Sonny Gray Is the Red Sox Trade Chip Craig Breslow Can't Afford to Get Wrong

[Alex Mayes]

Even after a sweep of the lowly Angels, this Boston Red Sox team is stuck in last place in the AL East and is on the outside looking in at a Wild Card race of mostly .500 teams in front of them. While Alex Spier has reported that the team is likely to wait until after the All-Star Break to make a decision on if they should buy or sell, the timing is right to begin exploring deals for veteran players that can be traded for a haul as the deadline approaches. Obviously, teams are going to call about closer Aroldis Chapman and set-up man Garrett Whitlock, but the ace in the hole for the Red Sox will be none other than Sonny Gray. 

Gray has been the anchor of the starting rotation pretty much all season, even when Garrett Crochet was healthy, so it may seem a bit counterintuitive to trade him when he’s been such an important piece to this team. The rationale behind it is pretty simple though: He’s going to be the second-best starter available on the trade market, behind back-to-back Cy Young winner Tarik Skubal. The Red Sox are going virtually nowhere this year and should have an eye on competing in 2027, whenever that season does get underway in a post-lockout world. Moving on from Gray will allow the team to retool and add pieces who can contribute as soon as next season.

Gray currently holds a 10-1 record over 89.2 innings with a 2.61 ERA, 22.8 K%, 6.4 BB%, 3.6 FIP, and a 1.6 fWAR. He’s been nothing short of elite. He’s worth a great quote at the end of each game and has the type of pitch mix that can play over the next couple of seasons as he gets older. He’s not going to light up the radar gun, but his off-speed and breaking pitches give batters fits on a nightly basis. 

The lone hangup for Gray could potentially be the club option attached to his current contract. In the trade that brought him from St. Louis to Boston, the Cardinals paid down $20 million of the remaining $31 million so, for this season, the team that trades for Gray will only be on the hook for what’s left of the $11 million the Red Sox are paying him. Where it gets tricky though, is next year’s option. Gray’s contract holds a $30 million mutual option with a $10 million buy out. That’s a lot of money on either side of the decision for a 37-year-old. To improve the return, Boston may need to help pay down some of that opt-out money.

The good news is that there are some semi-recent trades of top of the line starters who are in the final year of their contract that we can look to maybe point us in the right direction as to what a return for Gray may look like. Ironically, they both feature former Red Sox players. Let’s turn the clock back to 2014 and 2015.

Trade 1

Boston Red Sox Receive: OF Yoenis Cespedes, 2015 competitive balance draft pick

Oakland A’s Receive: SP Jon Lester, OF Jonny Gomes, Cash considerations

Trade 2

Tigers Receive: LHPs Daniel Norris, Matthew Boyd, Jairo Labourt

Blue Jays Receive: David Price

Let’s start with the trade the Red Sox made. It’s not a direct comparison since Gomes was included in the deal, but there’s a chance there could be a package with a current Red Sox outfielder to get a very similar deal done. The Sox received an All-Star outfielder in Cespedes, who was on the next-to-last year of his contract in 2014. He fit the mold of what the current team is looking for; an offensive force that required opposing pitchers to rethink how they were going to approach the guys in the lineup around him. The Red Sox, even being as far down in the standings as they are, are looking for the impact right-handed bat they were unable to put next to Willson Contreras in the offseason. Using Gray as the centerpiece of a trade could net them that, plus some given today’s improved market for sellers thanks to the introduction of a third Wild Card spot.

Looking at the Price trade, the return was centered around Norris, who was the top overall prospect for the Jays. Labourt was the 13th ranked while Boyd clocked in as the 29th ranked prospect in their system. Turning Price into a number one prospect and two additional top 30 prospects was solid work by Dave Dombrowski, who was promptly fired a few days after the trade. While it’s possible Craig Breslow could be looking at the same fate as Dombrowski in 2015, if he can turn Sonny Gray into a haul of pitchers like Dombrowski did back then, he may extend his stay in Boston by another season. 

Again, the trade market is drastically different now than it was 10+ years ago, but that should mean that Craig Breslow can capitalize even more on Gray’s value as we near the dog days of summer. While the veteran right-hander would be fun to watch through the end of the season here in Boston, the value he brings to such a downtrodden team is being an elite rental starter. There should be no shortage of suitors attempting to pry him out of town.

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[mvp 78]

Trade him before he tweaks something. What are they waiting for? 

[Bellhorn04]

I hate selling!

[mvp 78]

4 minutes ago, Bellhorn04 said:

I hate selling!

You hate a lot of fun things.

[Bellhorn04]

Just now, mvp 78 said:

You hate a lot of fun things.

What other fun things have I expressed hatred for?

[Bellhorn04]

Sonny Gray is a guy that Sox fans have had their eye on as an acquisition for many years.  They finally get him and he's having a brilliant season, but many want to trade him.  I understand the reasons, but it's still a whole heap of suck.

[mvp 78]

7 minutes ago, Bellhorn04 said:

What other fun things have I expressed hatred for?

Making substantial roster adjustments to the team prior to the season in 2022. Umm... 

