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An inside look at how the Red Sox landed Chris Sale

Jonathan Daniel/Getty Images

At baseball’s general managers meetings in Scottsdale, Ariz., the second week of November, the Red Sox discussed trading for Tyler Thornburg with the Brewers and Chris Sale with the White Sox.

But there was no smoke indicating the possibility of a deal at a time when prices remained high. As Sox president of baseball operations Dave Dombrowski prepared to leave those meetings, however, some embers became visible. By Tuesday, they were on fire, leading to a franchise-altering day.

In talks with the White Sox, Dombrowski made a point of leaving the door ajar. Past requests by Chicago for major leaguers in return for Sale wouldn’t work, but if Chicago changed course and would consider a package of prospects, it should call.


On the way out of the meetings, Milwaukee GM David Stearns touched base with Dombrowski.

“[Stearns] said, ‘Dave, I know you asked me about Thornburg. We have interest in Travis Shaw. Maybe there could be a foundation, but it wouldn’t be one for one,’ ” recalled Dombrowski. “I said, ‘Well, it would be something we’d be interested in talking about.’ ”

The subsequent three weeks featured relatively little contact as teams awaited a new collective bargaining agreement.

The new CBA was settled on Nov. 30, four days before teams descended upon the Winter Meetings in Oxon Hill, Md., with a new sense for the rules that would guide their roster construction. However, Dombrowski wasn’t rushing to the phones.

Chris Sale is 1-1 in three career starts at Fenway Park.Charles Krupa/AP

“I think that’s usually not a good way to do things,” he said. “It’s not like signing a free agent. You need to have a pulse of what’s going on but not be jumping right away.”

On Dec. 2, Stearns suggested he and the Red Sox could work on building a three-player package around Shaw and middle infielder Mauricio Dubon.


At about 6 p.m., as Dombrowski was getting home from a day in his office at Fenway, he received a call from White Sox GM Rick Hahn, who made clear his intentions: Sale likely would be dealt during the Winter Meetings, and Hahn was contemplating different scenarios than in the past.

Whereas the White Sox had asked the Red Sox for big league talent when the sides talked after the 2015 season and during the 2016 season — according to multiple major league sources, in past talks the White Sox wanted young big leaguers from the Red Sox’ All-Star core — Hahn said Chicago would discuss a different package this time with Boston.

“[But] he emphasized it would have to be someone like [Yoan] Moncada in the deal,” Dombrowski said.

Just 19 months earlier, the Red Sox had signed Moncada as a 19-year-old amateur to a record-setting $31.5 million bonus, and Dombrowski believed in his potential to emerge as a star.

But he also recognized the likely cost of acquiring Sale, who’d been in the top six of AL Cy Young voting for five straight years, and was available on one of the most attractive contracts in baseball.

Listen: Dombrowski on the value and trade cost of Chris Sale


Red Sox senior VP of baseball operations Frank Wren received an intriguing phone call at his Atlanta home.

“[Dombrowski] said, ‘I just want you to know, it looks like things may be changing a little bit.’ Threw out a couple scenarios. ‘What do you think?’ ” recalled Wren. “He said, ‘Well, we’re going to have a lot to talk about when we have everyone gathered in D.C.’ ”


Dombrowski’s wife and son were out of their Brookline home in the afternoon, leaving him time to digest the new CBA. That day, Hahn reached back out to Dombrowski to discuss building a deal around Moncada and Michael Kopech, the rocket-armed righthander.

“I said, ‘Well, again, it’s a lot. I’m not saying we would do it, but it’s something that would be worth discussing,’ ” said Dombrowski.


The Red Sox front office arrived at the Winter Meetings still undecided on how to address the setup role. The team had an offer on the table to Koji Uehara, a move that could at least buy time while waiting to see if Joe Kelly or Carson Smith might develop into a reliable eighth-inning presence.

Dombrowski and Hahn had planned to touch base in the evening. To prepare for that conversation, Dombrowski asked VP of baseball research and development Zack Scott to prepare a study comparing Sale’s value with Moncada’s and Kopech’s.

“We did some analytical work on Sunday night for Monday, that if you look at the value of players, Chris Sale’s three years was not going to add up to [the value of having Moncada and Kopech under team contractual control for six big league seasons each],” said Dombrowski.

