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    The Time Has Come: Why the Red Sox Must Trade from Their Outfield Depth This Offseason

    The Red Sox have plenty of talent roaming the outfield. There is no reason to delay the inevitable any further.

    Alex Mayes
    Image courtesy of © Vincent Carchietta-Imagn Images

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    Still in just the beginning stages of the offseason, the Boston Red Sox still have a giant logjam at the major league level in the outfield. There are four, and up to six, names that are starting-caliber outfielders on the 40-man roster. and they all have a chance to break spring training with the major league club in 2026. As we’ve covered multiple times here at Talk Sox, the free-agent market for virtually every position is incredibly thin and offers very little upside outside of the top four or five names that are available. While Craig Breslow expects the Red Sox to add through free agency, any huge impact will likely have to come through trades. Since the Red Sox have so much talent in the outfield, let’s take a look at the pros and cons of trading any of Jarren Duran, Wilyer Abreu, or Ceddanne Rafaela.

    For the sake of this exercise, we'll consider Roman Anthony safe... unless the Dodgers put Shohei Ohtani on the trade block.

    Jarren Duran

    Seems best to start with the one who currently has rumors attached to him as the GM Meetings in Las Vegas wrap up. Jarren Duran’s name has come up in trade rumors since his break out 2024 season when a portion of the media and fan base believed the team should have sold high. He followed that season up with a solid, but far less impressive, 2025 campaign. The biggest pro of trading Duran is that it opens up left field for Anthony and allows Rafaela and Abreu to play their natural positions in center and right field. Both men just won Gold Gloves and shouldn’t be moved off them for anyone else on the roster.

    Can Duran even play center or right? Technically yes, but he’s best suited for left field, as his throwing arm leaves a lot to be desired from any other outfield position. He continues to be an obvious fit as the centerpiece of a trade package to a team that’s willing to deal a starting pitcher back to the Red Sox. The flip side here is that Duran is a locker room favorite and a team leader. His absence would leave a void that would have to be filled, which isn't as easy as simply buying a veteran in free agency—Duran is one of the longes-tenured members of the roster.

    Wilyer Abreu

    Fresh off his back-to-back Gold Glove wins, it may be hard to envision the Red Sox trading the rising star that is Wilyer Abreu. Stranger things have happened though. Abreu spent a portion of the last half of the season on the injured list and when he returned, he was a shell of himself. That being said, he was second on the team in home runs and served as a spark on both sides of the ball when healthy. Similar to Duran above, the biggest pro in trading Abreu is opening up a full-time position for Roman Anthony. Anthony played a great right field before he was injured, so there should be a decent level of comfortability with him taking the position over full time.

    Abreu, with an extra year of team control and several birthdays separating him from Duran, should fetch a nice haul in a trade. The biggest con in trading him is that the Red Sox may actually be selling low on his potential; he continues to get better with each passing year and hasn't even had a chance to play every day without the benefit of a platoon partner. His absence would leave a lineup that already lacked power with even fewer options. We’ve talked about how thin this free-agent market is, and unless the team plans to bring in both Kyle Schwarber and Pete Alonso in free agency, Abreu’s departure would come close to zapping the team of its power entirely.

    Ceddanne Rafaela

    While it would be shocking to see the team trade Rafaela, it’s not out of the realm of possibility. He’s a first-time Gold Glove winner and plays arguably the best center field defense in the entire league. He’s shown flashes of potential on offense and has a propensity for coming through in big moments. Typically though, his offense is boom or bust and he’s best suited for the bottom of the lineup. His contract makes him a steal for most teams, and that’s likely the biggest reason he could be available for the right price this winter. The only positive that can be found from trading him is that the team could potentially upgrade his position with an offensive-minded center fielder like Cody Bellinger, but that also comes as the biggest con of moving him: the team would lose its best defender. At such a premium position like center field, losing Rafaela’s glove would put the team in a much worse position than they current are.