[mvp 78]

6 minutes ago, Bellhorn04 said:

Sonny Gray is a guy that Sox fans have had their eye on as an acquisition for many years.  They finally get him and he's having a brilliant season, but many want to trade him.  I understand the reasons, but it's still a whole heap of suck.

The heap of suck is just the season and the current trajectory. In order to get out of there, they can't keep doing the same thing (i.e. sticking with the same roster). 

Developing offensive players is too much to ask of this org these days. I think Craig used a wish with a monkey's paw to fix the pitching development and didn't realize what else could happen.

[notin]

For the last two months, Gray gets paid about $11.6mill, $6.7mill of which is covered by the Cardinals.  But St. Louis paid that money to the Red Sox, who do not have to include it with Gray.  Couple that with his buyout, and Gray could be owed up to $21.7 million for two months of pitching, especially since his mutual option (for $30mill) is extremely likely to not get exercised.   
 

If Gray were eligible for a QO, it would just make sense to keep, but Minnesota have him one after 2023.  So in order to get anything decent in return, Boston probably has to include at least $6.7 to $12mill.  Obviously this starts with the Cardinals money, which is a no brainer to include…
 

[Old Red]

1 hour ago, Bellhorn04 said:

I hate selling!

I agree. The Sox are on a upswing, which could make finding that third option in the fork in the road come TDL time more challenging.

[Alex Mayes]

1 hour ago, Bellhorn04 said:

Sonny Gray is a guy that Sox fans have had their eye on as an acquisition for many years.  They finally get him and he's having a brilliant season, but many want to trade him.  I understand the reasons, but it's still a whole heap of suck.

I think not trading him would be the worst decision Craig could make. Even if the Sox are somehow in a position to compete for a Wild Card spot post-deadline, you can survive without Gray if Crochet is headed back and fully healthy. We haven't gotten an info on Early's second opinion yet but, provided it comes back positive, then he will be around as well. 

I like Gray and have watched him pitch for quite a while since I live in Missouri. But he's sitting firmly at the top of the rental starter market and is flirting with ace territory for the rest of this season. Flip him to bolster this roster and the farm system then try to bring him back in the offseason on a two-year deal. That's my ideal path with him.

[Alex Mayes]

4 minutes ago, notin said:

For the last two months, Gray gets paid about $11.6mill, $6.7mill of which is covered by the Cardinals.  But St. Louis paid that money to the Red Sox, who do not have to include it with Gray.  Couple that with his buyout, and Gray could be owed up to $21.7 million for two months of pitching, especially since his mutual option (for $30mill) is extremely likely to not get exercised.   
 

If Gray were eligible for a QO, it would just make sense to keep, but Minnesota have him one after 2023.  So in order to get anything decent in return, Boston probably has to include at least $6.7 to $12mill.  Obviously this starts with the Cardinals money, which is a no brainer to include…
 

The contract is so funky when you dig into it. We disagree that the Sox have to eat money to get anything decent in return for him, but doing so gets an even better return so it's an easy call to make.

[notin]

1 minute ago, Alex Mayes said:

The contract is so funky when you dig into it. We disagree that the Sox have to eat money to get anything decent in return for him, but doing so gets an even better return so it's an easy call to make.

Disagree?

You literally said “To improve the return, Boston may need to help pay down some of that opt-out money.”

So if the Sox include no money and any receiving team is on the hook for the full $21.6mill, you think they get a decent return?

[Duran Is The Man]

1 hour ago, Bellhorn04 said:

Sonny Gray is a guy that Sox fans have had their eye on as an acquisition for many years.  They finally get him and he's having a brilliant season, but many want to trade him.  I understand the reasons, but it's still a whole heap of suck.

i'd rather try to extend him. but that would mean JH would have to spend money, something he seems loathe to do at times.

[mvp 78]

51 minutes ago, Old Red said:

I agree. The Sox are on a upswing, which could make finding that third option in the fork in the road come TDL time more challenging.

Currently 41-48

7/8/24: 49-41

7/8/23: 46-43

7/8/22: 45-38

7/8/19: 49-41

7/8/15: 40-45

7/8/14: 39-50

7/8/12: 43-42

7/8/01: 51-35

7/8/92: 38-42

If 7 games below .500 after July 4th doesn't get you to want to improve your team for next season, enjoy .500 in 2027 I guess. 

 

[mvp 78]

29 minutes ago, Duran Is The Man said:

i'd rather try to extend him. but that would mean JH would have to spend money, something he seems loathe to do at times.

Extend a 36 year old pitcher who has a career low FB velo? No. 

[notin]

33 minutes ago, Duran Is The Man said:

i'd rather try to extend him. but that would mean JH would have to spend money, something he seems loathe to do at times.

SP is the only decent pool in free agency this year, with Skubal, Peralta, King, Woodruff.  And if Skubal and Peralta get dealt in the next 4 weeks, none (including Gray) will be eligible for a QO…

[Alex Mayes]

55 minutes ago, notin said:

Disagree?

