In Roman Anthony talks, Red Sox went back for seconds with ‘aggressive offer’ to close deal

BOSTON — When the Major League Baseball trade deadline arrived last Thursday at 6 p.m., Red Sox chief baseball officer Craig Breslow intuitively understood that his work was far from done.

The deadline signaled the end of any deals being made between clubs, but for an executive with a contending team, the work never ends.

And so it was that Breslow quickly pivoted to the next task at hand: namely, getting Roman Anthony to sign off on a long-term contract extension.

“We don’t ever truly have a chance to catch our breath,” joked Breslow of the baseball calendar. “I think what we do is just shift priorities from one thing to another. I guess the beauty of the trade deadline is that it is a true, rigid deadline. And once it passes, we can comfortably shift our priorities to other things and I wanted to strike up these conversations immediately.”

The Red Sox had approached Anthony in spring training, hoping to lock him up as they had done with Brayan Bello and Ceddanne Rafaela the spring before, and as they were about to do with Kristian Campbell.

At the time, the notion of an extension wasn’t appealing enough to Anthony. He had yet to play a game in the big leagues, hadn’t been exposed to Boston and was unsure what to expect.

But after being promoted in June, Anthony’s interest in getting a deal done grew, and though the first week of August is hardly a typical time to work through complicated contract extensions, Breslow was determined to give it a try.

“It was the responsible decision in my view,” Breslow noted. “This was someone we were willing to invest in.”

In the span of two months, Anthony showed why had he been tabbed as the best prospect in the game. Following a somewhat uneven start, Anthony had compiled an .823 OPS with the Red Sox while grading out as a well-above average defender in the outfield.

Still, the 159 at-bats that Anthony compiled didn’t fundamentally change the Red Sox’ projections for Anthony; they merely validated them.

“This was someone for whom we always had really, really high expectations,” Breslow said. “We had all the confidence in the world, just seeing how Roman had worked his way through the system, the presence and interactions he had in spring training, the way that he performed in his first major league spring training to believe that there was a long, successful career ahead of him.”

So, Breslow went to work.

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

“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.”

In a brief conversation with Breslow, Anthony expressed how he had grown to enjoy the city of Boston and how he relished playing in front of the team’s fan base.

“He was very clear what he wanted to do,” said Alex Cora. “He loves it here. He works hard. He wants to win here. That’s something he told me (Tuesday night) — ‘Here’s what’s going on, here’s what’s going to happen, and the reason is that I love it here.’ “

A deal was struck quickly thereafter, though given the amount of money involved, there were some uncertain moments for both sides.

“It was either going to work or it wasn’t,” said Breslow, “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.”

Ultimately, the sides came together, and Anthony was able to arrange for his parents, brother and sister to be on hand for the announcement, held some 90 minutes or so before Wednesday’s first pitch.