Article: Aroldis Chapman's Extension is a Gamble, but It's One Worth Taking

[Alex Mayes]

In very unexpected news after a lopsided loss to the Pirates on August 30, the Red Sox agreed on an extension with left-handed closer Aroldis Chapman. Per Chris Cotillo, the extension guarantees Chapman $13.3 million for 2026 with a vesting option for 2027 based on the number of innings he throws next season. He’s getting a raise on his one-year, $10 million contract he signed before the 2025 season, and he’s more than earned it. Through 52 innings pitched, he owns an incredible 1.04 ERA, 1.83 FIP, and 2.2 WAR, to go along with an astronomical 38.7% strikeout rate. He’s almost guaranteed to receive some Cy Young votes and should be the top name in contention for the Mariano Rivera AL Reliever of the Year award. He’s had a career resurgence in Boston, a team that he said he always wanted to play for.

The elephant in the room, though, is that Chapman is 37 and was just extended into his age-38 (and possibly 39) season. Craig Breslow and the front office are gambling a bit with this, but it’s a gamble worth taking if Chapman is even half of the pitcher he has been this season.. 

One of the biggest reasons the Red Sox are confident in this extension is, for the most part, Chapman has been consistently healthy. He’s missed blocks of time throughout his MLB career, but rarely has it been for anything involving his left elbow. He’s been sidelined with shoulder fatigue on occasion, but his elbow has remained steady, even with him still touching 100 mph on the radar gun at 37 years old. There is always concern with pitchers -- especially relievers who go in short, one-inning bursts -- that their elbow could cause them issues at any point, but *knocks on wood* that hasn’t happened so far with Chapman.

This season, he seems to be tunneling his pitches better than he has in years past, and instead of being the wild flamethrower he became known for, he’s mastered his overall command to make his pitch mix play off each other. Opposing hitters can no longer sit on his off-speed pitches and wait for him to throw four balls with his heater like they have in years past because his primary pitches are commanding the strike zone better than ever. Hitters are only making solid contact 10.7% of the time and barreling balls at a 6.8% rate. He’s generating more swing and miss than he has in recent memory. His first pitch strike percentage currently sits at 70.2%, the highest in his career by a fairly large margin. He’s proven that it’s possible to reinvent yourself, even if your overall approach remains the same, late in your career. Coming to Boston seems to have breathed new life into Chapman, so there’s little reason to expect his career to take a drastic nosedive in 2026.

Finally, Chapman originally signed with the Red Sox not knowing if he would be the team’s closer. When he showed up to spring training, there was instant competition for the ninth-inning role, even if looking back on the competitors leaves us with a bad taste in our mouth. Chapman was expected to compete alongside Justin Slaten and, yes, Liam Hendriks for the closer role, with Garrett Whitlock potentially mixing in as well. Even on the Talk Sox Podcast, we discussed how we’d go with anyone over Chapman due to his recent track record in the big leagues and hoped he could ‘find success’ as an eighth-inning set-up man.

You know the story from there. The wheels fell off for Hendriks before he ever could get going, Slaten looked great when splitting closing chances early on but then hit the injured list, and Whitlock stepped into his set-up man role with confidence and poise. As such, the only steady presence in that closer role since spring was Aroldis Chapman. He came into camp as a proven champion as a closer and knew he was going to have to compete with guys to win the role. He shined under the pressure and became the best closer in the American League. Keeping him around for 2026, and possibly for 2027, is a no-brainer simply because he offers a pedigree that was missing from the bullpen for the past few seasons. He’s a winner, a champion, and a leader. Now that he’s anchoring the back-end of the bullpen for another season, he can pass along that wisdom to the next crop of Red Sox relievers.

Even after extending Chapman, there’s still work to be done in the offseason to shore up the bullpen. Having an MVP-caliber closer already in place for next season goes a long way though. Even if Chapman can’t reproduce his incredible 2025 season ever again, he’s still one of the most valuable arms on the roster. When he jogs in from the bullpen, the atmosphere in the stadium changes. You know you’re about to see him reach back and throw gas, then stare down the opposing dugout after he gets a strikeout to end the game. Yes, he’s going to be 38 when this extension kicks in, but he’s proven this season that he could be a couple of steps ahead of Father Time. If he can keep up the pace, this extension could be added to the list of ‘incredibly smart deals by Craig Breslow’ that seems to just keep growing by the week.

