Back in late June, Alex Bregman’s agent Scott Boras said that his client was “always open to any conversation” about a longer-term agreement with the Red Sox. This created the impression that an in-season extension between the two sides was perhaps possible, though Bregman seemingly put an end to that idea when speaking with the Boston Globe’s Tim Healey today. While Bregman is “obviously…open to talking” at season’s end, the third baseman stressed that “for the next few months, I’m just really focused on the baseball. I’m just focused on trying to do what I can to help this team win and get into the playoffs. I feel like that’s where my head and mind need to be.”
Most players adopt this same stance with extension negotiations, preferring to have any deals finalized either prior to Opening Day or just after (if talks were almost but not quite completed by the first game). That said, there have also been plenty of in-season extensions over the years, as naturally each player has a different set of circumstances that can impact a long-term deal. For instance, the Red Sox completed a major extension just a few days ago with Roman Anthony, as the rookie sensation locked in the first fortune of his pro career by signing an eight-year contract that will pay him at least $130MM.
It is more rare to see an established veteran sign a new contract so close to free agency, so it isn’t surprising to see Bregman choose to put negotiations aside until Boston’s season (and what he hopes is a deep playoff run) is complete. Bregman signed a three-year, $120MM free agent deal with the Sox last winter that contains opt-out clauses after each of the first two seasons. That means Bregman can bank his $35MM salary from 2025 and leave the remaining money on the table in order to pursue a richer and longer-term commitment in another trip to the open market this offseason.
Bregman’s first season in Beantown was interrupted by a quad strain that kept him out of action for just shy of seven weeks. That significant absence notwithstanding, there is little doubt Bregman will indeed trigger his opt-out clause, as he is hitting .298/.380/.531 with 14 homers over 313 plate appearances in a Red Sox uniform. This translates to a 148 wRC+ that would be Bregman’s highest since his 167 wRC+ during the 2019 season with the Astros — Bregman finished second in AL MVP voting during this high point of his outstanding career.
Red Sox chief baseball officer Craig Breslow raved about Bregman during a radio interview in June, describing the third baseman as “everything we could have asked for both 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.” This praise of Bregman has been echoed by teammates and manager Alex Cora, leaving no doubt of Bregman’s quick impact on a young Red Sox team that is in the thick of the postseason race.
It would certainly seem that the Sox are willing to offer Bregman a lucrative deal that tacks a few more years onto his current contract (or overwrites it entirely) in order to get him to forego his opt-out decision. Bregman and Boras went into the 2024-25 offseason reportedly looking to land a $200MM guarantee, so speculatively speaking, perhaps a five-year, $165MM extension might be enough to get things done.
Such a deal would commit Bregman to the Red Sox through his age-36 season, give him the overall $200MM payday he was seeking in the first place, and perhaps get more money into his bank account a little sooner, depending on how this hypothetical contract is structured. Bregman’s current deal contains $60MM in deferred money, so Bregman is only receiving $20MM of his $35MM salary for 2025. Then again, Bregman could be open to deferrals since such an arrangement lowers the luxury tax hit of his contract, thus giving the Red Sox more flexibility in spending more on acquisitions or in locking up other players to extensions.
There are some parallels to Matt Chapman’s situation here, even though Bregman apparently won’t be following his fellow Boras Corporation client in signing an extension before the season is over. Chapman signed a three-year, $54MM deal with the Giants during the 2023-24 offseason that also contained two opt-out clauses, and then worked out a new six-year, $151MM extension last September.
It was surprising to see Chapman and Boras work out such a deal before even testing the market, especially when Chapman was so close to free agency, yet Chapman’s desire to stay in the Bay Area helped pave the way to a new agreement. As much as Boras has the reputation of “pushing” his clients towards the open market, the agent has negotiated plenty of high-profile extensions during his long career, so it shouldn’t at all be taken as a given that Bregman could be playing elsewhere in 2026. Indeed, given how much mutual interest there seems to be between Bregman and the Red Sox, it may be more likely than not that Bregman could indeed find himself as a Fenway Park cornerstone.
He’s opting out
That doesn’t mean he won’t re-sign if the Sox are willing to pay up. And with the financial flexibility they have after dumping Devers, I would say it’s very possible that they are willing to. 5 years, $160 million or so should get it done.
Bregman and his agent are will probably be aiming for 200 or so which the red sox should rightfully balk at.
So add 3 more season at 40 per ? Idk, Boston should pay that imo
sure but he’s going to be looking for 5 years minimum
acell
“he’s going to be looking for 5 years minimum”
He’s probably looking for money, not years. Money is what buys stuff.