    Masataka Yoshida was left off of this list because he barely played in the outfield during the 2025 season and honestly, most people expect that he will not be with the club come 2026. He’s never going to live up to his contract, but he has the ability to catch fire in a bottle and be productive. It wouldn’t be shocking to see him involved in a trade with any of the outfielders mentioned above to try and make salaries match for a second playoff-caliber starter.

    The Red Sox have so much talent at positions of need for a lot of teams in the league and they’d be smart to capitalize on that as the offseason begins to progress. Remember, none of this conversation thus far has mentioned Kristian Campbell or Jhostynxon Garcia. With the GM Meetings in the rearview mirror, all eyes turn to the Winter Meetings where Craig Breslow made his biggest trade to date last year. Will history repeat itself this time around?

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    Featured Comments

    9 minutes ago, notin said:

    With Gerrit Cole several years into his $36mill AAV, Skubal is going to break scary records…

    Meant to respond off this but Im jumping tabs too much.  But my point is - with this in mind, arent you GLAD that crochets contract isnt for 3 years?  Because Skubal is gonna change the game, set a new precedent all that stuff and we got our boy locked in first.

    Theres a positive side to going long.  It protects against inflation risk

    Obvs i understand far more dont work out than do but im a cost of doing business kinda guy

    The reason why you cant approach your roster strategy from a standpoint of trying to minimize mistakes and bad contracts and be super shy to take a risk and go long....The reason why you cant go about it this way is simple:

    Scared money dont make money

    You reallllllly dont wanna be scared money at the poker table with sharks like me in the water

    I'm fine avoiding large and long with pitchers. It's not just because of our nice success trading for top pitchers, but also because so many of them fail- often year 1 or 2.

    It makes sense to go large and long on a big bat, this year. We should have a 3-5 year window.

    1 hour ago, drewski6 said:

    The reason why you cant approach your roster strategy from a standpoint of trying to minimize mistakes and bad contracts and be super shy to take a risk and go long....The reason why you cant go about it this way is simple:

    Scared money dont make money

    You reallllllly dont wanna be scared money at the poker table with sharks like me in the water

    And yet the Brewers made the postseason while the Mets got to stay home and watch the Brewers…

    2 hours ago, notin said:

    The thing is, the shorter deals expire faster.  If I sign Michael King to a 3 year deal, and he is out for the first two, that deal is over 3 years from now.  But if you sign Tarik Skubal to a 10 year deal, and he has arm problems early on, youre paying him for 10 years and he might never be the same even when he returns.

    Price signed for 7 years and couldn’t go two years without getting hurt .  And he was also never the same again.   And had that injury happened two years later, it might not have mattered to Boston, because he had an opt out after 3 years he probably (?) would have exercised…

    Yeah look that's silly, you're right here.  But at the end of the day if you don't pay the price of admission you don't get into the show. But go down the list of past world series winners, almost every single one of them has big name free agent pitchers on their roster. 

    You get what you pay for, and yes that involves risk.  But the boy who never asks a girl to dance never dances with a girl. 

    39 minutes ago, Hugh2 said:

    Yeah look that's silly, you're right here.  But at the end of the day if you don't pay the price of admission you don't get into the show. But go down the list of past world series winners, almost every single one of them has big name free agent pitchers on their roster. 

    You get what you pay for, and yes that involves risk.  But the boy who never asks a girl to dance never dances with a girl. 

    Not all the champions have big name free agent pitchers on long, large deals.

    I only had to go back to the 2023 Texas Rangers.  Eovaldi was on a 3 year deal.  Sure they had deGrom, but he only started 6 games that year.  Technically, they did HAVE the big free agent pitcher in deGrom per your point.  But per mine, they proved they could win without him.

    Also the 2021 Braves, 2017 Astros and 2015 Royals did not have any big free agent pitching contracts…

    18 minutes ago, notin said:

    Not all the champions have big name free agent pitchers on long, large deals.