The conclusion wasn’t black and white — it was a close call based on the team’s internal evaluations of the prospects, close enough that it shouldn’t deter conversation..


Dombrowski hadn’t heard from Hahn when he went to sleep around 11 p.m. Around 11:30, however, he awoke to a text. The first snow of the winter in Chicago delayed the arrival of Hahn and the White Sox. The teams would touch base Monday.


The White Sox indicated early on that Yoan Moncada would need to be a piece in the trade package.Thearon W. Henderson/Getty Images

Red Sox officials trickled into Dombrowski’s suite early in the morning in advance of more organized conversation starting at 9 a.m. Roughly three dozen team officials crowded into the narrow suite on the 19th floor of the Gaylord National Resort and Conference Center, a classroom-like setup with all chairs facing a wide desk where Dombrowski sat in the front.

The conversation was largely philosophical: What did it mean to pursue deals that would make the team better over the next three years but that would have consequences beyond that? That question was examined on and off throughout the day while negotiations took place with the Brewers (largely haggling around the third piece in the deal for Thornburg) and White Sox (examining the potential third and fourth pieces in a deal).

Dombrowski felt conflicted, helping to explain why he held off discussing the possible Sale deal with ownership.

“I really gave a lot of hard thought on making the type of deal,” said Dombrowski. “The young players we were giving up weren’t just, ‘Forget about it.’ I really gave it a lot of thought before I kind of came to conclusions in my thought processes.”


Dombrowski started to engage principal owner John Henry, who also owns the Globe, and chairman Tom Werner by phone Monday afternoon after he’d decided that he wanted to pursue a deal. Team president Sam Kennedy also was in the loop, with all parties wrestling with giving up potential future franchise cornerstones in Kopech and especially Moncada.

Listen: Dombrowski on the Red Sox’ decision-making process

“You listen to [Henry and Werner] and respect them. They can overrule me on whatever they want,” said Dombrowski. “They said, ‘You know what? It’s your decision.’ I think if we decided not to do it from a baseball perspective, they’d be fine. And when we decided to do it, they were thrilled.”

According to several major league sources, in the afternoon the Red Sox told the White Sox it might not work out. The White Sox wanted 20-year-old third baseman Rafael Devers as the third prospect.

If the Red Sox were dealing another young third base option in Moncada, they weren’t about to part ways with a player who has drawn comparisons with a lefthanded version of a young Adrian Beltre.

“We kind of separated not knowing what would happen on Monday afternoon, not knowing if they were going to make a deal with someone else,” said Dombrowski, who declined to discuss any players who did not end up in the final deal. “Rick was open. He said, ‘I’ve got one team that’s offering us four players. I’ve got one that’s offering us five players. But we like your players and would take these three.’ I said, ‘We really don’t feel good about that situation.’ ”

A lull occurred, during which the Red Sox focused on their deal with the Brewers. As the Thornburg deal advanced, reports suggested the Nationals — anchoring a package with righthander Lucas Giolito and outfielder Victor Robles — were the favorites to land Sale.

The Red Sox weren’t sure where things stood that evening, but given that no reports had surfaced that any team was including an established young big leaguer, Dombrowski found it hard to believe that any of the rumored packages would knock Boston out of the mix as long as the Red Sox were offering Moncada and Kopech.

Michael Kopech now heads to Chicago after Boston drafted him in the first round in 2014.Stan Grossfeld/Globe Staff/Boston Globe

As night came, the Sox were barreling toward finishing the Thornburg deal. The Brewers wanted hard-throwing righthander Josh Pennington as the third piece alongside Shaw and Dubon. The Red Sox were open to that deal, but Dombrowski needed to call Hahn to make sure that none of those players would prevent a Sale deal.

“[Hahn] said, ‘If we get off of what we’re asking, [the Brewers package] wouldn’t hold it up,’ ” Dombrowski said.

The Red Sox and Brewers could move ahead on the Thornburg deal – and with the Sox anticipating the addition of a pitcher who should make in the vicinity of $2 million as a first-time arbitration-eligible player in 2017, the team could also pursue a first baseman, knowing how much money they had to work with.

