Inside the Red Sox courtship of Rafael Devers, from the Santo Domingo dinner to the final deal

Eleven days before Christmas, all of the fancy restaurants in the Dominican Republic capital of Santo Domingo must have been booked solid, because the Red Sox called more than two dozen and not one could accommodate a large private party on such late notice. When someone finally called the InterContinental Real Santo Domingo, the staff agreed to close a portion of the hotel to the public for a clandestine meeting so that the Red Sox could quietly offer Rafael Devers the largest contract in franchise history.

Although the club had been in negotiations with Devers since the spring of 2021, the urgency of a long-term deal had peaked the previous week when Xander Bogaerts agreed to an 11-year deal with the Padres. At that point, Devers became the team’s top priority, and members of the baseball operations department suggested to owner John Henry that his presence at an in-person meeting with Devers would go a long way in the eyes of the third baseman.

Henry offered not only his attendance, but also his private plane.

And his checkbook.

On the morning of Dec. 14 — the day after a press conference introducing new closer Kenley Jansen, and the day before another introducing new outfielder Masataka Yoshida — Henry flew to Santo Domingo with Red Sox president Sam Kennedy, chief baseball officer Chaim Bloom, general manager Brian O’Halloran and assistant general manager Eddie Romero. The group was joined by manager Alex Cora, who flew separately from Puerto Rico. At 3 pm, the group met with Devers and his agent, Nelson Montes de Oca, plus three of the highest-ranking executives at REP 1 baseball sports agency. In their closed-off section of the InterContinental, the staff served their unexpected guests appetizers and Presidente beer as Henry spoke directly to the young third baseman who’d signed as a 16-year-old phenom and became one of the best hitters in the sport. For the first time, Henry offered Devers a $300-million contract.

“His eyes got as big as when he sees a fastball right in the middle,” said Cora. “And I was right next to him. I was like, ‘Chill, bro.'”

Devers turned it down.

The Red Sox had scheduled the flight and reserved the hotel in hopes of a quick resolution. They returned to Boston believing that a deal was not particularly close, but that negotiations had reached a definitive turning point. According to multiple people in the room and in the organization, the Red Sox came away from their face-to-face meeting believing that Devers wanted to make a deal, and that there was never going to be a better opportunity to make it happen. It was, in some sense, now or never.

Within three weeks, the Red Sox had the framework of the 10-year, $313.5-million extension that became official on Wednesday. It is the 10th largest contract in baseball history.

“We always felt he was a $300 million player,” Montes de Oca said. “And that was our goal. Once we got the OK to pass that $300-million barrier, that’s when we felt we had something.”


Xander Bogaerts and Rafael Devers are close friends, and Bogaerts’ massive deal with San Diego loomed over extension talks. (Winslow Townson/Getty Images)

The Red Sox first talked to Devers about a long-term deal in the spring of 2021. Those talks ultimately went nowhere and were tabled for the 2021 season. They resumed in the spring of 2022 when the Red Sox made an offer based on Matt Olson’s eight-year, $168-million extension with Atlanta.

It wasn’t enough to even start negotiations.

Olson had previously been used as a Devers arbitration comparison, so there was a certain logic to employing him as an extension frame of reference, but the Red Sox knew they’d eventually have to offer more. As it turned out, their opening offer was so far from what Devers was asking that the two sides didn’t even bother negotiating. Whatever back-and-forth occurred was more conversation than negotiation.

“Talking, but no movement at all,” Montes de Oca said of the early discussions.

Cora called Devers into the manager’s office at Yankee Stadium on Opening Day last season to make sure he wasn’t flustered by the offer and the lack of movement towards a deal.

“He’s like, ‘Alex, I’m making ($11.2 million). If I can’t live with that, what am I going to do?'” Cora said. “I had a pretty good idea when we had that conversation that at one point, before the start of 2023, we were going to get something done.”

Truth was, Devers didn’t want to become a free agent. He signed with the Red Sox as a teenager in 2013 and grew up with the organization. The club was filled with coaches and executives he’d come to think of as friends and mentors. He didn’t want to be short-changed, but he didn’t want to leave, either.

“This is an organization that has given me everything,” Devers said. “So that was a factor, but also, free agency isn’t easy. It’s a tough process. I just didn’t want to have to go through that.”

When the Red Sox failed to make the playoffs last season, assistant general manager Romero flew to the Dominican Republic to celebrate Devers’ 26th birthday on Oct. 24. Devers was hosting a party at his ranch, and Romero took a helicopter from the Santo Domingo airport to Devers’ compound, landing on his property near the pool. Dominican Academy manager Javier Hernandez and assistant director of Latin American operations Alberto Mejia were with him. Romero brought a birthday cake, and Devers showed off his prized peacocks, goats and chickens. No formal offers were discussed that day, Romero said, but Devers did ask pointed questions about the direction of the team and the club’s willingness to spend.

“We’d known Raffy’s No. 1 point, that he wanted to say here,” Romero said. “But (he) was also serious that he got a fair deal.”

The Red Sox made a new offer during the postseason. Braves third baseman Austin Riley signed a 10-year, $212 million deal in August, and the Red Sox offered a deal that was similar but bigger. It was still not at the $300-million threshold and was not nearly enough to reach an agreement, but it did start to shift the conversation towards a real negotiation. Ownership had given baseball operations some financial leeway to increase its offer as needed, and team president Kennedy estimated that the two sides made seven or eight counter proposals after the October offer.