    I only had to go back to the 2023 Texas Rangers.  Eovaldi was on a 3 year deal.  Sure they had deGrom, but he only started 6 games that year.  Technically, they did HAVE the big free agent pitcher in deGrom per your point.  But per mine, they proved they could win without him.

    Also the 2021 Braves, 2017 Astros and 2015 Royals did not have any big free agent pitching contracts…

    So 3 in the past 20 years? and I mean, how many years did those teams suck to get top 3 picks to get there? the braves were horribly for like an entire decade.  We are not a small market team.  It IS possible to win, spend, and develop players.  The Dodgers have a loaded farm system, and spend like crazy and yet still manage to dip below the luxury tax every few years.  The Sox could easily do that with the revenue they have and enjoy sustained success.  They just need the will and the demand for it. 

    1 hour ago, Hugh2 said:

    So 3 in the past 20 years? and I mean, how many years did those teams suck to get top 3 picks to get there? the braves were horribly for like an entire decade.  We are not a small market team.  It IS possible to win, spend, and develop players.  The Dodgers have a loaded farm system, and spend like crazy and yet still manage to dip below the luxury tax every few years.  The Sox could easily do that with the revenue they have and enjoy sustained success.  They just need the will and the demand for it. 

    I named 4 in the past 10 years.  2025-2015 =10.

    Really, it comes down to 4 of the last 11 WSC.  Thats still a significant percentage…

    3 hours ago, notin said:

    Not all the champions have big name free agent pitchers on long, large deals.

    I only had to go back to the 2023 Texas Rangers.  Eovaldi was on a 3 year deal.  Sure they had deGrom, but he only started 6 games that year.  Technically, they did HAVE the big free agent pitcher in deGrom per your point.  But per mine, they proved they could win without him.

    Also the 2021 Braves, 2017 Astros and 2015 Royals did not have any big free agent pitching contracts…

    Somehow the Braves got Morton to keep signing one year deals year after year.

    Please, no Sale.

    You just know what what will happen, if he comes back.

    Can we please... just once...add a pitcher without so many concerns?

    It's like the Sox have hypnotized us into only being able to see hobbled and broken-down pitchers as options.

    1 hour ago, moonslav59 said:

    Please, no Sale.

    You just know what what will happen, if he comes back.

    Can we please... just once...add a pitcher without so many concerns?

    It's like the Sox have hypnotized us into only being able to see hobbled and broken-down pitchers as options.

    What other options are available to us? 
     

    sale’s stuff = Bugatti 

    sale’s body = 1978 ford pinto!!!  But even the pinto occasionally lasted more than 6 months before breaking down!!!! 

    12 hours ago, notin said:

    I named 4 in the past 10 years.  2025-2015 =10.

    Really, it comes down to 4 of the last 11 WSC.  Thats still a significant percentage…

    And of those 4 how many are "sustainable winners"? they were all window teams, with the exception of Houston who did seem to extend their window, but they also started paying guys to do that. 

    You've proven that you don't have to be the biggest spender to win, but I never denied that fact, but it's still ALSO a fact that there is a correlation between spending and winning. 

    The Red Sox have the 3rd highest valuation of any mlb team. Last year they had the 5th highest revenue, but if you exlcude NY and LA the other teams were only $10 million more than them. They've been top 5 the past 10 years, and I'd argue that if you take the losing seasons recently out, given Bostons market size we should be the 3rd highest revenue generating team. 

    There is ZERO reason why we can't spend.  We can spend on players, player development, drafting, coaching, scouting etc etc. The point you're proving is that other things add value and create a winning atmosphere as well but when there is an undeniable link between spending and success a fan of the 3rd richest franchise in MLB should demand his club do both. 

    Henry has spent in the past, he thinks he's the smartest guy in the room and tried to go cheap.  I fully expect he has it in him to pivot back and try to do both.  LA is the model to follow, of course we will never be LA, but we never had to be NY to beat NY but we acted pretty darn close to it to get there. 

