Red Sox Coach May Have Played a Surprise Role in Rafael Devers Trade

It’s possible that Red Sox pitching coach Andrew Bailey could have been involved with the return of players from the Rafael Devers trade.
Boston Red Sox v Seattle Mariners
Boston Red Sox v Seattle Mariners | Maddie Malhotra/Boston Red Sox/GettyImages

The Boston Red Sox raised many eyebrows and dropped many jaws with their decision to trade the best bat in their lineup and the face of the franchise in Rafael Devers, to the San Francisco Giants after less than two years into a 10-year commitment.

The return for Devers, a two-time Silver Slugger, a three-time All-Star, and a World Series Champion, was unbalanced and another example of Boston’s organizational malpractice from the front office.

In return for Devers, Boston received three pitchers in Kyle Harrison, Jordan Hicks, and Jose Bello, and an outfield prospect with James Tibbs III, the 13th-overall pick in the 2024 MLB Draft and the No. 4 prospect in the Giants organization.

Although Boston received some high-end younger talent in the deal, San Francisco accepted to take on the full balance remaining on Devers’ contract that still has $250 million over the next eight and a half years owed to him. 

It became important for Boston to find a team that would take on the full contract so that they wouldn’t be responsible for paying Devers any further, which made this into a true salary dump for the Red Sox, something that a big market team shouldn’t have to be worrying about.

The timing of the trade also didn’t make any sense, as the Red Sox were on a winning streak and climbed their way back into a playoff scenario in the American League. Boston also could have received a better return if they had made the trade closer to the trade deadline or in the offseason.

So why did the Red Sox make this trade now with the Giants?

Red Sox Pitching Coach May Be Surprise X-Factor in Rafael Devers Trade

I believe there’s another connection here that isn’t being looked at enough, and it’s with pitching coach Andrew Bailey, who may have played a part in the return for Devers from San Francisco.

Before Bailey became the pitching coach in Boston, he was the pitching coach in San Francisco from 2020 to 2023, where he was credited for improving their pitchers overall and became one of the most coveted pitching coaches in the league.

During his time with San Francisco, Bailey likely played a part in the scouting and development of Harrison and Bello, who the Red Sox acquired from the trade for Devers.

I’m not saying Bailey orchestrated the deal, but as starting pitching is a position that Boston wants to improve on, it’s not a coincidence to have Bailey’s suggestions on players he’s probably scouted and worked with not so long ago.

Harrison was drafted in the third round of the 2020 MLB Draft while Bello was signed in 2023 at just 17 years old as an international free agent out of the Dominican Republic. It’s hard to believe that Bailey wasn’t involved with the scouting of these players as the head pitching coach.

On Tuesday in Seattle, NESN’s Jahmai Webster had a chat with Bailey on what Harrison can bring to the table for Boston:

“Love Harry, he's an awesome, great person first and foremost. For a young guy, being drafted at an early age like that, total pro, surrounds himself with the right people. Goes about work the right way, fire competitor, wants the ball every fifth day. Red Sox Nation will grow to love him and I’m excited to have the opportunity to watch him compete, to work with him, watch him continue to grow into a superstar in this league.”

Bailey has a firm grasp on his intentions with the pitchers and designing programs to help further the development of his players. 

If San Francisco was the only team Boston wanted to play with for a trade partner, I have to trust that if Bailey was involved, then the Red Sox did acquire some really good talent that will hopefully pan out in the near future.

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