The team immediately engaged Moreland’s agent, Bob Garber, while waiting for the Thornburg deal to reach its conclusion and awaiting word from the White Sox.

Around 9 p.m., Dombrowski heard back from Hahn. The White Sox wanted to know if the Red Sox would be open to a deal with outfielder Luis Alexander Basabe and righthander Victor Diaz as the third and fourth pieces behind Moncada and Kopech. Dombrowski didn’t need to consult with his colleagues to offer an answer.

“I said, ‘Well, we do like [Basabe and Diaz], but we wouldn’t let them stand in our way,’ ’’ said Dombrowski. “I haven’t even gone into the other room, but I know our pulse.’’

Around 10:30 p.m., Dombrowski took a call about the Brewers deal.

“We all heard [Dombrowski] say, ‘Hi, David,’ to David Stearns while he was walking out. So we knew he was talking to Milwaukee,” recounted Wren. “He came back and said, ‘The medicals are clear [on Thornburg]. And I just talked to Rick Hahn and it’s done.’ . . . We were shocked.”

The room erupted.

Listen: Dombrowski on how the final trade package came to be

“There was a collective roar. There was applause, for sure. It really was a hell of a surprise. No one expected that to be the call,” said manager John Farrell. “He was in the room literally no more than five minutes. I don’t know how you get two phone calls in. He came out and said, ‘We’re done with this one, and we’ve got that one.’ ”

Dombrowski tried to temper the outlook a bit.

“I said, ‘No, no, no. It’s not done yet.’ There was exuberance but it wasn’t done yet,” said Dombrowski.

Dombrowski clarified that he’d followed the conversation with Stearns by placing a quick call to Hahn to see if the Red Sox front office should break for the night. Hahn informed Dombrowski that he liked the Red Sox’ four-player package and thought that there was the basis for a deal, but he wanted to take some time to perform final due diligence on Basabe and Diaz while also taking a last survey of opinion on the packages on the table from involved teams.

Hahn assured the Red Sox he wouldn’t make a deal without talking to them the next day. He told Dombrowski to expect a call at 10 a.m. Red Sox officials broke for the night around midnight, not knowing if there would be a deal for Sale but feeling good about their chances.

Hahn had his group break for rest at a similar time, but for a White Sox GM about to transform his franchise, slumber proved elusive.

“We probably broke for the night as a group close to midnight,” said Hahn. “I don’t think I slept that night, but that was more things going through my head as opposed to meetings.”


Rick Hahn kept open lines of communication with Dave Dombrowski.Cliff Owen/AP

Red Sox officials filtered back into the suite during the morning, just as the White Sox did in theirs.

“We were debating a couple packages at the time that morning,” said Hahn. “It was late in the morning that we ultimately decided that the Red Sox package was the one we were going to accept for Chris.”

Hahn called Dombrowski at 10 a.m. to tell his Red Sox counterpart that his room was ready to proceed but that he’d first have to talk with White Sox owner Jerry Reinsdorf. Reinsdorf was supposed to check in with Hahn at 11 a.m., but that got pushed back to 11:30.

At 11, the Red Sox and Brewers announced the Thornburg deal. Red Sox officials weren’t tipping their hand about Sale, but they were waiting anxiously for word from Chicago.

Finally, at 1:15 p.m., Hahn called back: The White Sox would agree to the deal, pending review of the medicals. At 3:30, that process played out, and the teams had an official deal. Again, the Red Sox’ suite erupted. This time, Dombrowski didn’t temper it.

“The real celebration is after the medicals are cleared,” said Dombrowski. “That was the big cheer, shake hands, fist bumps for some people, that type of thing. That’s the actual exuberance.”

At 3:45 p.m., the Sale deal was announced, with a news conference featuring Dombrowski and Farrell about a half-hour later. Around 6 p.m. word trickled out that the Red Sox had reached agreement with first baseman Mitch Moreland on a one-year, $5.5 million deal.

“When [Dombrowski] targets a guy, he gets him,” said Farrell. “He’s not really worried about what the perception is. He’s most concerned with acquiring players that are going to allow us to win the most right now.”

Alex Speier can be reached at Follow him on Twitter @alexspeier.