    I get there is risk, but to me, there is a difference between not spending heavily on free agent pitchers and then practically never spending.  Crochet was a good move, but aside from trades when is the last time we signed a big time free agent pitcher? you can't keep trading 4 top prospects for elite pitching, eventually you will have a few good players and no one else on your roster.  

    A Boston team, that returns to it's winning ways AND DOES not fall back into the 2020-2024 trap is one that does both, spends resources on drafting, trading and developing talent but also goes out and take a few big rips. 

    You can convince in any given offseason that a certain set of guys "aren't the guys" but I refuse to accept year after year without any big free agent pitching aquisitions is the way to go. 

    9 hours ago, moonslav59 said:

    Please, no Sale.

    You just know what what will happen, if he comes back.

    Can we please... just once...add a pitcher without so many concerns?

    It's like the Sox have hypnotized us into only being able to see hobbled and broken-down pitchers as options.

    I think it would be the most Red Sox thing ever to have Sale not be very good (injury related) for almost half a decade, go to another team and win a CY Young, and then come back here and either stink or get hurt again. 

    And we'd see the same people who complained about him every day here, then complained about trading him, will complain about trading back for him. 

    I like Sale, I wish we didn't trade him, but he is injury prone and will be 37 next year.  That ship has sailed. 

    9 hours ago, moonslav59 said:

    Please, no Sale.

    You just know what what will happen, if he comes back.

    Can we please... just once...add a pitcher without so many concerns?

    It's like the Sox have hypnotized us into only being able to see hobbled and broken-down pitchers as options.

    I like the "hobbled and broken-down pitchers" as projects, I don't like it when that's all they do.  I liked Buehler so much more last year because they ALSO went out and got Crochet.  Unlike a few years ago when all we got for Christmas was Corey Kluber

    9 hours ago, Larry Cook said:

    What other options are available to us? 
     

    sale’s stuff = Bugatti 

    sale’s body = 1978 ford pinto!!!  But even the pinto occasionally lasted more than 6 months before breaking down!!!! 

    There are plenty of pitchers "available" to us with less concerns than Sale. Sure, there best stuff does not compare in almost all cases, but Buehler had great stuff when healthy and in a groove. Kluber was a multiple Cy Young winner. Richards and Wacha and moments in the sun. Paxton, too. We have one right now in Sandoval. Crawford & Dobbins for 2026. Houck for 2027. We're booked solid.

    I get the fact that anyone can get hurt at anytime, but recent injury history has been a good predictor of what is to come. Even the Sale "success story" saw him miss the ends of both seasons in ATL.

    2 hours ago, Hugh2 said:

    I like the "hobbled and broken-down pitchers" as projects, I don't like it when that's all they do.  I liked Buehler so much more last year because they ALSO went out and got Crochet.  Unlike a few years ago when all we got for Christmas was Corey Kluber

    I'll take back Sale, as long as the cost is not too high AND we also add Ryan, Lodolo or the like. We know better. That ain't happening.

    One could argue we are due to hit gold on a hobbled/broken-down SP'er, soon.

    We have Sandoval, Crawford, Dobbins and Houck, already. Only one will be on the 60 to start the season, so how many 40 man slots do we want to reserve for these types?

    2 minutes ago, moonslav59 said:

    One could argue we are due to hit gold on a hobbled/broken-down SP'er, soon.

    We have Sandoval, Crawford, Dobbins and Houck, already. Only one will be on the 60 to start the season, so how many 40 man slots do we want to reserve for these types?

    I'm done with pitchers over 35 years old.  I don't mind paying for a few years on the back end of a contract if I'm getting a guy in his prime but I don't want to add AARP guys to our staff. 

    4 minutes ago, moonslav59 said:

    One could argue we are due to hit gold on a hobbled/broken-down SP'er, soon.

