The second quad injury worries me as well, I just didn't highlight that here. We talked about that on the episode of the podcast right after he was injured. Them pushing his return date back to likely after the All-Star break is a bit telling too. 

[moonslav59]

He needs to be back, next year. Anything beyond is great.

Get it done!

[SPLENDIDSPLINTER]

If the Sox are out of the PO hunt in late July, which seems likely, I believe Bregman gets traded. IMHO, they're gonna rebuild around the youngsters with their main goal set on finding starting pitching.

Eventually, this will be a good team again, but it ain't gonna be this year. Stay tuned.

[moonslav59]

36 minutes ago, SPLENDIDSPLINTER said:

If the Sox are out of the PO hunt in late July, which seems likely, I believe Bregman gets traded. IMHO, they're gonna rebuild around the youngsters with their main goal set on finding starting pitching.

Eventually, this will be a good team again, but it ain't gonna be this year. Stay tuned.

What's the odds we sit Bregman down and talk about how much we want him back in 2026, then trade him and bring him back? (It wouldn't really be tinkering, since he's under contract with him, now.)

He could still be a piece to build a young team around starting in 2026. It's not like our best young players are in single A.

[cp176]

I wonder what Bergman is thinking.  Outside of being incredibly well paid, why would he want to stay here?

[jad]

I just read a post above claiming that the RS did not need either Devers or Bregman.   Was that authored by JH's yacht designer?

[Alex Mayes]

6 hours ago, moonslav59 said:

What's the odds we sit Bregman down and talk about how much we want him back in 2026, then trade him and bring him back? (It wouldn't really be tinkering, since he's under contract with him, now.)

He could still be a piece to build a young team around starting in 2026. It's not like our best young players are in single A.

I had this same thought. Sit down with him, agree to terms, and trade him because he wants to win. Is. Then he opts out and comes back on a long term deal. I just don’t think the front office is savvy enough to actually pull it off. Maybe if they let Theo and only Theo handle the conversation. 

[Bellhorn04]

1 hour ago, jad said:

I just read a post above claiming that the RS did not need either Devers or Bregman.   Was that authored by JH's yacht designer?

That was Max.  To be fair he was only referring to a stretch of games we won because of our pitching.  Beyond that I'll leave it to him to explain.

[Bellhorn04]

47 minutes ago, Alex Mayes said:

I had this same thought. Sit down with him, agree to terms, and trade him because he wants to win. Is. Then he opts out and comes back on a long term deal. I just don’t think the front office is savvy enough to actually pull it off. Maybe if they let Theo and only Theo handle the conversation. 

Sounds good in theory but that's not a binding agreement because it can't be.  It would basically be worth no more than telling him we'd love to have you back.  Once he's traded you lose any possible control of the situation.  If you really want him back you offer an extension.

[Alex Mayes]

3 hours ago, Bellhorn04 said:

Sounds good in theory but that's not a binding agreement because it can't be.  It would basically be worth no more than telling him we'd love to have you back.  Once he's traded you lose any possible control of the situation.  If you really want him back you offer an extension.

Absolutely. It’s a hope and a prayer for sure. 

[moonslav59]

6 hours ago, cp176 said:

I wonder what Bergman is thinking.  Outside of being incredibly well paid, why would he want to stay here?

Maybe he loves the park?

Career: 1.046 at Fenway

.846 HOU

[notin]

On 6/27/2025 at 9:37 AM, mvp 78 said:

I agree with the premise of keeping Bregman around for the remainder of his career depending on the amount of his contract. I think he's hitting above his weight right now (our expectations should be closer to an 800 OPS at best), but seems to be a great fit for a young clubhouse. My only concern is that this quad injury is a similar injury to the one he had in '21 and he's at the age where this may just start happening more and more. 

Depends on the contract.  He’s a 4-5 fWAR player but at 31, that’s not likely to last long…

[moonslav59]

18 minutes ago, notin said:

Depends on the contract.  He’s a 4-5 fWAR player but at 31, that’s not likely to last long…

That's why I said I just hope he comes back next year and maybe a few years afterwards.

I'd be willing to go 4-5, just so we get him for the first 2-3 years.

[Maxbialystock]

8 minutes ago, moonslav59 said:

That's why I said I just hope he comes back next year and maybe a few years afterwards.

I'd be willing to go 4-5, just so we get him for the first 2-3 years.

You're probably right, but not if the quad thing returns.  Except for that, Bregman is perfect for the Sox.  

[moonslav59]

18 minutes ago, Maxbialystock said:

You're probably right, but not if the quad thing returns.  Except for that, Bregman is perfect for the Sox.  

Injury does worry me, but to me, Bregman is a proven star on O and D and helps his teammates be better.

Every 4-5 year deal is a big risk.

[Kimmi]

I love having Bregman on the team, and I hope he decides not to opt out.  However, he is 31 years old.  While he's currently still playing at a high level, I'm not sure how wise an extension would be.  For me, the saving grace of his current contract is that it is only for 3 years.  I don't want to turn that into anything longer.