So it caught Rodgers off guard when Breslow informed the agent that he’d just sent a new contract proposal to Rodgers and Anthony. Had Breslow only sent it to Rodgers, the agent might have stiff-armed the request.
But Anthony — who’d been alerted Sunday morning by Sox principal owner (and Globe owner) John Henry that the team was preparing to make him another offer — had opened the email, and greeted it with immediate enthusiasm, which he relayed to Rodgers.
Get Starting Point
A guide through the most important stories of the morning, delivered Monday through Friday.
There had been a considerable gap in talks between the sides in spring training. Though the distance had narrowed over three offers by the Sox, the conversations had never gotten close enough to a deal to produce true back-and-forth about a framework.
There was no enmity — “The main goal [of a long-term deal] had been the same,” Anthony said of the sides’ positions — but there’d been comfort in the fact that Anthony would direct all his attention to the field in 2025.
Then, the Sox came back with a different proposal on Sunday.
“Definitely a little bit surprised,” Anthony said of the team’s efforts to renew talks. “I don’t think you ever expect something like that. But for me, it was just excitement seeing what it was, knowing what I value myself at, and seeing that initial offer [on Sunday], I could say, ‘Wow, this is exciting.’ . . . It was exciting that we were trending in the right direction.”
Moreover, Anthony was coming at talks from a different vantage point than the spring. At that point, he was the top prospect in the game but had yet to make his big league debut or experience playing at Fenway. He didn’t know what life was like inside the close-knit Red Sox clubhouse.
“This is a place that I want to be,” said Anthony. “There was no doubt about it.”
Breslow and the Sox, days removed from the trade deadline, recognized there was an element of risk in trying to rekindle talks. As a former Red Sox player, Breslow had watched in-season talks about long-term deals both come together and add to clubhouse closeness (Dustin Pedroia in 2013), and also had seen the collapse of talks become a distraction to a team and player (Jon Lester in 2014).
Still, with the benefit of nearly two months to see Anthony at the big league level, the team recognized a special talent who had rapidly established himself as a franchise pillar. The Sox wanted to formalize that status for years to come — and decided to do so as soon as possible after the deadline.
“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 we wanted to kind of strike up these conversations immediately,” said Breslow. “The balance that we needed to strike was trying to aggressively extend Rome and recognizing how important he is to our 2025 team and also our future with not presenting or creating a distraction when this team is playing so well . . . [The Sox were] very clear with Mark and Roman’s camp that we had no interest in allowing this to become a distraction, and that if we could work through this quickly, that would be great, and if not, that was also OK.”
And so, Rodgers and Breslow — who’d known each other for years, dating to when another Rodgers client, Andrew Miller, was Breslow’s teammate with the Red Sox from 2012-14 — started discussions, working through the night. Everyone was willing to consider the matter for a narrow window of perhaps a few days.
Talks continued Monday — a day when Anthony was a late scratch because of tightness in his back. Was it helpful to be able to concentrate on the talks rather than to worry about taking them to the field?
“It was the opposite,” said Anthony. “When I take the field, my mind is clear. I’m out there and trying to win a game.”
Even so, talks advanced far enough Monday that Rodgers and his colleague at Frontline, Stephen Young, made plans to fly to Boston for face-to-face meetings. (A third Frontline agent, Matt Rodriguez, already happened to be in Boston for the Red Sox-Royals series.) The sides had entered a back-and-forth stage that had to account for a number of elements, including:
▪ Past precedents of top young players who signed long-term deals, notably including the eight-year, $111 million deal Corbin Carroll signed with the Diamondbacks.
▪ The potential that a top-two finish in Rookie of the Year voting would result in Anthony being granted a full year of service time for 2025, potentially making him eligible for free agency by the end of 2030.
▪ How to reward Anthony if he emerged as one of the top players in the game.
The sides met in-person twice Tuesday, with Breslow and assistant GM Paul Toboni — who was the team’s amateur scouting director in 2022 and made Anthony a second-round pick — speaking on behalf of the Sox.
At the first meeting, which took place prior to Tuesday’s game, there was progress but still elements to overcome. The contract could feature escalators based on Anthony’s potential finishes in Rookie of the Year and MVP voting, as well as All-Star selections to reward the outfielder in the potential free agent seasons that the Sox would be buying out.
Rodgers and his colleagues left the park and worked nearby at Eastern Standard, waiting for a proposal. Finally, the proposal came — still not good enough for Anthony’s agents. The sides reconvened at Fenway late in the game.
At that point, there was mostly agreement on a larger framework, but they wrestled on some of the details — the sort of elements that can derail a conversation. Among the last ones: Rodgers and Frontline didn’t want to accept a buy-out of an option for 2034 as “guaranteed” money that would come at the expense of what Anthony might earn. They wanted the opt-out to be guaranteed.
The issue became a sticking point. Rodgers and the Frontline team, in fact, started walking out of Fenway.
“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,” Breslow said on Wednesday afternoon. “And there were multiple times in the last 24 hours where I was pretty confident that it wasn’t going to.”
But Breslow and the Sox worked past each potential sticking point. As Rodgers and his group walked down the street, Breslow called and asked for a few minutes to approach team owners about the request to guarantee the buyout money in the opt-out.
The request was greenlit. At roughly 10:30 or 11 p.m., the sides had reached an agreement on an eight-year deal running from 2026-33 that guarantees Anthony $130 million, with a $30 million team option for the 2034 season. Escalators could boost the deal by as much as an additional $70 million, creating potential earnings of $230 million.
Rodgers called Anthony to share the good news — and to let him know he’d need an early wake-up to take a physical to make the contract official. By Wednesday afternoon, the results of the physical were in. Anthony, summoned by a team trainer, jogged off the field to sign a contract that he and the Sox hope is life-changing for the player and the organization.
Anthony recognizes that in signing a long-term deal, there’s a possibility he left potential earnings on the table. He doesn’t care — or at least, doesn’t care as much as he does about the opportunity that the contract represents: A number that rewards him as a top young talent and gives him a chance to play where he wants, with the team he wants, for the fans he wants.
“This is a number I’m completely satisfied with, along with my family and agency,” said Anthony. “Why wouldn’t I want to do this? I’m not worried about what I could earn or potential earnings down the road if I keep doing what I’m doing. That’s not the way I look at it. I don’t live life like that. I live life knowing that this is plenty and this is where I want to be. It’s as simple as that.
“I’ve never gone out thinking, ‘Hey, I’m playing for a contract. I’m playing for money.’ I don’t play this game for money. I play this game because I love it, and I want to win, and I want to win in Boston.”
Alex Speier can be reached at alex.speier@globe.com. Follow him @alexspeier.