With 48 hours or so having elapsed since the Boston Red Sox finalized a trade for Sonny Gray, fans are interested in how the trade went down. When did negotiations begin? How long have the Red Sox been eyeing Gray? Appearing as a guest on MLB Network on Wednesday, The Athletic‘s Red Sox insider Jen McCaffrey was able to answer many of these questions about Boston’s pursuit of Gray. McCaffrey revealed the the Red Sox as a franchise have actually been interested in Gray dating back to the 2011 MLB Draft, when Boston was interested in selecting Gray. The second thing that McCaffrey noted was that Boston’s current front office — headlined by chief baseball officer Craig Breslow — places a priority on pitchers who can strike people out at a high rate. This attracted Breslow and Co. to Gray, according to McCaffrey, especially because the Red Sox only have one pitcher in 2025 tally 200 strikeouts (Cy Young runner-up Garrett Crochet). Story continues below advertisement McCaffrey also said that the Red Sox like Gray’s durability, pointing to the fact that he’s made 24 or more starts in every season since 2019. Boston also liked the idea of adding Gray on a one-year deal, as this doesn’t get in the way of the development of some of their young pitching talent moving forward. According to McCaffrey, discussions between the Red Sox and the St. Louis Cardinals picked up near or shortly after the end of the MLB regular season, at which point Gray had publicly made clear that he’d waive his no-trade clause for the right opportunity. McCaffrey said that the Red Sox and Cardinals started putting their heads together and talking about a potential deal. Talk proceeded slowly, but picked up once Richard Fitts and Brandon Clarke became the agreed-upon player capital headed to St. Louis in the deal. From that point, it was up to the Cardinals to restructure the trade a bit (via sending Boston significant cash) to make it all work for both sides. Story continues below advertisement