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A 10-day trail led to Red Sox’ big makeover

Red Sox manager John Farrell woke up at 8:30 last Thursday morning and, as many of us do, rolled over to check his phone for messages. The first one was from general manager Ben Cherington.

Farrell knew enough not to be surprised. But the words were still jarring.

Call me when you can, we have something on Lester.

Farrell dialed quickly and learned that Cherington had traded ace lefthander Jon Lester and outfielder Jonny Gomes to the Oakland Athletics for outfielder Yoenis Cespedes and a draft pick.

Cherington had been awake for close to 35 consecutive hours, but for Farrell it was just the start of a day that would fundamentally change the team.


Over the next 11 hours, the Red Sox would make an extraordinary series of moves that amounted to one of the biggest upheavals in team history.

Lester and Gomes were the first of five prominent players traded.

“I went to bed knowing there were several teams that were possibilities,” Farrell said. “I woke up and Jon had been traded and Ben was giving me updates on other situations. I knew I had to get over there and join the fray.”

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Before the 4 p.m. deadline for trades, the Sox sent righthander John Lackey to the St. Louis Cardinals, lefthanded reliever Andrew Miller to the Baltimore Orioles, and shortstop Stephen Drew to the Yankees. The conference room within the baseball operations department at Fenway Park was the epicenter.

The Red Sox traded two starting pitchers with a combined 259 wins and four World Series rings to contending teams. They bolstered their fiercest rival and improved another division foe by sending them a reliever having the best season of his career.

Less than a year after winning the World Series, the Sox were sellers at the trade deadline. Cherington, Farrell, and others in the front office readily acknowledged their culpability for the team falling into last place and requiring such a radical makeover.


“We’re in this position because of the performance of the team, and the performance of the team is ultimately my responsibility,” Cherington said.

“If we had done a better job as an organization this year and performed better, then it’s not just likely but obvious that most of this stuff would not have happened today.”

Principal Red Sox owner John Henry, who also owns the Globe, refused to comment, as did team president Larry Lucchino, despite several requests. Team chairman Tom Werner spoke only in general terms, saying he was pleased with the ultimate result.

Henry, Werner, and Lucchino were active participants in the process leading up to the trades. Michael Gordon, an untitled limited partner whose stake in the team and Fenway Sports Group is more than all of the partners outside of Henry, was a visitor to the conference room as well.

The trades came in a flurry Thursday, one roughly every two hours starting with the Lester deal. But they were the result of 10 intense days of preparation, scouting, and decision-making.

“Coffee. A lot of coffee,” assistant general manager Mike Hazen said. “We put in a lot of late nights trying to figure this out.”

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Cherington was prepared to add players for a run at a playoff spot on the evening of July 21 when the Sox defeated the Toronto Blue Jays, 14-1. The victory was the team’s fifth in a row and improved its record to 47-52. In a season in which every team in the American League East appeared vulnerable, the Sox felt they still had a chance.


Five losses in a row changed that thinking. No one game flipped the switch from the team’s being a buyer to being a seller, it was more a collective realization that only one course of action made sense. They started making calls.

“No matter how we think the team should be playing or could play over the last 60 games or so, the math was against us,’’ Cherington said. “And if we’re really serious about building another team and trying to become as good as we can as quickly as we can, well, what do we need to find out the rest of the way to do that?”

Watch: Ben Cherington on Jon Lester contract talks

The Red Sox had their scouts change their focus and evaluate prospects the team could receive in return for established players. Professional scouting director Jared Porter made the assignments and information was gathered.

The Sox called their scouts to Boston late that week and held a meeting to discuss options. Cherington and his top assistants then took up residence in the conference room, contacting other teams to discuss proposals.

The room was crowded at times. Hazen and fellow assistant GM Brian O’Halloran were with Cherington for nearly every minute. Three executives who are often on the road — Porter; vice president of player personnel Allard Baird; and director of player personnel Dave Finley — returned to Fenway.


Former Sox catcher Jason Varitek, now a special assistant to Cherington, had a prominent voice, as did senior advisor Bill James and statistical analyst Tom Tippett.

As players were considered, screens flashed video of recent performances and relevant statistics as detailed scouting reports came up on laptops.

Lunch and dinner were brought in each day. The highlight, Cherington said, was a barbecue dinner from Sweet Cheeks, a neighborhood restaurant.

