Early Trade deadline deals the selling Sox should make

[Behindenemylines]

Sox still need what they needed over the winter: minimum two right-handed power bats. They have less than a hand full of three run homers this season. Hard to score a lot of runs without hitting homeruns.

[Sthpaw777]

20 hours ago, Nick said:

We got Abreu for Vazquez rental. What can we get for Chapman?

He’s got another year option and if he goes to a good team I’m sure there’s a good chance he'd want to opt in…so he’s not just a rental. 
I think Breslow should ask for a top prospect with a big bat to headline any deal.

[notin]

53 minutes ago, Sthpaw777 said:

He’s got another year option and if he goes to a good team I’m sure there’s a good chance he'd want to opt in…so he’s not just a rental. 
I think Breslow should ask for a top prospect with a big bat to headline any deal.

Chapman does have a mutual option, but any team acquiring him will view him as a rental.  As for where he goes, who knows what makes him to decide to trigger his part of the option?  Most likely he only triggers it if he has a bad year, in which case thr team declines it anyway.  Both sides exercising a mutual option is so rare.

As the deal is for two months of Chapman, a top prospect and a big bat is not happening. Not without a third team. No team in the hunt is breaking up their lineup.  It’s surprising that most closers traded at the deadline have more than 2 months left.  Jhoan Duran, for example, had 2.3 years left last year, and he got a fringey top prospect (Mick Abel) plus a 19yo A ball catcher with some promise.  
 

Now two months Chapman himself was traded in 2023 for Cole Ragans plus.  Three years later, he likely won’t command the same price.  If the Sox get one good (not great) player out of this deal, it’s probably the ceiling.  But he’s not some Golden Ticket to patch multiple holes for 2027…

[UtahSox]

I’m getting tired of the Red Sox extending players who are still in the early stages of arbitration and, in the process, inflating their AAV before they’ve truly established themselves. I get it. It’s becoming a league wide fad. But it’s one I wish the Red Sox never participated in. The track record on these deals for RS has been pretty poor. They often turn players who should be movable assets into contracts that are difficult to trade if things don’t go as planned.

They tried to do it with Tristan Casas, and thankfully he didn’t accept. Could you imagine that deal? 

They did it with Brayan Bello, and that contract looks worse by the day. If Bello were still on a standard arbitration path with multiple years of team control remaining, another organization might convince itself it could unlock another level from him, similar to how the Brewers viewed Kyle Harrison. Instead, his contract reduces his trade value and makes a fresh start impossible to facilitate.

Then there’s Kristian Campbell. I never understood the urgency of that extension. Now the Red Sox are committed to significant guaranteed money for a player who may or may not develop into what they hope. At this point, he would likely be viewed more as a throw-in piece than a centerpiece in a major trade.

Even with Roman Anthony after essentially two months of high-level hitting. Don’t get me wrong—I love Anthony’s talent, approach, and long-term ceiling. But we’ve seen him literally get injured twice now from swinging a baseball bat. He played 70/97 eligible games last year, and now has played in 30/61 this year. Injury concerns + just from a roster-building perspective, there is tremendous value in having an elite player under the six years of arbitration control, rather than immediately committing to a deal carrying a $16+ million AAV.  

Rafaela would be making 800k this year vs 6.25m AAV that could have been the difference allowing us to sign Bregman back. 

[notin]

9 minutes ago, UtahSox said:

I’m getting tired of the Red Sox extending players who are still in the early stages of arbitration and, in the process, inflating their AAV before they’ve truly established themselves. I get it. It’s becoming a league wide fad. But it’s one I wish the Red Sox never participated in. The track record on these deals for RS has been pretty poor. They often turn players who should be movable assets into contracts that are difficult to trade if things don’t go as planned.

They tried to do it with Tristan Casas, and thankfully he didn’t accept. Could you imagine that deal? 

They did it with Brayan Bello, and that contract looks worse by the day. If Bello were still on a standard arbitration path with multiple years of team control remaining, another organization might convince itself it could unlock another level from him, similar to how the Brewers viewed Kyle Harrison. Instead, his contract reduces his trade value and makes a fresh start impossible to facilitate.