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[TedYazPapiMookie]

Great job Breslow!!!

[Nick]

Not sure if I consider this a gamble, essentially a 1 year deal for $13+M.

Buehler signing at $20M was a gamble, signing based solely on his World Series performance.

It's worth the 'gamble'.

[SPLENDIDSPLINTER]

3 hours ago, Nick said:

Not sure if I consider this a gamble, essentially a 1 year deal for $13+M.

Buehler signing at $20M was a gamble, signing based solely on his World Series performance.

It's worth the 'gamble'.

Chapman's lifetime ERA of 2.53 is pretty damn impressive.

[Duran Is The Man]

gamble? i'd call it a sound investment. i'd much rather pay him $13M a year than Hicks. or whatever they're paying Liam Hendricks for absolutely nothing.

[moonslav59]

I felt signing him as the replacement to Jansen was a gamble.

This extension is a no-brainer. I thought he might get $14-15M/1 with a $13M option and $2M buyout, making it a $16M/1 or $28M/2 deal.

Brez is on a roll. While I wish he'd somehow gotten Ryan at the deadline (or Keller) all these extensions and the Devers unload more than make up for it.

The Chapman, Bregman, Narvaez and Crochet winter additions far outweigh the Buehler mistake. (Wilson & Matz outweigh D May.)

Even, last winter looks better with the comeback by Giolito plus adding Slaten, Weissert & Criswell now outweigh the Sale for Grissom trade, IMO.

[SPLENDIDSPLINTER]

1 hour ago, moonslav59 said:

I felt signing him as the replacement to Jansen was a gamble.

This extension is a no-brainer. I thought he might get $14-15M/1 with a $13M option and $2M buyout, making it a $16M/1 or $28M/2 deal.

Brez is on a roll. While I wish he'd somehow gotten Ryan at the deadline (or Keller) all these extensions and the Devers unload more than make up for it.

The Chapman, Bregman, Narvaez and Crochet winter additions far outweigh the Buehler mistake. (Wilson & Matz outweigh D May.)

Even, last winter looks better with the comeback by Giolito plus adding Slaten, Weissert & Criswell now outweigh the Sale for Grissom trade, IMO.

No other contending team's GM got Ryan either. The Twinkies dangled Ryan hoping they'd get an unrealistic offer, an offer they couldn't refuse. It didn't happen. Screw them.

[SPLENDIDSPLINTER]

Just now, SPLENDIDSPLINTER said:

No other contending team's GM got Ryan either. The Twinkies dangled Ryan hoping they'd get an unrealistic offer, an offer they couldn't refuse. It didn't happen. Screw them.

I'm guessing the Pirates were also looking to ask for a ton. No contending team picked up a top shelf starter at the deadline.

[moonslav59]

9 minutes ago, SPLENDIDSPLINTER said:

No other contending team's GM got Ryan either. The Twinkies dangled Ryan hoping they'd get an unrealistic offer, an offer they couldn't refuse. It didn't happen. Screw them.

I think we'll get Ryan, this winter. We have the pieces to offer. It's up to Brez on how much he'll offer.

[moonslav59]

12 minutes ago, SPLENDIDSPLINTER said:

I'm guessing the Pirates were also looking to ask for a ton. No contending team picked up a top shelf starter at the deadline.

Keller's contract is pretty high. He's not as good as Ryan. They are about the same age.

I'd like to see us get both.

Abreu

 Campbell or Garcia

and

2-3 from Clarke, Early, Sandlin, Mullins

Add DHam, Grissom, Wink or Kelly, if wanted.

Maybe sub in Valera or Phillips, if they insist. Romero or Arias are options, but we need to hold our everyday prospects.

Would anyone give Mayer & Clarke or Early for Ryan?

[SPLENDIDSPLINTER]

30 minutes ago, moonslav59 said:

Keller's contract is pretty high. He's not as good as Ryan. They are about the same age.

I'd like to see us get both.

Abreu

 Campbell or Garcia

and

2-3 from Clarke, Early, Sandlin, Mullins

Add DHam, Grissom, Wink or Kelly, if wanted.