There’s almost certainly a 1 or 2 or 3 year deal that he would agree to.
I’d be shocked if he signed for a one year deal or even a two year deal. At that point he might as well just opt into his last 2 years.. Maybe 4 but no less than that.
acell
I’d be shocked, too.
But if he’d almost certainly take 1/$100 if someone offered.
Or 3/$150
Money is what matters. Not years.
Teams, of course, would rather offer 10/$200 than 3/$150.
These statements about minimum years or max years, don’t really make sense.
sure but most players and teams prefer longer term but it means more money. I doubt anyone is going to offer 3 at 150 or one at 100.
acell
“I doubt anyone is going to offer 3 at 150 or one at 100.”
Of course
The point was that a contract can be structured to meet whatever years and whatever money someone wants.
If you want to pay him for just 3 years instead of 5, you’ll have to pay him more than 3 years worth of money in those 3 years.
And if you want to pay him less than, say, $35 million a year, then you need to pay him for more years.
Juan, the focus is on years with this next contract. At this age, a two or three year deal is not going to happen. No way no how.
Your point on the money is a given. That’s what this shorter deal was all about. The player gambles takes a shorter deal, proves he’s worth the money and now the five year deal becomes real.
Both the tigers and the Astros already offered five years before this season. For some crazy reason he wanted to play in Boston so he gambled and had a prove it year.
GRSW
“At this age, a two or three year deal is not going to happen. No way no how.”
You don’t think he’d take 3/$150? How about 3/$180? 3/$200?
As I said, at some point he absolutely would take the shorter deal.
If his offers were 1/$100 and 10)$100, which would be take? The shorter one – of course.
Players don’t care about how many years. They care about how much total money. Why on earth would they care about years?
He took the shorter deal because he thought he’d make more money overall.
It’s about money.
Thank you making a point no one needed you to make. No team is offering Bregman $50 million a year, so obviously both the years and the total value are important. The hypothetical you keep bringing up will never happen.
I mean, what if he were offered a billion dollars to play a month tho.
Agreed that the years and total value are both important. The player wants the most most they can get, but the team cares about the average annual value which figures into their luxury tax calculation.
They care about years due to security and peace of mind. Many athletes at some point suffer a significant injury and all eventually decline. A multi year deal and total $ equally financial security and a safety net.
rare
“The hypothetical”
Since I can’t read Bregman’s mind I have to use hypotheticals. You understand that, right?
Tigers
They care about money. Money is security, not years.
Again, he’d take 1/$100 before he’d take 10/$100. Because that would give him more security/money
Juan, I disagree with you based on reality. No one is going to offer him 3×50 for 150. This is Alex Bregman. .270 hitter, 22 home runs. Gold glove at third.
He will want a five year deal at this age. He can’t keep gambling against health and injury.
He’s watched himself miss a month with the quad strain. As a player reaches 31 or 32 they realize they’re one bad step away from missing a year.
At this point, Alex wants long-term security at the going rate.
Not 3×50, which, of course will not ever be offered to him at this point.
HHe’ll take 6×35 or something like that. 6×32? 5×35 or 37?
1 for $100,000,000 rather than 10 for $100,000,000 ??
That’s not hypotheticals. That’s ridiculous, what are you talking about Kind of stuff.
GRSW
“No one is going to offer him 3×50 for 150. ”
Ugh. The people on this site 🤦♂️
AGAIN. The point is, why would he care about years instead of money? If he could make the same money (present value) in fewer years, he would absolutely take that.
“Alex wants long-term security at the going rate.”
You don’t think he’d take above the going rate? Of course he would. And if it was enough above the going rate, he’d take fewer years.
Tigers
“total $ equally financial security”
Total money (present value) = financial security regardless of years.
GRSW
“HHe’ll take 6×35 or something like that. 6×32? 5×35 or 37?”
Maybe we can work with this
What’s the difference between those deals?
Do you think he’d rather have 6/$32 or 5/$37
Why?
What if it was 5/$40?
Why?
I see what you’re doing Juan. You make sense now.
Not much difference between the five and six year deals. I’m just trying to give a range what I think might happen and what his value may be at the end of the year.
Something around those numbers? I don’t know, just throwing stuff out there.
5 years at 40 million per? Not happening. Five at 37 is a MAJOR reach, but maybe the Tigers do something crazy like that? And if they do, there’s probably going to be deferrals, as teams have entered those as Vogue now..