    We have Sandoval, Crawford, Dobbins and Houck, already. Only one will be on the 60 to start the season, so how many 40 man slots do we want to reserve for these types?

    BTV accepts Kyson Witherspoon and Vaughn Grissom for Chris Sale

    4 minutes ago, Hugh2 said:

    BTV accepts Kyson Witherspoon and Vaughn Grissom for Chris Sale

    If we got Ryan or Lodolo and Sale, I'd be okay with that trade. I'd even give DHam over Grissom, just so Cora can't play him got 300+ PAs.

    16 hours ago, notin said:

    Not all the champions have big name free agent pitchers on long, large deals.

    I only had to go back to the 2023 Texas Rangers.  Eovaldi was on a 3 year deal.  Sure they had deGrom, but he only started 6 games that year.  Technically, they did HAVE the big free agent pitcher in deGrom per your point.  But per mine, they proved they could win without him.

    Also the 2021 Braves, 2017 Astros and 2015 Royals did not have any big free agent pitching contracts…

    Youre actually making good points for both sides of the debate.  Yes the Rangers won without contributions from their big contract pitcher (DeGrom), but this also shows that they were able to overcome all that dead money. Partly becaues these didnt let it stop them from pursuing Eovaldi or other pitchers. Understood it prob made them pause on "large and long" contracts for at least awhile and thats understandable.

    But the point here is that even in your examples of a team winning without a large and long contract for a contributing pitcher, they were still able to overcome the bad contract in DeGrom.

    Im also thinking back to the 90s/2000s Yankees teams where they would seem to always have a bad contract like Kevin Brown or Ellsbury and we would always think woohoo, this is gonna slow them.  And they just went right over it with a speed bump.

    Im not necessarily saying you cant win without a large and long contract for a pitcher or anyone, Im really just saying that when we start talking about how we dont want them, or how they dont help, or how thats the yankees/dodgers way...Well those of us who say that, it feels a lot like towing the company line and I dont lick boots. Not to imply that you or anyone else is actually doing that.  But I like the comment about gotta pay to play. There are exceptions to that rule, for sure.  So maybe you dont HAVE to pay to play, but you are disadvanting yourself considerably by not paying to play.

    And I wonder how much Seager was making when the Rangers won.  Im a dont avoid a bad contract at all costs guy, Im not a you need to have one high paid FA pitcher, that might be a distinction between me and Hughs views, even though I mostly agree and like what Hugh2 is saying.

    48 minutes ago, Hugh2 said:

    I'm done with pitchers over 35 years old.  I don't mind paying for a few years on the back end of a contract if I'm getting a guy in his prime but I don't want to add AARP guys to our staff. 

    Worked with Aroldis…

    2 minutes ago, notin said:

    Worked with Aroldis…

    It was also a one year deal and we didn't have to give up any assets to get him, but yeah I get it.  Some of the old timers can still get it. 

    Aroldis is also a physical freak of a humn being.  

    3 hours ago, Hugh2 said:

    And of those 4 how many are "sustainable winners"? they were all window teams, with the exception of Houston who did seem to extend their window, but they also started paying guys to do that. 

    You've proven that you don't have to be the biggest spender to win, but I never denied that fact, but it's still ALSO a fact that there is a correlation between spending and winning. 

    The Red Sox have the 3rd highest valuation of any mlb team. Last year they had the 5th highest revenue, but if you exlcude NY and LA the other teams were only $10 million more than them. They've been top 5 the past 10 years, and I'd argue that if you take the losing seasons recently out, given Bostons market size we should be the 3rd highest revenue generating team. 

    There is ZERO reason why we can't spend.  We can spend on players, player development, drafting, coaching, scouting etc etc. The point you're proving is that other things add value and create a winning atmosphere as well but when there is an undeniable link between spending and success a fan of the 3rd richest franchise in MLB should demand his club do both. 