Maybe sub in Valera or Phillips, if they insist. Romero or Arias are options, but we need to hold our everyday prospects.

Would anyone give Mayer & Clarke or Early for Ryan?

I'd rather replace Mayer with Abreu.

[moonslav59]

44 minutes ago, SPLENDIDSPLINTER said:

I'd rather replace Mayer with Abreu.

MN might demand Mayer

[TedYazPapiMookie]

4 hours ago, SPLENDIDSPLINTER said:

No other contending team's GM got Ryan either. The Twinkies dangled Ryan hoping they'd get an unrealistic offer, an offer they couldn't refuse. It didn't happen. Screw them.

Ryan is a nice pitcher.  He's not all-star material unless he's playing for a bad franchise and he's clearly not elite with his numbers so why waste prospects on him?  The team now has Crochet, Tolle, Giolito and Bello who are all looking better than the 29-year-old Ryan.  Is he better than May?  Probably but May might start improving working with the Breslow staff of pitching coaches.  Also, they have both Houck and Kutter coming back under control as potential #5 SPs not to mention the upside potential of Witherspoon and other recent farm hands that have been added in the last two years.  The pitching is now deep enough to withstand injuries unlike in the past.  That's all a credit to Breslow.

Also, Miami has many young stars that might be cheaper so let Breslow's group analyze their potential before considering slightly above average pitchers like Ryan.  

[moonslav59]

25 minutes ago, TedYazPapiMookie said:

Ryan is a nice pitcher.  He's not all-star material unless he's playing for a bad franchise and he's clearly not elite with his numbers so why waste prospects on him?  The team now has Crochet, Tolle, Giolito and Bello who are all looking better than the 29-year-old Ryan.  Is he better than May?  Probably but May might start improving working with the Breslow staff of pitching coaches.  Also, they have both Houck and Kutter coming back under control as potential #5 SPs not to mention the upside potential of Witherspoon and other recent farm hands that have been added in the last two years.  The pitching is now deep enough to withstand injuries unlike in the past.  That's all a credit to Breslow.

Also, Miami has many young stars that might be cheaper so let Breslow's group analyze their potential before considering slightly above average pitchers like Ryan.  

Houck is out until 2027.

Giolito will likely be a FA.

Crawford may be back and may be in the pen or a 5th starter- maybe.

Witherspoon may not rise as fast as Tolle. 2027 might be too soon to expect him.

Ryan is tied for 14th in fWAR- a clear All Star caliber pitcher and an ACE on 18-20 teams. He's 20th in ERA and 21st in ERA-. He's 17th in xFIP. Those numbers are better than Bello and better than 2024's Houck.

If you trust Brez, then trust there was a reason he tried to get Ryan at the deadline.

[cp176]

It would be nice for sure to add another frontline starting pitcher.  I’m just hoping that the Sox don’t overpay for something that really isn’t a seriously pressing issue.  Sign Bregman, sign Giolito, go after a legit power bat to replace Yoshida and then listen to what teams have to offer in trade for pitching.  Don’t overpay., 

[moonslav59]

6 hours ago, cp176 said:

It would be nice for sure to add another frontline starting pitcher.  I’m just hoping that the Sox don’t overpay for something that really isn’t a seriously pressing issue.  Sign Bregman, sign Giolito, go after a legit power bat to replace Yoshida and then listen to what teams have to offer in trade for pitching.  Don’t overpay., 

If it's not a pressing issue, then why mention signing Giolito?

We will go into 2026 with only Crochet & Bello as sure bets to be ready and good starters.

IMO, we need Giolito and a Ryan type. I'd settle on Keller. Since I doubt we spend large and long on a FA pitcher, and I'm not super thrilled about Cease, King or Framber, I think a trade is in the winter plan.

It will likely have to be an overpay, since all deals for proven SP'ers with 2 years of control seem to be, when made, but I do agree we should no grossly overpay for one.

Our OF depth seems like the likely spot to centerpiece the suggested trades:

Anthony, Rafaela, Duran & Abreu

Campbell, Jh Garcia, Refsnyder (retire?) & Yoshida

Far away: J Gonzales, Taylor, YRod & Bleis, then Azocar, Rivas, Fermin & Turner/Martin

I like the idea of moving Casas to DH. He sucks at 1B and is injury prone. If that happens, it takes up a slot from our 4th and 5th defensive OF'er depth chart (Duran/Campbell/Garcia)

I'll be shocked, if we don't trade an OF'er to fill another great need like SP 2/3 or 1B/2B.