And thinking about it further that’s really really a stretch. Let’s go back to five at 32 per as maybe what might happen for a guy like him.
But the 100 million for one year is unrealistic. It’s not part of the equation. It’s not part of the peripherals and it’s not part of the proposal outlook in any way whatsoever.
GRSW
“It’s not part of the peripherals and it’s not part of the proposal outlook in any way whatsoever.”
No one said it was.
Again. The point is that if the dollar value were enough (whatever that is, I’m not in Bergman’s mind to know – so I have to use some obvious hypotheticals) he would absolutely take a shorter term deal
He would take 1/$100 over 10/$100. And almost certainly over 10/$150. And probably over 10/$200.
JuanUribeJazzHands
Ugh. The people on this site
==================
I think everyone should focus on ‘overall terms’ instead of hypotheticals that will never happen. Hmmm, $100M for one year or $10M a year for 20 years?
Juan: I don’t think you can argue that it is all about the money. Players take into consideration the city, if the team is competitive, the coaching staff, etc. Of course anyone would take the $100 mil for a year and look at the best option the following year, but as we all agreed no team is going to offer that.
A player may take a longer cheaper deal for a team they really want to finish their career with and request a no trade clause. If Bregman feels strongly about staying with the Sox, he may be open to less money. He may feel that ballpark will give him the best opportunity to pad his numbers for his bid for the Hall of Fame. That may be more important than the money to him. Who knows.
UPDK
“I don’t think you can argue that it is all about the money. Players take into consideration the city, if the team is competitive, the coaching staff, etc.”
Of course
But that’s completely irrelevant if we’re talking about deciding between to offers from the same team since, all those things are the same in either case
Why would he be deciding between two offers from the same team? Your point had been that money was all that matters. A team is going to make one offer and if that doesn’t work they negotiate with the agent. No team is going to say you can either take a 1 year for $100 mil or 10 years for $100 mil. That doesn’t make any sense.
UPDK
“Why would he be deciding between two offers from the same team?”
Going year to year or signing an extension – with the same team. In the same city.
“That doesn’t make any sense.”
Nope. And that’s not at all what I was saying.
You are assuming the team is going to give him two completely different options. You can either sign with us for one year at this salary (which you are indicating would be higher) or can sign with us for 5 years but we will only pay you this much per year (lower than the one year).
The article said he would bank what he made this year and look for a long-term commitment. There was nothing about a 1 year high dollar deal being discussed.
UPDK
“You are assuming the team is going to give him two completely different options”
No. I’m not.
I was exaggerating a difference to make a point and forgot how bad the average person is at non-concrete thinking.
It has nothing to do with us lacking the ability to process what you are saying. You had said it has more to do with money rather than years and that money is his job security. The point that others made is that his preference may be to get a long-term commitment with the team he wants to stay with. My point was that if he were comparing dollar amounts from different teams, he may take less over a longer timeframe to be with the team he wants. In other words it is not all about the money.
UPDK
“My point was that if he were comparing dollar amounts from different teams,”
Sure.
This discussion started out about whether or not his not starting the season in the majors (service time manipulation) could have impacted his extension.
Thus, we were only talking about him signing with one team.
no this conversation started out about Bregman getting an extension and what it would take to sign him at the end of the season.
acell
“no this conversation started out about Bregman getting an extension and what it would take to sign him at the end of the season.”
Oops
Correct. That was Anthony.
The point remains the same, though – comparing contract offers from the same team
Juan- I will simplify my point to be sure it is matching up what you are saying. In my opinion, he is looking for a long term contract so he can be with the team he wants to be with and not take a chance on ending up with another team if he just took a 1 year deal and the team decided to go after someone else the next year. This is why I had said it was more than just the money that will influence his decision.
Someone else had made the point of job security in the form of a long term contract and you made the point that money is job security. In my mind, if he takes a bunch of money for one year and something happens that makes him lose his market value such as an injury he would be screwed. If he signs for 4 or 5 years that won’t be an issue.
UPDK
“In my mind, if he takes a bunch of money for one year and something happens that makes him lose his market value such as an injury he would be screwed. If he signs for 4 or 5 years that won’t be an issue.”
My very first comment on this topic
“He’s probably looking for money, not years. Money is what buys stuff.
There’s almost certainly a 1 or 2 or 3 year deal that he would agree to.”
Say, for example, he thinks he can make $200 million over the rest of his career.
He can sign a contract now for X years and $200 million
Or, he can sign a shorter term deal for a high AAV that reflects the risk that you’re talking about.