Then there’s Kristian Campbell. I never understood the urgency of that extension. Now the Red Sox are committed to significant guaranteed money for a player who may or may not develop into what they hope. At this point, he would likely be viewed more as a throw-in piece than a centerpiece in a major trade.

Even with Roman Anthony after essentially two months of high-level hitting. Don’t get me wrong—I love Anthony’s talent, approach, and long-term ceiling. But we’ve seen him literally get injured twice now from swinging a baseball bat. He played 70/97 eligible games last year, and now has played in 30/61 this year. Injury concerns + just from a roster-building perspective, there is tremendous value in having an elite player under the six years of arbitration control, rather than immediately committing to a deal carrying a $16+ million AAV.  

Rafaela would be making 800k this year vs 6.25m AAV that could have been the difference allowing us to sign Bregman back. 

And the risk of watching Anthony reach free agency at 27 was worth all these deals combined.  

It’s not a “league wide fad;” it’s the new economic reality.  And yes, occasionally it doesn’t work out.  Can’t the same be saud for free agents?

The complaints around this “fad” all revolve around who else the Sox could have signed instead. But those players are ALWAYS on the wrong side of 30 and watching their skills fade at various rates. And Ive never once heard anyone say “thank God we signed David Price instead of extending Mookie Betts.”  If you’re going to play in that arena, there are two sides. Also Bregman has a 103 OPS+ this year.  He’s basically another Yoshida - the guy everyone wants to dump.  Is that really the missing piece?  The big difference is Yoshida has only one more year; Bregman cost twice as much per year snd is signed for 4 more years.  Did the Sox really miss out here? 
 

None of these Sox deals really add up to much.  Campbell’s AAV is high end utility infielder money.  As a former Minor League Player of the Year and MLB Rookie of the Month, I think he can at least be a utility infielder.  Bello was good last year (9th in the AL in ERA), but struggled down the stretch and early tjis year.  He was never a top prospect, but he really was establishing himself after a good 2023.  When is a player “established”?  If you wait too long, many players (re: agents) know they can make more money and fewer years in arbitration.  
 

Think of it this way - Anthony’s injury history is not that significant.  While it happened twice in MLB (hardly trailblazing), he really never got hurt on the minors playing the same game.  If he reaches free agency at 27, he could easily make command money than all of these extensions combined.  Think Boston pays it then?

Fans want the team to spend more, but then don’t like it when they do…

[JAG]

on June 5th I really hope the sox aren't in selling mode yet. I still hold out hope that Crochet and Roman come back strong and there is some exciting baseball to watch this year. 

Is there bat available? I highly doubt the Astros will trade Yordan but how about Lowe from the Pirates if they become irrelevant, they may not though they have nice starting pitching keeping them in it

[Sthpaw777]

8 minutes ago, JAG said:

on June 5th I really hope the sox aren't in selling mode yet. I still hold out hope that Crochet and Roman come back strong and there is some exciting baseball to watch this year. 

Is there bat available? I highly doubt the Astros will trade Yordan but how about Lowe from the Pirates if they become irrelevant, they may not though they have nice starting pitching keeping them in it

Crochet has a let issue and my guess is around or after the ASG. Roman hasn’t taken a swing yet. My guys is July for him too..or later. I hope I’m wrong.

[notin]

46 minutes ago, JAG said:

on June 5th I really hope the sox aren't in selling mode yet. I still hold out hope that Crochet and Roman come back strong and there is some exciting baseball to watch this year. 

Is there bat available? I highly doubt the Astros will trade Yordan but how about Lowe from the Pirates if they become irrelevant, they may not though they have nice starting pitching keeping them in it

There will be bats available. 
 

To me, the best fit is Gleyber Torres.  Especially if Anthony is back by July.  Yordan is signed for two more years; he’s not moving…

[mvp 78]

1 hour ago, notin said:

And the risk of watching Anthony reach free agency at 27 was worth all these deals combined.  

It’s not a “league wide fad;” it’s the new economic reality.  

John Henry doesn't want to pay guys market rate. 

Best Red Sox player of this generation gone. Can't pay him! Might as well dismantle and blow up the whole team for 5 seasons.

