Inside The Red Sox

Craig Breslow Makes Surprising Admission On Red Sox's Roman Anthony Negotiations

How did this all come together so quickly?
Jun 18, 2025; Seattle, Washington, USA; Boston Red Sox right fielder Roman Anthony (19) walks to the dugout before  the first inning against the Seattle Mariners at T-Mobile Park. Mandatory Credit: Joe Nicholson-Imagn Images
Jun 18, 2025; Seattle, Washington, USA; Boston Red Sox right fielder Roman Anthony (19) walks to the dugout before the first inning against the Seattle Mariners at T-Mobile Park. Mandatory Credit: Joe Nicholson-Imagn Images | Joe Nicholson-Imagn Images

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The Boston Red Sox's eight-year extension for rookie outfielder Roman Anthony was no small achievement.

Getting a player who nearly everyone believes will be a superstar to buy in for a reasonable price, even with tons of escalators involved that can increase that price, took a fast, decisive effort from Craig Breslow and the Boston front office.

And especially in the wake of last week's trade deadline, pivoting from a disappointing haul to quickly handle the next order of business as a baseball operations department deserves recognition.

How did Craig Breslow, Red Sox negotiate so quickly with Roman Anthony?

Breslow acknowledged in the press conference announcing Anthony's eight-year, $130 million deal that something needed to happen quickly, before the negotiations either became a burden on the youngster's mind or worse, a larger distraction for the team, which has been on fire.

“The balance that we needed to strike was trying to aggressively extend Roman, recognizing how important he is to our 2025 team and also our future without presenting or creating a distraction to a team playing well," Breslow said, per Sean McAdam of MassLive.

“It seems like we successfully struck that balance by putting forth an aggressive offer and being very clear with (Anthony’s agents) that we had no interest in allowing this to become a distraction. If we could work through this quickly, that would be great; and if we couldn’t, that was also OK.”

Then, Breslow revealed that things happened so quickly that within a single day, he went back and forth internally on whether the odds of landing the plane were good.

“It was either going to work or it wasn’t,” said Breslow, per McAdam, “and it was going to have to happen pretty quickly so it didn’t become a distraction on the field.

“Negotiations are so unpredictable that there was a time in the last 24 hours where I thought, ‘This has a real chance of getting done,’ and there were a couple of times in the last 24 hours when I was pretty confident that it wasn’t going to....You have to make years and dollars line up and we were able to do that.”

Whatever Breslow said to Anthony and his agents, it clearly worked. The 21-year-old is locked in for at least three more years than he would have been if he was going to pursue free agency, and it's full steam ahead on making a playoff appearance in year one in the league.


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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org