Examining Craig Breslow's Bizarre, Ugly Handling of a Robust Bullpen Market

The trade deadline for the Boston Red Sox was filled with… meh. I’ll be the first to say that I like the Dustin May deal on the surface, especially if they re-sign him, but the Matz deal doesn’t do a ton for me seeing what else the Cardinals shipped out. Phil Maton would make more sense as a right-handed reliever, and if they were set on a left-handed reliever, then they should have paid a higher asking price for JoJo Romero. Take it one step further, and Ryan Helsley would have given the Red Sox an opportunity to make far bigger splashes in the trade market as other relievers would have become expendable. The issue here, though, is that Craig Breslow failed to capitalize on an incredibly favorable market for sellers.

The Red Sox operated on the fringes of the trade market until a last minute push for Joe Ryan, which Ken Rosenthal called ‘feeble at best’, signaling that Breslow was unwilling to play in the deep-end of the trade pool. Look, that’s okay if that’s the lane you’ve fully committed the team to. But, of the front office didn’t believe that this team was worth actually investing in, then you needed to pick a different path. Why bring in a fifth left-handed reliever when you could have traded the ones you already have for pieces that could actually net you what you were looking for?

I’ve been adamant that the Sox needed to move on from Aroldis Chapman at the deadline because of how rare it is for a reliever at his age to be this dominant. Then, the Phillies went crazy for Jhoan Duran and the Padres, in typical A.J. Preller fashion, lost their minds for Mason Miller. Once Helsley, Duran, and Miller were off the board, Breslow should have pivoted to Chapman and started a bidding war for teams that were in on all of those names. The Dodgers were in on Duran and likely would have paid more than Dustin May for Chapman had Breslow made him available. I’m not claiming that Chapman is on the same tier as Duran and Miller—he’s a rental and they are younger and have far more control— but it's clear the market would have ponied up big time for a guy with a 1.29 ERA and 19 saves.

And, if you really believe that Chapman is too instrumental to this team' success to lose, then why not deal Justin Wilson, your other rental left-handed reliever? Why bring in a third rental southpaw reliever at all? That Matz trade truly felt like the team making a move for the sake of making a move, and if Blaze Jordan was the price for a rental reliever with a 3.44 ERA, imagine what Wilson and his 2.65 ERA (and far cheaper contract) could have pulled in on the open market. This truly just felt like a directionless trade deadline.

Craig Breslow’s tenure with the Boston Red Sox has been marked by incredibly high moments (trading for and then extending Garrett Crochet and signing Alex Bregman), but also two less-than-lackluster trade deadlines. If Breslow wasn’t comfortable playing in the big pool of the trade market, then he had the assets to take advantage of a market that was wanting for more sellers. The other three contenders in the AL East all got better at the deadline, and the teams surrounding the Red Sox in the Wild Card race got better as well. The Red Sox mostly sat on their hands and hoped something would fall into their lap. Breslow seems to be most comfortable operating when he’s not up against a deadline and during the offseason, which is fine. But if he can’t navigate the trade deadline, he’s never going to be an effective President of Baseball Operations, especially for a large-market team like the Red Sox.