When Henry agreed to present the first $300-million offer in person in December, it was Dominican Academy manager Hernandez and Dominican Academy coordinator Martin Rodriguez who tried to book a restaurant for the secretive meeting. It was imperative that they find a place as private as possible to avoid leaks or disruptions in the negotiations. Rodriguez found the hotel and secured the site. Once there, Henry delivered his message.

“That was a chance for John to speak directly to Raffy and speak directly to his representatives and encourage all of us to find a way home,” Kennedy said. “That was a big moment, probably the biggest moment in the negotiations.”

Montes de Oca was joined by REP 1 president Peter Greenberg, REP 1 CEO Chris Koras and REP 1 executive vice president Scott Nelson.

“My thought process was, (the Red Sox) wouldn’t come all the way to the Dominican Republic for no reason,” Devers said. “So, I had a lot of confidence that it was going to happen, and Nelson reassured me as well that the work was being put in.” … I’ve always had a sense that everyone here understands the amount of passion and work that I put towards the game. I felt that alone was enough to give me the confidence that something was going to get done.”

Cora said he flew to the meeting strictly “to be at that table when somebody tells another person that you’re going to make $300 million.”

The Red Sox thought the offer might be enough to seal the deal right then and there.

“We were hopeful that it would lead to a pretty quick resolution,” Bloom said. “It didn’t. There was a lot more back-and-forth that had to happen.”

Just days after the meeting, which remained secret for weeks, ESPN reported that the Red Sox and Devers were “galaxies apart” in their negotiations.

Internally, the Red Sox felt they were closer.

Devers did not accept their offer, but the conversation in Santo Domingo felt like a turning point for both sides. Neither was clinging to its best-case scenarios. Each was expressing a real desire to find a middle ground. Devers made it clear that he did not want negotiations to extend into spring training, and certainly not beyond Opening Day.

“He understood maybe he needed to compromise a little on his value,” Montes de Oca said. “But for him to compromise a little bit to be where he wanted to be, it was worth it.”

Believing they would never have a better opportunity to reach a deal, the Red Sox set themselves a soft deadline of the end of the year to get it done, with leeway into early January. Negotiations were put on hold for the Christmas holiday, but when they resumed the following week, the Red Sox approached them with a now-or-never sense of urgency.

“We kind of came together and said, ‘Look, if we’re going to do this, this is probably the week that it’s going to need to happen,'” Bloom said. “Everybody was engaged, and everybody was motivated, and I guess our social lives are such that we could all do something on New Year’s Eve.”


The Devers deal will do much towards defining Chaim Bloom’s tenure guiding Red Sox baseball operations. (Maddie Meyer/Getty Images)

On the morning of Dec. 31, the two sides met on Zoom. Devers’ agents were on the call along with Bloom, Kennedy and O’Halloran. Bloom and O’Halloran had also been in near-constant contact via slack, text and phone with two of the Red Sox’s front office money experts: chief financial officer Tim Zue and manager of major league operations Alex Gimenez. The Zoom meeting was not particularly fruitful – they still weren’t close to a resolution – but the conversation did lay out what Bloom later called the various “levers” that could be pushed and pulled to find common ground. Years and dollars were two of the levers, of course, but also the amount to be paid in a signing bonus, and the amount to be paid out as deferred money beyond the life of the contract. This was not a time for a bunch of voices. It was a time for a series of smaller conversations. Zue and Gimenez exchanged countless messages with each other, and then with Bloom and O’Halloran, working through the luxury tax ramifications, how the deferrals would affect the contract and other minute details that were necessary to have pegged down.

For the rest of the afternoon and well into the night on New Year’s Eve, Bloom and Montes de Oca talked many times one-on-one about the various issues that each side cared about most. They found that some levers could be tugged a little in one direction or the other.

“At some point that evening, before midnight, we got off the phone,” Bloom said, “and I felt like, ‘OK, I can see this coming together in a way that works for everybody.'”

Montes de Oca hung up feeling the same.

“My kids weren’t happy about me being on the phone until at least 11 pm, but it was for a good reason,” he said. “We love Raffy, and this is where he wanted to be.”

By New Year’s Day, each side could feel the momentum building towards a deal. They stopped haggling over the final details of an arbitration agreement and on Jan. 2 settled on a $17.5-million salary for the upcoming season. The extension wasn’t complete at that point, but the broad strokes of the final 10-year, $313.5-million deal were coming together. Bloom spent the rest of the week of Jan. 2 spearheading the final stages of negotiation. Later in the week, he messaged the Red Sox staff to say that the deal was done. An agreement was in place. Devers signed the largest contract in franchise history.

Romero, who 10 years earlier had helped lead the international effort to bring Devers into the organization, immediately sent Devers a text message using the “baby face” nickname that had followed Devers from the Dominican Republic to Boston.

“Carita,” Romero told him, “you’re rich!”

Devers had his extension, and the Red Sox had their franchise centerpiece.

“I think the strongest expression I can say once it’s done is relief,” Romero said. “You’re obviously excited for everyone involved, but relieved that we could get this out of the way now. We know we have a cornerstone player to build around.”

(Top photo: Billie Weiss/Boston Red Sox/Getty Images)

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