[cp176]

7 hours ago, moonslav59 said:

If it's not a pressing issue, then why mention signing Giolito?

We will go into 2026 with only Crochet & Bello as sure bets to be ready and good starters.

IMO, we need Giolito and a Ryan type. I'd settle on Keller. Since I doubt we spend large and long on a FA pitcher, and I'm not super thrilled about Cease, King or Framber, I think a trade is in the winter plan.

It will likely have to be an overpay, since all deals for proven SP'ers with 2 years of control seem to be, when made, but I do agree we should no grossly overpay for one.

Our OF depth seems like the likely spot to centerpiece the suggested trades:

Anthony, Rafaela, Duran & Abreu

Campbell, Jh Garcia, Refsnyder (retire?) & Yoshida

Far away: J Gonzales, Taylor, YRod & Bleis, then Azocar, Rivas, Fermin & Turner/Martin

I like the idea of moving Casas to DH. He sucks at 1B and is injury prone. If that happens, it takes up a slot from our 4th and 5th defensive OF'er depth chart (Duran/Campbell/Garcia)

I'll be shocked, if we don't trade an OF'er to fill another great need like SP 2/3 or 1B/2B.

I mentioned Giolito because I think that that is a no brainer type of decision.  He’s here, we sign him.  Starting pitching of course becomes a big issue if he is not signed.  Crochet, Bello, Giolito, Tolle, Dobbins, probably Crawford, maybe May -  I would sign the big bat before I’d go after anyone else.  If a trade could be done for a top of the line starter whoever he may be, I guess so but I wouldn’t overpay.  The team is in a position of strength.  

[Deja Doh]

Gamble.  That's what two Guardian players do (allegedly).  The guy has a 1.00 ERA.  Anything sub 4.00 is considered decent.  

[moonslav59]

19 minutes ago, cp176 said:

I mentioned Giolito because I think that that is a no brainer type of decision.  He’s here, we sign him.  Starting pitching of course becomes a big issue if he is not signed.  Crochet, Bello, Giolito, Tolle, Dobbins, probably Crawford, maybe May -  I would sign the big bat before I’d go after anyone else.  If a trade could be done for a top of the line starter whoever he may be, I guess so but I wouldn’t overpay.  The team is in a position of strength.  

To me, in order to be a legitimate top contender, we need 2 solid SP'ers (Gio can be one of them) and a big bat (1B, DH or 2B seem like the most logical positions.) This assumes Bregman returns.

Gio, Ryan & Alonso is the dream.

The reality might be Gio, Keller and a Lowe return.

[cp176]

10 hours ago, moonslav59 said:

To me, in order to be a legitimate top contender, we need 2 solid SP'ers (Gio can be one of them) and a big bat (1B, DH or 2B seem like the most logical positions.) This assumes Bregman returns.

Gio, Ryan & Alonso is the dream.

The reality might be Gio, Keller and a Lowe return.

Agree - After being there yesterday, I can’t imagine Durran being used in any sort of trade though.  Maybe I guess, but it could cause a massive mutiny.  When he came up to pinch hit, the decibel level was turned up to a huge volume.  He’s a huge favorite.

[cp176]

As for second base, think I’m still going to go with Mayer taking over there.  His injury history is a concern, but he is too young and potentially too good to ship out just yet.  A big bat to either play first(someone not named Casas) or dh is definitely needed I think.  Another solid number two to go along with what we already have would get me back into the park on a regular basis.  I just don’t want to see us burned on another lopsided trade deal.  The Sox should be dealing from a position of strength.  

[moonslav59]

1 hour ago, cp176 said:

Agree - After being there yesterday, I can’t imagine Durran being used in any sort of trade though.  Maybe I guess, but it could cause a massive mutiny.  When he came up to pinch hit, the decibel level was turned up to a huge volume.  He’s a huge favorite.

MN probably prefers the longer team control of Abreu over Duran, anyway.