You literally said “To improve the return, Boston may need to help pay down some of that opt-out money.”

So if the Sox include no money and any receiving team is on the hook for the full $21.6mill, you think they get a decent return?

 

Yeah, disagree. You said they’d have to eat money to get a decent return, I don’t. I think they should eat money to improve the return, but it’s not necessary to get a decent return back. 
 

The teams that miss out on Skubal will absolutely take on money like that to land Gray. 

[notin]

1 minute ago, Alex Mayes said:

Yeah, disagree. You said they’d have to eat money to get a decent return, I don’t. I think they should eat money to improve the return, but it’s not necessary to get a decent return back. 
 

The teams that miss out on Skubal will absolutely take on money like that to land Gray. 

$21.6 mill for 2 months work limits the trading partners.  I think/hope Boston forwards to St. Louis money, but even then it’s still $15 mill or so, and that’s probably why BTV gives him such a low surplus value.

If no money was included, it would make sense for Boston to hold him, decline the option, and offer a QO because the draft compensation might be better.  But ultimately I think they include the Cardinal money plus some of the buyout and get something with potential…

[Alex Mayes]

Just now, notin said:

$21.6 mill for 2 months work limits the trading partners.  I think/hope Boston forwards to St. Louis money, but even then it’s still $15 mill or so, and that’s probably why BTV gives him such a low surplus value.

If no money was included, it would make sense for Boston to hold him, decline the option, and offer a QO because the draft compensation might be better.  But ultimately I think they include the Cardinal money plus some of the buyout and get something with potential…

We’re in agreement that we think they’ll include money. I just think someone like the Phillies will get real dumb when they miss out on Skubal so there’s a path forward to not eat much of it. I’d rather include the Cardinals money to up the return though. 

[Alex Mayes]

13 minutes ago, mvp 78 said:

Extend a 36 year old pitcher who has a career low FB velo? No. 

I’d bring him back on a low cost, two year deal to act as a mentor to Tolle and Early. Him working with them on their secondary stuff could push both of them to the next level.

[Old Red]

15 minutes ago, mvp 78 said:

Currently 41-48

7/8/24: 49-41

7/8/23: 46-43

7/8/22: 45-38

7/8/19: 49-41

7/8/15: 40-45

7/8/14: 39-50

7/8/12: 43-42

7/8/01: 51-35

7/8/92: 38-42

If 7 games below .500 after July 4th doesn't get you to want to improve your team for next season, enjoy .500 in 2027 I guess. 

 

That fork in the road has been a puzzlement to both Bloom, and Brez has it not?

[mvp 78]

7 minutes ago, notin said:

$21.6 mill for 2 months work limits the trading partners.  I think/hope Boston forwards to St. Louis money, but even then it’s still $15 mill or so, and that’s probably why BTV gives him such a low surplus value.

If no money was included, it would make sense for Boston to hold him, decline the option, and offer a QO because the draft compensation might be better.  But ultimately I think they include the Cardinal money plus some of the buyout and get something with potential…

The problem is that BTV isn't great at deciding what works for a pennant race. When a playoff team needs a #2 like Gray, they aren't going to worry about WAR/$ as much as BTV does. 

[mvp 78]

5 minutes ago, Old Red said:

That fork in the road has been a puzzlement to both Bloom, and Brez has it not?

Seems like a lot of fans on here are equally confused. 

[mvp 78]

5 minutes ago, Alex Mayes said:

I’d bring him back on a low cost, two year deal to act as a mentor to Tolle and Early. Him working with them on their secondary stuff could push both of them to the next level.

I'm not sure that is the deal the other poster was trying to get to TBH. Low cost, two year? Sure. I just think Gray would end up signing for more than you'd want to pay. 

[Alex Mayes]

Just now, mvp 78 said:

I'm not sure that is the deal the other poster was trying to get to TBH. Low cost, two year? Sure. I just think Gray would end up signing for more than you'd want to pay. 

Absolutely, just throwing my thoughts on it into the conversation. I think a team, likely the Cardinals, will end up with him on a two or three  year deal for more money than I’d be comfortable with at his age. 

[Duran Is The Man]

50 minutes ago, mvp 78 said:

Extend a 36 year old pitcher who has a career low FB velo? No. 

then he's doing a helluva job for someone with "career low FB velo".  maybe someone like Jordan Hicks is more to your liking. LOL.

[mvp 78]

1 minute ago, Duran Is The Man said:

then he's doing a helluva job for someone with "career low FB velo".  maybe someone like Jordan Hicks is more to your liking. LOL.

I just wouldn't bet on pitchers above 35 to stay healthy over the course of several years. 

[drewski6]

extend him.  you already have to pay him 10m if he walks. Sooo, that in mind

2 @ 35 each.  70 total.  Its really 60 cuz we are saving the 10m buyout.  He deserves it.  He came home with a last of names.

[drewski6]

1 hour ago, mvp 78 said:

I just wouldn't bet on pitchers above 35 to stay healthy over the course of several years. 

okay, well i ask you this----when you think of jacob degromm in recent years , do you thing about an available workhorse?