
The Boston Red Sox have been busy this offseason, swinging big trades for Sonny Gray, Johan Oviedo and Willson Contreras. They’ve also spent big in free agency, signing Ranger Suarez to a five-year, $130 million deal.
While Craig Breslow has made several bold moves this winter, the offseason has also brought its share of frustration for the Red Sox. They lost Alex Bregman to the Chicago Cubs and were shockingly the last Major League team to sign an MLB free agent.
Other deals have fallen through as well, leading Breslow to open up about Boston’s recent near misses during Suarez’s introductory press conference at Fenway Park on Wednesday.
“There are moments over the course of the offseason where you feel like you’re minutes away from a trade coming together and signing, and then you look up a couple hours later and the whole thing dissolves,” Breslow told reporters.
“I think we’ve been pushing all offseason trying to have as many conversations as we can,” Breslow continued. “And, you know, if it’s free agency, it’s getting uncomfortable. If it’s trades that are putting guys in the conversation, we would much prefer to hold on to them.”
To Breslow’s point, making deals is difficult. Free agency often involves outbidding other teams for the same player, while trades require giving up valuable assets to get something in return.
It’s notable, and perhaps telling, that Breslow’s two biggest free-agent signings so far — Bregman and Suarez — both came late in the winter. This year, the Suarez signing happened after the Red Sox had already missed out on Bregman, Pete Alonso and other big names.
Breslow was aggressive in the trade market early in the offseason, acquiring Gray and Oviedo before the Winter Meetings. He may need to move a little quicker in free agency, however, if he wants to land his top free-agent targets going forward.