He doesn’t care about years. He cares about money.
Of course, he’d rather have one big guarantee, but there there’s a short-term deal for some amount that he’d think would get him more overall.
So, 6/$200 or 1/$100 (which isn’t going to happen, of course. I just use that to make the obvious point) he’d take the 1/$100 because getting 5/$100 (less than that because of net present value) is a relatively safe bet.
The reality tho is he’d likely b offered $38-40M AAV on a one year opposed to $200M/6 years, if $200M/6yrs were his market.
I understand what you are saying, but if he is looking for the highest short term deal he can find, he will likely need to move to another city.
The Sox would be looking to lock him up for the long term, there would be no reason for them to sign him to an inflated one year deal. He is making an average of $40 million with his current contract (granted a portion is deferred), and I don’t see the Sox turning around and offering him a one or two year deal worth much more than that.
I still believe his priority is a long term deal rather than more money for a year or two. We will see who is correct when he gets his next contract.
UPDK
“I still believe his priority is a long term deal rather than more money for a year or two”
His priority is more money overall.
There are two ways to get there
1) a long term deal
2) multiple short-term deals
1) provides more security. The money is guaranteed
2) has more risk. But at some point the potential reward becomes worth it – is the point I’ve been trying to make.
Not if past precedent holds. He turned down Houston’s offer last winter because it wasn’t for more per year than the amount he made his final season in Houston in 2024. So that means this winter he’ll only consider offers that have an AAV of $40M+. Bregman has always been all about the money.
Mets need to trade Baty/Vientos/Mauricio/ for whatever they bring back and add a consistent bat.
200 million no thanks. Bregman doesn’t seem to be a 35 million dollar a year player. 35 million for one year risk ok I’ll buy, for 4,5,6 years no thanks.
Well you won’t get him! Oh no I won’t have to pay a premium for the players decline oh no.
Thats – Agreed! Even the NESN hosts acknowledged yesterday his season is an outlier and he won’t even finish at .300 BA. He’s a good player but he’ll likely never have this good a season again.
It’s funny there’s all kinds of people on here who always refer to the 80s, 90s and yet they don’t remember free agent guys in their 30s would sign for one or two year tops in their 30s because teams knew decline was incoming but everyone wants their team not to be cheap and buy a free agent for 6,7 years at age 31 lol.
That – I think it’s a reflection of today’s society, people love to take risks and gamble. They don’t care if it doesn’t work out, they don’t understand the concept of throwing away tens of millions of dollars.
They even say “give the player whatever he wants” …… it leaves me speechless.
I think he will age well in Boston. Perfect ballpark for him and he’s proving that this season
He also got hurt again which is a concern especial with him aging.
Big – Except his splits totally disprove that.
Home .279 BA and .867 OPS
Road .317 BA and .955 OPS
@Fever- that’s actually a good sign he can remain great in Boston and that 2025 is not a total outlier, because historically before this season he was the greatest non-Red Sox Fenway hitter in stadium history.
High – Harmon Killebrew has a career 1.038 OPS in 582 PA’s at Fenway.
Bregman has a career 1.006 OPS in 258 PA’s at Fenway.
Going into his age 32 season coming off what is essentially a career year, I think the best Bregman should be able to get is like 4 years/$150M to 5 years/$175M to make the whole Red Sox deal equivalent to 5 years/$185M or 6 years/$210M but I don’t think he should get more than 4 or 5 additional years and really should probably be kept to like 2-3 years aka if I was the team and I could do so, I’d trigger an opt-in for the next two years/$70M, hope it works out and walk away no matter how those two years play out.
Nolan Arenado should stand as a cautionary tale for any team considering giving him long term money. There are similarities between the two players beyond just playing third base. Boston should walk away if he opts out. They can cover 3rd with their young players. Veteran leadership can be had at way less than $35 million per.
Gotta pay somebody and he will be cheaper than bichette
They don’t need Bregman or Bichette. They need more starting pitching. That’s where their money should go.
Who’s going to drive in all their runs the Don ? Some unproven 22 year old ?? Sounds like a recipe for 3rd place in the AL east just to save a few bucks 🤔 come to think of it – that’s exactly what the Sox will do lol
@Whiffa
Unproven players have been the driving force behind the first place Blue Jays. The Red Sox should have Casas coming back. They could also add a corner bat to platoon with Mayer at 3rd. Maybe they eat the money and move on from Yoshida and that opens some at bats at DH. The bottom line is I believe the Red Sox can compete next year and be better off long term by letting Bregman walk.