    Henry has spent in the past, he thinks he's the smartest guy in the room and tried to go cheap.  I fully expect he has it in him to pivot back and try to do both.  LA is the model to follow, of course we will never be LA, but we never had to be NY to beat NY but we acted pretty darn close to it to get there. 

    I get there is risk, but to me, there is a difference between not spending heavily on free agent pitchers and then practically never spending.  Crochet was a good move, but aside from trades when is the last time we signed a big time free agent pitcher? you can't keep trading 4 top prospects for elite pitching, eventually you will have a few good players and no one else on your roster.  

    A Boston team, that returns to it's winning ways AND DOES not fall back into the 2020-2024 trap is one that does both, spends resources on drafting, trading and developing talent but also goes out and take a few big rips. 

    You can convince in any given offseason that a certain set of guys "aren't the guys" but I refuse to accept year after year without any big free agent pitching aquisitions is the way to go. 

    Bravo, Hugh!

    I especially like the bold.  Not saying be LA or be NY, just saying eat into the payroll gap!

    23 minutes ago, drewski6 said:

    Bravo, Hugh!

    I especially like the bold.  Not saying be LA or be NY, just saying eat into the payroll gap!

    Exactly, when you think about it, we should be somewhere around the 3rd to 4th highest spender yearly.  No reason why you can't do that, dip under the LT every once in a while and occassionally even swing big and out bid LA and NY. 

    3 hours ago, Hugh2 said:

    And of those 4 how many are "sustainable winners"? they were all window teams, with the exception of Houston who did seem to extend their window, but they also started paying guys to do that. 

    You've proven that you don't have to be the biggest spender to win, but I never denied that fact, but it's still ALSO a fact that there is a correlation between spending and winning. 

    The Red Sox have the 3rd highest valuation of any mlb team. Last year they had the 5th highest revenue, but if you exlcude NY and LA the other teams were only $10 million more than them. They've been top 5 the past 10 years, and I'd argue that if you take the losing seasons recently out, given Bostons market size we should be the 3rd highest revenue generating team. 

    There is ZERO reason why we can't spend.  We can spend on players, player development, drafting, coaching, scouting etc etc. The point you're proving is that other things add value and create a winning atmosphere as well but when there is an undeniable link between spending and success a fan of the 3rd richest franchise in MLB should demand his club do both. 

    Henry has spent in the past, he thinks he's the smartest guy in the room and tried to go cheap.  I fully expect he has it in him to pivot back and try to do both.  LA is the model to follow, of course we will never be LA, but we never had to be NY to beat NY but we acted pretty darn close to it to get there. 

    I get there is risk, but to me, there is a difference between not spending heavily on free agent pitchers and then practically never spending.  Crochet was a good move, but aside from trades when is the last time we signed a big time free agent pitcher? you can't keep trading 4 top prospects for elite pitching, eventually you will have a few good players and no one else on your roster.  

    A Boston team, that returns to it's winning ways AND DOES not fall back into the 2020-2024 trap is one that does both, spends resources on drafting, trading and developing talent but also goes out and take a few big rips. 

    You can convince in any given offseason that a certain set of guys "aren't the guys" but I refuse to accept year after year without any big free agent pitching aquisitions is the way to go. 

    So if the Sox traded for Hunter Greene - not a free agent, not a huge contract, not already on the other side of 30 - that would be better, worse or the same as signing, say, Framber Valdez?

    8 hours ago, Hugh2 said:

    It was also a one year deal and we didn't have to give up any assets to get him, but yeah I get it.  Some of the old timers can still get it. 

    Aroldis is also a physical freak of a humn being.  

    Sale has 1 year left on his deal!!!  Allows early and Tolle and Witherspoon more time to develop. 

    1 hour ago, Larry Cook said:

    Sale has 1 year left on his deal!!!  Allows early and Tolle and Witherspoon more time to develop. 

    There are many pitchers with one year left on their deals.

    Also, Sandoval is gone after 2026.




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