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

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.