First place jays – they been trying to compete for a decade now and it finally come together for them. Compare that to Yankees who compete every year bc they pay free agents what it costs to obtain their services in NY. They always have a couple bad contracts on the books and it doesn’t matter bc it keeps them competitive. Boston needs to be more like Yankees business model and not the blue jays
We’ll have to agree to disagree. I think the Sox should do everything possible to avoid the Yankees business model. They have a chance to get free of bad contracts and rely on young players signed to team friendly long term deals. The Red Sox should stick with the plan and avoid becoming the Yankees. But that’s just me.
Yeah but all post arb contracts are “bad” contracts. They are going to either be overpaying in the short term or in extra contract years or never sign any free agent of note and roll the dice on finding players in career years like small market teams are forced too. They were ready to do it with Soto and they weren’t wrong to do so. Also that Devers contract was great for them (large market teams) even though it was the highest DH contract in MLB history. They just couldn’t get him to DH lol
Gotta pay somebody 🤷♂️. Bregman looks like he will age slowly at Fenway. Lock him up for 5 more seasons, remove the opt outs and let him be the veteran leader on that squad. He is a ws champ ya kno 😉
Big – Marwin Gonzalez is a WS Champ too, should we bring him back to Boston as well?
For your soft ball league ? Go get him ! Might give your squad some diversity
Big – Nahh, my softball league already has cheaters in it so don’t need more for diversity ;O)
🤣
Don – The Red Sox could never use the Yankees BM because the Red Sox are focused only on the biggest profit possible. I don’t ever see them going back to a Top 3 or even Top 5 payroll team under the current ownership, or breaking even in their bottom line like the Yankees have done.
That is one reason why the Sox are focused on signing rookies so quickly. Someone like Rafaela could be a .585 OPS guy for the next 6 years, but management won’t care because he’s versatile and cheap.
That’s one thing I strongly disagree with the Yankees on, their no-extension policy. They need to find some middle ground.
Good post, Don. I think the Red Sox will stick to the plan. Regarding Bregman, I think the Red Sox may pay a little more or add a year more than they should because they value his veteran leadership.
Don- Jumping into this conversation late. I agree that the Sox should not be following the Yankee model of overpaying for aging veterans. On the other hand, there is no guarantee that Casas is going to come back and stay healthy/put up decent offensive numbers; or that all of our youngsters are going to be a success.
Yes you absolutely can have great years with a bunch of unproven players, but since they are unproven you are just as likely to have them be a complete bust. I think Bregman has proven himself beyond just his bat (which of course is going to deteriorate in time as does every player). You need to have those veteran leaders who stay with a team and act as an additional coach on the field and motivator for the young/developing players.
`That doesn’t mean that you have to fill the roster with overpriced players well past their glory years, but investing in a few veterans can be good business. In my opinion, Bregman is someone who is worth the investment. I don’t see him as someone whose offense is going to fade quickly. That doesn’t mean he is going to be someone you expect to carry the team toward the end of his contract, although I expect him to age better than Devers. We will see how he finishes the year, but at this point I would be disappointed if he is not signed to an extension.
why would the sox sign Bichette? regardless paying somebody for the hell of it is a way to get your team into trouble
Boston lacks no funds. They can blow right past the salary cap every season and never miss a beat. So why not sign both for the hell of it lol
I mentioned Bichette only bc he’s going to get more total money than Bregman
Don – Great post! Yeah this is Bregman’s best year by far since 2019, and it’s not even a year …. it’s just 73 games and his numbers have declined 3 consecutive months.
Any team dumb enough to give a massive contract in this situation deserves the pain it will likely bring.
As much as I am a fan of Bregman, I think I’d have a really hard time going out 6 years from now. I do believe his style of hitting plays extremely well in Fenway, and it is sustainable for at least 3-4 more years before a sign decline. The Monster is his best friend history shows hitters that learn how to use it to their advantage can play into their mid-late 30’s and still have a lot of success.
It’s just that age where the defense starts to give a little and the offense starts to stutter for more 3B.
I’d much rather they go after Skeenes to partner with Crochet for the next 5 years, as the offense will still be strong without Bregman in the lineup. I still Pete Alonso would rake at Fenway and would be money better spent at 1B than Bregman at 3B. We have plenty of guys that could take 3B over, and Alonso may hit 60 bombs in a Red Sox uniform.
I think we’d all prefer Skenes but I doubt he’s getting traded anytime soon.