FA additions: Masa was an import that nobody else wanted (probably still overpaid). Story was damaged goods and probably cheaper than expected (probably still overpaid). Bregman was brought in on a high AAV opt out deal (and it really f'd up the org to do so). 

They extended Raffy after external pressure. The second they got uncomfy, they jumped ship on the only long term big contract they had. 

In order to add a big bat this season, they traded for Contreras rather than go to FA. They couldn't pull the trigger on bringing Bregman back. 

They add extensions for younger players as it adds cost controlled certainty for a few years. Private Equity is able to determine roughly how much they'll be able to extract each season. Set that budget. Tighten those belts! Whether it works or not doesn't matter because the seats are going to be filled and Sweet Caroline will be played. 

That's the new economic reality. Henry is 3rd in MLB revenue, but doesn't want to spend like the Yankees or Dodgers. Henry makes more and more money every year and spends a smaller % on payroll than they did when they won WS every few years. 

[mvp 78]

1 hour ago, Sthpaw777 said:

Crochet has a let issue and my guess is around or after the ASG. Roman hasn’t taken a swing yet. My guys is July for him too..or later. I hope I’m wrong.

Roman has taken "dry swings." If you like that terminology. 

[mvp 78]

1 hour ago, JAG said:

on June 5th I really hope the sox aren't in selling mode yet. I still hold out hope that Crochet and Roman come back strong and there is some exciting baseball to watch this year. 

Is there bat available? I highly doubt the Astros will trade Yordan but how about Lowe from the Pirates if they become irrelevant, they may not though they have nice starting pitching keeping them in it

I'd like Lowe more if he was a RHB. 

[vegasbob]

31 minutes ago, mvp 78 said:

Roman has taken "dry swings." If you like that terminology. 

Kind of like they do in the On Deck area .   I think Anthony will be on deck right about the time July ends, without hyperbole

[SPLENDIDSPLINTER]

The Sox put a lot of weight on both Mayer and Anthony coming into this season. It appears one can't carry this weight and the other is too fragile to carry any weight.

[SPLENDIDSPLINTER]

On the positive side, the Sox did get 2 contributing prospects from the farm, although they weren't the 2 we expected.

[harmony]

On 5/24/2026 at 8:53 AM, notin said:

Two BTV-friendly deals that make sense in one way, but also don’t. 
 

Bello (-18 -actually dropped to -22.2 but SF isn’t backing off on that) to SFG for SS Willie Adames (-18.3).  SF is pitching poor and has a crowded INF.  They’re in last place, and Adames sees his salary jump from $13mill this year to $31mill per for the next 5.   Adames could bring so RHH pop to an anemic Sox lineup, especially if he is already past his historically slow starts at the plate.

The downside - Adames is not a good SS, with less range than Sylvester Stallone.  He does have a strong arm, so 3b is a possibility.  His contract could be dangerous and most definitely will not age well, putting him in the exact opposite position of Bello.  If the Sox do move on Adames, do so with a different bad contract

Trade 2.  Same teams.  Kyson Witherspoon (-16.7) straight up for INF Casey Schmitt (-16.3) .  Schmitt is a RHH StatCast hero at the plate slugging over .500 and being used mostly at DH, but capable of any infield role (although I recommend limiting his time at SS).  Former first round pick could be expendable in SF with the emergence of Bryce Eldridge threatening his time at DH.

Downside - mostly for SF.  While they are having a bad season, dealing for prospects in May/June is some seriously negative PR, and not a message to fans teams with large payrolls like to send.  They might still have tickets available.

It does mean giving up on a first round pick quickly for Boston, but Schmitt was also a first round pick.  

 

A San Francisco blogger lists Casey Schmitt as the Giants' top trade chip:

https://www.mccoveychronicles.com/san-francisco-giants-analysis/107269/the-san-francisco-giants-top-10-trade-chips-2026-mlb-trade-deadline

[SPLENDIDSPLINTER]

20 minutes ago, harmony said:

A San Francisco blogger lists Casey Schmitt as the Giants' top trade chip:

https://www.mccoveychronicles.com/san-francisco-giants-analysis/107269/the-san-francisco-giants-top-10-trade-chips-2026-mlb-trade-deadline

I thought it might be Devers.

