It was the worst kept secret in baseball that the Red Sox and White Sox were spent plenty of time leading up to the deadline trying to work out a trade that would send Chris Sale or Jose Quintana to Boston. No deal would ever materialize, however, and now Jon Heyman says that Jackie Bradley Jr. was, effectively, the deal breaker:
The issue appears to be Chicago's insistence on one of Boston's current young stars (along with a package of prospects).
"If they didn't get Jackie Bradley, there was no way they were doing the deal," one person familiar with their thinking said.
In the month following the non-trade, Bradley has been dealing with his first really bad stretch of the year since he hit .222/.271/.315 in the first weeks of April. Still, it's not hard to see why the Red Sox were reluctant to include Bradley. By the estimations of both Fangraphs and Baseball-Reference, JBJ has been worth between four and five wins to the Red Sox this season, and should finish somewhere above the latter number unless he continues to slump hard for the rest of the season.
For context, that leaves Bradley as the third most valuable position player on the Red Sox behind Betts and Pedroia, and in the upper echelon of outfielders in the game.
Obviously, the price for a Sale or Quintana was always going to be high, but reputation and a longer track record are the only things that would keep Bradley-for-Sale (or Quintana) from being seen as a reasonable 1-for-1 deal. Based only on their play in 2016, neither is clearly more valuable than the other. Then you start throwing prospects in, and looking at contract situations, where Bradley is under team control for longer at a lower cost?
Certainly the White Sox were well within their rights to ask for the world here, and given Sale's reputation as one of the game's best young arms and a legitimate ace, it makes sense that they did so. But even taking all the bad of the first and last month, Bradley has emerged as one of the game's best young position players. And while the Red Sox might've needed a pitcher more than an outfielder at the time, when you consider the other names the White Sox might have asked for in addition to Bradley, it also makes sense that the Red Sox balked.