Its Boston. They can and should do both. Now will they? That’s a different conversation.
I don’t see a need to extend Bregman. If some other team wants to give him say 5/160 or whatever, go for it.
He’s a good player, but let Arenado be a warning for 3B who were amazing and then fell right off a cliff in terms of production. 7.9 bWAR at 31 to 2.2, 2.5 and now 1.1. he has played the majority of games in those seasons as well. The bat went from an amazing 151 OPS+ to 108, 102 and now 86.
I am ok with paying a premium for a guy if you get a chunk of their prime. But the length here scares me with his age and that hamstring injury that seemed to pop up out of nowhere.
They can play Mayer at 3B, provided he’s health and Story doesn’t opt out (which is sitting at a 99.9% chance he doesn’t opt out but a bit can dream).
The FA class overall seems weak which is unfortunate.
My nerd Tigers will once again sit alone in the stands and watch as the quarterback walks away with the cheerleader as she turns and sees you and gives you a wink.
Well, they still have Blaze….wait….what?…aww, never mind.
you mean the guy currently batting 0.83 with his new team? small sample size for sure but not a fast start.
let – The bell Tolled yesterday, 6 runs (5 earned) on 2 homeruns …. not the best of starts for his first AAA game. I really don’t see him getting called up this season.
FPG
1st inning
4 hits,2 home runs – 1 a grandslam,6 runs -5 earned
2,3,4,5th innings 42 pitches
4 shutout innings
Maybe nervous being with a new team. Don’t give up on this guy yet.
cdc – I would never give up on anyone after just one bad game! LOL!
First inning blips- after all the runs in the first he went 5 with no runs
I seriously don’t understand how Breslow operates- let Heineman walk, trade away a good 1B prospect, trades good prospects for a worse version of Fitts—geesh
let Heineman walk
=======================
And after such a long and successful career with the RS. The HBP he got on 4/21/24 is a day that will live in the hearts and minds of Red Sox Fans Everywhere.
Tar – The Priester trade is probably second-worst to the Sale trade, but there could be more as traded prospects develop.
This explains how Breslow operates:
sports.yahoo.com/mlb/article/inside-the-absolute-s…
Signs of a front office losing cohesion
The tension inside Fenway Park isn’t new. It has just evolved.
Manager Alex Cora and chief baseball officer Craig Breslow have not seen eye-to-eye on the direction of the team. Cora wants to win now. Breslow, like Chaim Bloom before him, was hired to build a sustainable future. The last time Cora found himself misaligned with the head of baseball ops, Bloom was fired. Breslow arrived shortly after and re-signed Cora to a three-year contract through the 2027 season that pays him $7 million annually. After the Red Sox finished 81-81 and out of the playoffs in 2024, Breslow’s first season at the helm, the team went out and acquired ace pitcher Garrett Crochet and Bregman, signaling a shift back toward contention. Owner John Henry celebrated with a cigar.
Even then, Cora wasn’t fully on board with how the front office wanted to manage the roster and player development. This season, Cora has managed like someone who knows his legacy is on the line, leaning into experience over upside, even when it conflicts with the long-term plan. He benched top prospects and left-handed sluggers Marcelo Mayer and Roman Anthony against left-handed pitching, despite their strong minor league splits, opting for veteran right-handed bats in Rob Refsnyder and Romy Gonzalez. The choice underscored the ongoing friction: Cora’s focus on winning now clashing with a front office preaching sustainable growth.
“This team is supposed to play better baseball and be in the hunt. We’re not there yet,” Cora said last week. “My job is to try to maximize matchups and help win games. We haven’t done that.”
Meanwhile, Breslow has grown increasingly insulated. Multiple sources within the organization describe a front office losing cohesion. Staffers who helped build four championship teams — veterans of the Theo Epstein, Ben Cherington, Dave Dombrowski and Bloom regimes — now feel shut out of the operation. The collaborative spirit that once defined Red Sox baseball operations has frayed.
The discontent intensified in May 2024, when Breslow brought in sports consulting firm Sportsology to conduct an organizational audit. The stated purpose was to streamline baseball operations. In practice, it triggered a wave of firings and accelerated the marginalization of some of the longest-tenured voices in the building, characterizing the cultural shift to align more with Wall Street efficiency.
One of the clearest signals came during an internal team Zoom meeting earlier this season. Toward the end, Carl Moesche — the Red Sox’s scouting supervisor and a team employee since 2017 — thought the call had ended. It hadn’t. As the meeting wrapped, his voice cut through a quiet moment.
