The Devers deal, behind the scenes

This story was excerpted from Ian Browne's Red Sox Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

Behind the scenes, the Red Sox -- and namely chief baseball officer Chaim Bloom -- had a unique way of ringing in 2023.

It was New Year’s Eve, typically a time for festive social gatherings, yet Bloom spent much of it holed up in his home office.

The mission? To close a deal with star third baseman Rafael Devers.

Unbeknownst to the general public, the Red Sox had built momentum toward a mega extension -- the largest contract in club history -- in the preceding weeks. But New Year’s Eve represented closing time for Bloom and Nelson Montes de Oca, who represents Devers.

“If there was a breakthrough, it was probably on New Year’s Eve,” said Bloom. “It took several conversations. Zooming with these guys, they’re great guys, but it’s not how I want to spend next New Year’s Eve. And then I had some phone conversations with Nelson, and that’s where we started to see that we might be able to get something done.”

It takes two to make a deal, and Bloom’s persistence was reciprocated by Montes de Oca and his agency -- REP 1 Sports.

“We spent a lot of hours on December 31,” said Montes de Oca. “My kids weren’t happy about me being on the phone until at least 11 p.m., but it was for a good reason. We love Raffy, and this is where he wanted to be. This is a place that he loves, and he deserves to be happy.”

The terms of an extension that starts in 2024 (10 years, $313.5 million, a source told MLB.com's Mark Feinsand) were agreed upon on Jan. 4, largely a result of those New Year’s Eve negotiations.

But the first big step came, in Red Sox chairman Tom Werner’s words, “around Dec. 14.”

That was when Red Sox owner John Henry, president/CEO Sam Kennedy, Bloom and assistant general manager Eddie Romero flew to Santo Domingo, Dominican Republic, to meet face to face with Devers.

This was one week after Xander Bogaerts had slipped away in free agency to the Padres, angering Red Sox Nation.

But with Boston’s ownership and front office well represented on that day in the Dominican Republic, they made it clear to Devers they had no interest in seeing him get to his walk year, let alone free agency.

Manager Alex Cora, knowing from his talks with the front office that Devers was about to get an offer in the range of $300 million, decided to join in on the meeting with Devers.

“I was talking to [my partner] Angelica, and I said to her, ‘I want to be there just to hear when somebody tells you that you're gonna make all this money.’ And his reaction was great,” said Cora. “It was priceless. His eyes got as big as when he sees a fastball right in the middle. And I was right next to him, I was like, ‘Chill, bro.’ But he was great. The conversations were great.

“The fact that John was there, I think it was very important for him. And I know with everything that was going on with the market, everybody thought like, ‘One more year go out there and see what you can get.’ But he was very genuine, very transparent. He wants to be part of this, he loves it. He loves playing at Fenway Park, he loves the city. The fact that the proximity to the Dominican too I think that that helps. And obviously having Dominican icons to lead this organization in the last 20 or 25 years, I think that that helped.”