[Duran Is The Man]

1 minute ago, SPLENDIDSPLINTER said:

I thought it might be Devers.

he said "top", not "biggest".

[SPLENDIDSPLINTER]

6 minutes ago, Duran Is The Man said:

he said "top", not "biggest".

If the Giants want to trade Devers, they'll have to eat some of his contract, which is something the Sox FO is used to.

[SPLENDIDSPLINTER]

If I was the GM of a MLB team and I had the choice of Contrares or Bregman, I'd take the former. Still confused why a few teams thought he was worth the money he was asking for. 

 

[SPLENDIDSPLINTER]

A 4 pitch inning. I believe that's the fewest pitch count inning this season.

[SPLENDIDSPLINTER]

...

[vegasbob]

8 minutes ago, SPLENDIDSPLINTER said:

If I was the GM of a MLB team and I had the choice of Contrares or Bregman, I'd take the former. Still confused why a few teams thought he was worth the money he was asking for. 

 

No question that Bregman on a 4 or 5 year deal was a bad idea. Cubs will eat it . 

[SPLENDIDSPLINTER]

...

[SPLENDIDSPLINTER]

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[Randy Red Sox]

On 5/18/2026 at 7:56 AM, Sthpaw777 said:

Let’s be real…we have some good looking young starters in this organization, but we’re still a mediocre 500ish team. We would have to go over 600 the rest of the way to match last year, which wasn’t even 90 wins. We’re counting on too many 2nd year and 1st year guys. No leadership and a streaky offense. I don’t believe we are good enough this year to be a serious contender against the best teams. I get that the AL isn’t really competitive, but we’re not even serious contenders in a weak AL.

theres a few teams interested in Aroldis Chapman, and with a option for 27 that vests with 40ip we could possibly find that big bat we need.  we don’t have much pure power guys down there that have stood out besides the 6’6 270 lb young (19) and undeveloped Justin Gonzales.

Duran

Contreras

Gray

Are three more that immediately come to mind that could bring something back if they’re performing.

Chapman is simply a rental and as a result will likely only bring back a decent but not great prospect.

[Randy Red Sox]

1 hour ago, vegasbob said:

No question that Bregman on a 4 or 5 year deal was a bad idea. Cubs will eat it . 

meanwhile RSN is loving Durbin

[harmony]

Per MLB Trade Rumors, the Red Sox are exploring the trade market for a right-handed bat while the Arizona Diamondbacks are exploring the market for a left-handed bat:

https://www.mlbtraderumors.com/2026/06/red-sox-trade-rumors-right-handed-bat-eat-money-salary.html

https://www.mlbtraderumors.com/2026/06/diamondbacks-trade-rumors-left-handed-bat-first-base-dh.html

Would either side be interested in a trade of lefthand-hitting Masataka Yoshida for righthand-hitting Lourdes Gurriel Jr., two 32-year-old hitters with MLB career wRC+ of 108 each?

According to Spotrac, Yoshida has guaranteed salaries of $18.6 million for 2026 and 2027 while Gurriel had a 2026 salary of $14 million and a 2027 club option for $14 million.

This season Yoshida has posted a negative 0.1 fWAR and a wRC+ of 96 in 43 games while Gurriel, who is currently on the injured list, has slumped to a negative 0.4 fWAR and a wRC+of 65 in 25 games.

Before the season FanGraphs projected Yoshida with 0.4 fWAR and a wRC+ of 111 in 40 games while projecting Gurriel with 1.1 fWAR and a wRC+ of 106 in 110 games.

The ZiPS three-year 2026-28 projections had Yoshida with 1.1  fWAR in 282 games and Gurriel with 2.3 fWAR in 346 games.

https://www.fangraphs.com/players/masataka-yoshida/31837/stats/batting#zips-3-year-projections

https://www.fangraphs.com/players/lourdes-gurriel-jr/19238/stats/batting#zips-3-year-projections

Buying low on Gurriel would save the significant payroll.

Thoughts?