“I was taken aback at how prepared everybody was,” said chief operating officer Sam Kennedy, who spent time observing the process. “It was a collaborative effort with conversation and push-back.”

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The Red Sox communicated with all but three of the 29 other teams to discuss deals. For each of the four trades that were made that day, dozens were considered and rejected.

“Long days and long nights,” said Cherington, who was encouraged by the owners to be bold in his decision-making. “We knew coming into the week that we had a job to do.”

Some of the time proved wasted. Many teams offered the Red Sox package deals of minor league prospects, and those players were evaluated and debated at length. The Red Sox came close to dealing Lester to the Orioles on Wednesday for prospects, but waited. Another attractive offer came from the Miami Marlins.


In the end, the only prospect obtained Thursday was 21-year-old lefthander Eduardo Rodriguez from Baltimore, in exchange for Miller.

The Red Sox were more interested in major league talent, with the goal of the team’s getting back in contention next season. That made the process more difficult.

“We were sellers, but not in a conventional sense,” Farrell said.

The Sox delayed making any decisions until the early-morning hours of Thursday, believing the return for their players would only improve as the deadline drew closer.

The trade sending Lester to Oakland was agreed to at shortly after 3 a.m. Thursday. Medical reports had to be exchanged before the deal could be finished and Cherington suggested to his assistants that they bust out of Fenway and get breakfast at the 24-hour South Street Diner.

“We never did,” he said.

Hazen went to his home in Westwood instead, snatching a few hours of sleep before he returned to Fenway at 9 a.m., just after Major League Baseball approved the trade.

In California, Cespedes was sleeping when he received an unexpected call.

“It caught me by surprise,” he said Friday after arriving at Fenway. “Only God knows why things happen.”

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In this case, Athletics GM Billy Beane was the almighty. He wanted Lester badly enough to part with Cespedes, who made the All-Star team this season and was Oakland’s most exciting player.

Beane started seeking Lester a week before the deadline. But it was not until he broached the idea of giving up Cespedes that the Red Sox were drawn in. Adding Gomes, who had played for Oakland in 2012 and was popular in the team’s clubhouse, made the deal work for Beane.

“It’s a zero-sum game, and in Jon Lester, you’re dealing with someone who is one of the best at his position in the game and has been for a long time,” Beane said.

Cherington and Farrell contacted Lester to give him the hard news. Cherington had known the pitcher since 2002, his senior year of high school. When Lester came to Fenway to clean out his locker, Cherington made sure to be in the clubhouse.

“That was a thank you, an appreciation for everything he’s done, and good luck,” the GM said.

Lester, after learning he had been traded, went ahead with plans for a birthday party for his son, 4-year-old Hudson. He and his wife, Farrah, had invited friends and teammates to their home in Newton and were not going to disappoint the little boy.

Dustin Pedroia was there with his wife and children. He had not been expecting to hug his teammate goodbye.

“It’s a party for Jon’s son, and Jon had been traded,” Pedroia said. “This guy was our best pitcher. You know anything can happen but I thought we’d figure out a way to keep him.”

As the Lesters went ahead with their party, Lackey was traded to the Cardinals for outfielder-first baseman Allen Craig and righthander Joe Kelly.

Two hours later, Miller was sent to Baltimore. The tall lefthander, who rents an apartment with his family a block away from Fenway on Boylston Street, walked over to get the news in person.

“I’m excited that Baltimore wanted me,” said Miller, who emerged with a black Red Sox equipment bag slung over his shoulder. “But I’m sorry to be leaving.”

Of all the players, he seemed the least affected by the trade, having been dealt twice before in his career.

“It’s just part of the game and out of my control,” he said before waiting at the crosswalk to return home.

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The Red Sox did not have a game Thursday. Bench coach Torey Lovullo was in Maine to see his son Nick, an infielder at Holy Cross, play for the Sanford Mainers.

“Every time I looked at my phone it seemed like we traded somebody,” Lovullo said.

First baseman Mike Napoli stayed in bed until close to 11 a.m. He woke up only because Pedroia kept sending him text messages.

“Pedey finally got me and he was like, ‘You won’t believe all of this,’ ” Napoli said. “Our team was like a family after last year and now it was being broken up.”

Lester went to Fenway after his son’s party and encountered Henry. The two briefly hugged. Lackey arrived shortly after and left without speaking to any of the executives.