“Thanks, Bres, you f***ing stiff,” Moesche said, according to two team sources.
The words landed like a grenade, and Breslow fired Moesche.
Moesche did not respond to a request for comment.
The blockbuster trade of Rafael Devers was a culmination of eroded trust, fraying relationships and a deeper breakdown inside one of baseball’s most visible franchises.
The blockbuster trade of Rafael Devers was the culmination of eroded trust, fraying relationships and a deeper breakdown inside one of baseball’s most visible franchises. (Grant Thomas/Yahoo Sports)
(Grant Thomas/Yahoo Sports)
Dysfunction on the field and hands-off ownership
The internal strain has bled into how the Red Sox handle their players, too.
The coaching staff has grown frustrated with the state of player development, specifically how much emphasis is placed on swing mechanics and hitting data, often at the expense of fundamentals. That imbalance, coaches believe, traces back to the Bloom era and has only accelerated under Breslow. One example cited is rookie Kristian Campbell, who has made a string of routine errors at second base since being called up. He’s not alone; as a team, the Red Sox lead all of baseball with 64 errors, one more than the Colorado Rockies and 17 more than the third-place Los Angeles Angels.
Another error came during Roman Anthony’s debut, when he misplayed a ball in right field. The next day, Anthony was sent out to run outfield drills in front of the media. Multiple people in the organization noted that under previous regimes, that kind of instruction would’ve taken place behind closed doors. This time, it felt like a message from the coaching staff to the front office. One team source described the message as deliberate: “This is what we still have to teach, at the big-league level.”
Ownership, meanwhile, has grown increasingly hands-off. Since Epstein’s tenure, Red Sox owners have often acted as active stewards of baseball operations — meddling at times but always deeply invested. But now, multiple sources say there’s a growing sense that John Henry delegates the day-to-day operations of the Red Sox to team president Sam Kennedy. That detachment has created an opening for divergent priorities across Fenway Sports Group’s portfolio. Case in point: Just days before the Devers trade, FSG made headlines in England by spending a record £116 million ($157.7 million) on German star Florian Wirtz at Liverpool. Meanwhile, in Boston, they were preparing to offload their franchise star.
The optics are staggering. On a picturesque Sunday afternoon, the Red Sox swept the Yankees. Hours later, they traded Devers. No farewell. Just silence. One staffer described the situation as “an absolute s*** show.”
Kennedy, Breslow and Cora did not respond to requests for comment.
For a franchise that once set the standard for modern baseball operations, dysfunction has become the new normal.
Bregman is exactly the type of player you want leading by example for a young team. He also hits and plays defense at an elite level and should continue to do so for a few more years. With the money they are saving by trading Devers they should basically let him determine his price, and pay it. I am extremely excited by the young core they are developing,but they NEED Bregman types in that locker room to steward the kids.
Cheap – Blank checks are never a good idea, especially with the greedy Bregman and Boras. The Devers money would be better spent on much-needed starting pitching, relievers, catcher, and possibly first baseman.
Sox have Story, Duran, Crochet etc as leaders in the clubhouse.
Cheap, then hire Tony Robbins. He’ll be a lot cheaper than paying Alex Bregman the next six years.
Gary – This is another example of the Red Sox being inconsistent at best or dishonest as usual.
They have been harping over and over how they will give longterm contracts only to players in their 20’s. Rizzo the team’s mouthpiece was spreading the exact same crap just yesterday, “we want them in their 20’s” ….. if they then go ahead and give a monster contract to a 32-year-old they will once again be exposed as an organization that can’t be trusted.
FPG
I’m thinking tonight is just about a must win.. do not want a 3 game losing streak with May going tomorrow. Did you see my post about signing Bregman???. I know you would rather allocate money elsewhere,but we do need veteran , productive leadership. Do you agree with that???
I assume 5 at around “$170 . Takes him to his age 37 season ,, should be productive offensively and defensively for at least a few seasons. Injuries can and will occur,but I would bet on this type of player …
cdc – We both would like Bregman signed, but we differ on how much to give him.
Looking at the Houston series, Sox should easily win it.
Tonight – Crochet vs a guy who hasn’t pitched since May 2024
Tomorrow – May vs a guy with a 7.43 ERA
Did you see Cora didn’t even know who they are playing this weekend!
Sandy on Friday, should be an easy Sox win. Same on Saturday against Quantrill, easy Sox win.
too high an injury risk. He is a good player and everybody hits better in Boston.