[moonslav59]

1 hour ago, cp176 said:

As for second base, think I’m still going to go with Mayer taking over there.  His injury history is a concern, but he is too young and potentially too good to ship out just yet.  A big bat to either play first(someone not named Casas) or dh is definitely needed I think.  Another solid number two to go along with what we already have would get me back into the park on a regular basis.  I just don’t want to see us burned on another lopsided trade deal.  The Sox should be dealing from a position of strength.  

The last major deal was Crochet, and that is the type of deal I'd like to see one more of- not the sell-off Betts deal, not the sell-off Sale deal, although that one does not look as bas as before with the money saved used for Gio, who is now doing very well.

I think we can trade Abreu, Campbell and 2 from Clarke, Early, Sandlin & Mullins and get a stud pitcher plus another piece.

[drewski6]

On 8/31/2025 at 8:11 PM, moonslav59 said:

Keller's contract is pretty high. He's not as good as Ryan. They are about the same age.

I'd like to see us get both.

Abreu

 Campbell or Garcia

and

2-3 from Clarke, Early, Sandlin, Mullins

Add DHam, Grissom, Wink or Kelly, if wanted.

Maybe sub in Valera or Phillips, if they insist. Romero or Arias are options, but we need to hold our everyday prospects.

Would anyone give Mayer & Clarke or Early for Ryan?

Mayer and Clarke/Early all freaking day. Would even consider all 3.

Youd prefer Keller to Gio? Something to be said for having shown you can pitch in the AL East, right?

Keller good fallback if someone pays Gio through the nose, but I would prefer to try to bring back Gio.

[drewski6]

17 hours ago, cp176 said:

I mentioned Giolito because I think that that is a no brainer type of decision.  He’s here, we sign him.  Starting pitching of course becomes a big issue if he is not signed.  Crochet, Bello, Giolito, Tolle, Dobbins, probably Crawford, maybe May -  I would sign the big bat before I’d go after anyone else.  If a trade could be done for a top of the line starter whoever he may be, I guess so but I wouldn’t overpay.  The team is in a position of strength.  

Its a no brainer assuming someone doesnt come in an offer him a 6 yr contract at 20m+ per

[drewski6]

5 hours ago, moonslav59 said:

The last major deal was Crochet, and that is the type of deal I'd like to see one more of- not the sell-off Betts deal, not the sell-off Sale deal, although that one does not look as bas as before with the money saved used for Gio, who is now doing very well.

I think we can trade Abreu, Campbell and 2 from Clarke, Early, Sandlin & Mullins and get a stud pitcher plus another piece.

I wouldnt trade Abreu, but Id get over it if they turned around and got a real power hitter + kept Breg

Youd have Breg, Duran, RA, and new power hitter in your top 4. 

[moonslav59]

1 hour ago, drewski6 said:

Mayer and Clarke/Early all freaking day. Would even consider all 3.

Youd prefer Keller to Gio? Something to be said for having shown you can pitch in the AL East, right?

Keller good fallback if someone pays Gio through the nose, but I would prefer to try to bring back Gio.

I'd take Gio over Keller, but quite frankly, I'd like to see this as our opening day rotation:

Crochet

Ryan

Bello

Giolito

Keller

The rest can be depth or work from the pen, where we need depth.

[moonslav59]

Just now, moonslav59 said:

I'd take Gio over Keller, but quite frankly, I'd like to see this as our opening day rotation:

Crochet

Ryan

Bello

Giolito

Keller

The rest can be depth or work from the pen, where we need depth.

I hesitate to trade a 2B option, when 2B (and SS/3B depth) ar4e concerns more than OF depth is.

 

[moonslav59]

2 hours ago, drewski6 said:

I wouldnt trade Abreu, but Id get over it if they turned around and got a real power hitter + kept Breg

Youd have Breg, Duran, RA, and new power hitter in your top 4. 

So, you'd trade Rafaela or play him at 2B?

Tade Antony or have an OF'er ride the bench every game?

[mvp 78]

1 hour ago, moonslav59 said:

I'd take Gio over Keller, but quite frankly, I'd like to see this as our opening day rotation:

Crochet

Ryan

Bello

Giolito

Keller

The rest can be depth or work from the pen, where we need depth.

They aren't going to be able to invest that much on the rotation unless they are having someone take on Masa's full salary. Why block a cheap Tolle for a mediocre Keller that would cost a decent return in trade?