Gomes met with Cherington and Farrell. Before he left, Gomes went out to the field with a paper cup and filled it with dirt as a souvenir. Gomes also left behind a gift in the clubhouse, a white Red Sox jersey draped over Napoli’s chair.

It was signed, “No. 5 to Nap: Brothers and champs for life. Jonny Gomes.”

Gomes then climbed behind the wheel of a large red pickup truck and pulled out of the parking lot. Lackey had driven away without stopping to speak to the television cameramen holding vigil. But Gomes, ever agreeable, stopped for a brief interview.

“My phone blew up and I knew something had happened. The first person I talked to was Ben,” he said. “Rumors are rumors, you know? I don’t pay attention to rumors. This wasn’t my first rodeo with trade deadlines.”

After answering a few more questions, Gomes waved to some fans standing on the sidewalk and headed home to pack.

As the crowd dispersed, a man in a motorized wheelchair rolled down Van Ness Street past Fenway.

“All these trades,” he said. “It’s another Boston Massacre.”

But the Red Sox were not done. Inside the conference room, Cherington picked up his iPhone and saw a message from Yankees general manager Brian Cashman.

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The Red Sox and Yankees had not made a trade since 1997. But Cashman took note of the Red Sox dealing Lester, Gomes, Lackey, and Miller, and took his shot. He wanted Drew, with the idea of moving him to second base.

“I threw an idea Boston’s way when they started moving and shaking as much as they were,” Cashman said. “Once they declared themselves the way they did, I floated a text Ben Cherington’s way and we worked really quickly off of that.”

Cashman wanted Drew in exchange for utility infielder Kelly Johnson. Any concerns about helping the Yankees were swiftly brushed aside after the owners gave their approval.

“Given the circumstances, look, we hope it helps them. The Yankee thing really wasn’t an issue in that particular conversation,” said Cherington.

With the deadline drawing closer, there was little time to ponder the historical ramifications anyway. The Red Sox wanted to deal Drew so that rookie Xander Bogaerts could move back to shortstop. If Drew helped the Yankees win, so be it.

If anybody had pause, it was Cashman.

“There’s a great deal of respect between the Red Sox and Yankees, both of our sides,” he said. “It’s an amazing rivalry, but we’re certainly very careful when we do business with each other.”

As the trades were approved, home clubhouse manager Tom McLaughlin was on the phone with the new players helping them choose their numbers.

Cespedes was easy. He wore No. 52 in Oakland and that was available. Craig had No. 21 in St. Louis but that has not been given out in Boston since Roger Clemens left the team in 1996.

Craig was offered a few choices and asked for a minute to think about it. He called McLaughlin back and took the No. 5 made available when Gomes was traded.

Kelly, who wore No. 58 in St. Louis, took No. 56. Johnson took No. 7, which Drew had worn. When Yankees clubhouse manager Rob Cucuzza called Drew, he took No. 33, which had belonged to Johnson.

As the choices were made, McLaughlin called Majestic Athletic in Easton, Pa., and placed orders. Majestic supplies uniforms to every team and keeps a database with the jersey and pants sizes for every player based on measurements done during spring training. New sets of uniforms were shipped immediately.

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At the same time, McLaughlin and his staff were busy packing up any leftover belongings of those players who had been traded and readying the lockers for the newcomers.

“The uniforms were here the next morning, and thankfully everything was right. That might have been the busiest day I’ve had in 29 years on this job,” McLaughlin said.

That trade of Drew was made official about 15 minutes before the deadline. There was nothing else for the Red Sox to consider at that point. The phones finally stopped ringing.

Media analysts declared the Red Sox as one of the “winners” at the trade deadline. But those in the room were unanimous in saying there was no joy at making any of the moves, especially dealing Lester.

“Sobering,” Werner said.

It was more a sense of duty, an obligation to put sentiment aside.

“You put your blinders on and do what you feel is right for the organization at the time and moving forward,” Hazen said. “You can’t think of the personal side of it. It’s not fun; it’s a responsibility. Hopefully we did the right thing.”

More coverage:

Cafardo: Time will tell if Lester trade is a success

Jon Lester bids farewell to Red Sox Nation in Globe ad

Analysis: World of opportunity now awaits for Red Sox

Cafardo: Revamping offense was Red Sox’ priority

Red Sox manager John Farrell arrived at Fenway Park after a multitude of trades last week.Barry Chin/Globe staff

Pete Abraham can be reached at pabraham@globe.com. Follow him on Twitter @peteabe.