A contract for 5 years at approximately $170 million should get it done. Takes him to his age 37 season. I would think he will be highly productive for at least 3 or 4 of those years. A gold glove caliber 3rdbaseman, an above average hitter with some power,a leader and already a champion. If you are going to pay someone , he checks all the boxes.
cdc – And yet he didn’t sign until the day before ST because only two other teams (Astros and Tigers) made him an offer. So why wasn’t he appealing to any other team?
FPG
Maybe that late , some teams,most teams ,have there budgets already set .. I don’t know exactly . But the addition of a player with Bregmans abilities would only enhance most teams.. there are only so many teams that can afford a player of his stature. Bottom line is the Sox will be a better team with his services for the next several years. Of course they still will need top shelf starting pitching.
cdc – Teams didn’t value Bregman very much, which is why he went all offseason without getting an offer that was acceptable to him.
To Breslow’s credit, he didn’t want Bregman but agreed to sign him ONLY if his price dropped considerably and length dropped to 3 years.
As for better team with him, you do realize Bregman at 3B means either Abreu or Duran gets traded. I don’t see how that makes them a better team. LOL
Fever, don’t discount the weight of the qualifying offer either. Bregman was saddled with that last time around
GaSox – Yeah I had that in mind, but typically it doesn’t impact the top tier of free agents …. it’s more the lesser free agents.
Did you see Bregman’s beer commercial? His name is on the beer, sounds like a negotiating tactic. LOL
It tends to hit Boras clients harder than most others. I think he starts off so high on asking prices, that added weight depresses the market. By the time he comes back to earth, teams either allocated payroll already, or, have made some QO signings and are concerned with losing too much of their draft and bonus pool.
You lose too many top round picks, that 10% every team builds in to go over without penalty shrinks pretty quickly – especially for tax payors.
I know Bregman’s wrc is 147 now and should he keep that production up its easy to see him getting the contract he wants..but what if he doesn’t? Bremen had a monster March/April. He’s been good after that but his production is continuing to drop. What if he hits a slump? What if he gets injured again?
He very well could opt out but this may not be the platform year he wants. If he can produce from this point on the way he did in April, THAT might write a $200 million dollar contract in stone but I think the potential slump or injury is to significant to set any expectations.
Also, I find it difficult to believe his early production is true form Bregmen. Any batter can have an elite month.
Scm
I think his career will tell us he is that player.. injury concern can and will happen. Bregman is a player that has proven his worth. This and every team needs veteran leadership,and he brings that quality as well as offensive and defensive production. The young players gravitate towards him . IMO he is a must sign.
cdc – Think about it …. you are saying we should ignore the 594 games from 2020-2024 during which he has a .795 OPS and instead give him a contract based on just 73 games this season?
Win with motivated guy for the 1 season (missing time) and let him walk…..easy. He and Boras are cutthroat unsympathetic figures. It’s a 2-way street with owners and UFA’s using each other.
I’d be willing to listen, but I otherwise agree with you. Age 32 is too old for a l/t contract. History says he’ll have 1-2 good years before he starts declining
JB
It’s absolutely fine to sign declining players.
That just needs to be factored into the contract terms and the team that you’re building around them.
I’m sorry but he’s not worth 40m$ a year
Love everything about this guy but @ this stage of his career 40m a yr is too much. Sox should let him walk.
If Bregman’s smart he’ll delay free agency for one more year and take another inflated salary. The bottom line is he hasn’t been worth even 5 wins since 2019 and teams will price that track record accordingly.
IMO the smarter play is to lock up as much guaranteed $ after this season. He’s getting older. One bad year or injury would lose him more money than another good year would gain him
That being said, he has made a ton of money in his career already so it doesn’t really matter and he should do whatever is going to make him happiest over the next 5 years
Who really cares? What about the female umpire? That’s clearly the most important thing going on in baseball….🤦🙄
Worth every single penny.
He’s not worth it. Good player, 4 years at $120 would be the most I’d offer him. Otherwise let him walk and someone else can overpay for a guy who is player for that one big contract before he calls it in.
padam
“Good player, 4 years at $120 would be the most I’d offer him”
You’d let him sign elsewhere for 5/$121? Just one million bucks in 2030 plus a lower AAV over the next 4 years. Seems foolish not to accept that if you’d accept 4/$120.
How about 5/$125 or 5/$130? There’s, if you’re being honest, and not an imbicile, a 5 year deal that you’d agree to.
These “I’d only give him…” comments really miss the reality of the situation