How the Red Sox’ trade frenzy came about

It was approximately 3:30 Thursday morning when Red Sox general manager Ben Cherington came to an agreement on a trade that would send ace lefthander Jon Lester and outfielder Jonny Gomes to the Oakland Athletics.

It was just the start of an unprecedented series of moves for the Red Sox, making for one of the most dizzying days in team history.

The last-place Red Sox tore apart the team that won the World Series last fall, trading Lester, Gomes, shortstop Stephen Drew, righthander John Lackey, and lefthanded reliever Andrew Miller to teams in playoff contention.


The return was significant. Oakland sent All-Star outfielder Yoenis Cespedes to the Sox. The St. Louis Cardinals traded outfielder Allen Craig and righthander Joe Kelly in return for Lackey.

Get Sports Headlines in your inbox:
The most recent sports headlines delivered to your inbox every morning.
Thank you for signing up! Sign up for more newsletters here

The Yankees, who had not made a trade with the Sox since 1997, dealt infielder Kelly Johnson for Drew, and the Baltimore Orioles received Miller in exchange for promising 21-year-old lefthander Eduardo Rodriguez.

The deal involving Drew came only 30 minutes before the 4 p.m. deadline for trades.

“I think everybody is stunned,” said Gomes as he drove away from Fenway Park in his red pickup truck.

RELATED | Shaughnessy: Just what are the Red Sox up to?


The 48-60 Red Sox, hopelessly out of contention a year after winning it all, have fully turned their attention to next season with 54 games to play.

“We had to find a way to take advantage of the unfortunate position we were in and try to kick-start a little bit building the next team,” said Cherington, who said he didn’t sleep for two days plotting all the moves.

Of the 25 players who were on the playoff roster last season, only 14 are still with the organization. Seven have been traded, four of them on Thursday.

Cespedes and Craig are expected to be in the lineup for Friday night’s game against the Yankees, and Kelly will join the rotation next week.

Rookie Xander Bogaerts is being moved back to shortstop and Will Middlebrooks is returning from the minors to play third. Those moves were what motivated the trade of Drew.


A team that on Wednesday had a strong rotation and a weak offense now has a pitching staff loaded with unproven talent but a much-improved offensive attack.

‘There’s nothing sort of celebratory about this.’

Cespedes is the centerpiece. The 28-year-old from Cuba is an athletic and exciting player with a flair for dramatic plays. He has 17 home runs this season, three more than the Red Sox had out of their entire set of outfielders.

“A really powerful, dynamic player in his prime who fits in our ballpark in the outfield. We’ll probably take a look at him in right field and see sort of how he looks out there,” Cherington said.

RELATED:Trade deadline day recap: Who’s here, who’s gone

Cespedes, who is signed through the 2015 season, was second in the American League Rookie of the Year voting in 2012 but has seen his batting average, on-base percentage, and slugging percentage drop since.

Still, his power potential made the deal work. Cespedes represented a better player than the Red Sox were likely to find in the free-agent market this winter.

“We’re excited to have him. He’s someone clearly we don’t have,” Cherington said. “That did become a priority for us to see if we could get a little bit of a jump start on adding to the offense at the deadline.”

Lester, 30, leaves the Red Sox at the top of his game, having gone 10-7 with a 2.52 earned run average in 21 starts. His 149 strikeouts are sixth in the American League and he is fifth in ERA.

Lester joins an Oakland team that is in first place in the American League West and has the best record in baseball. After helping lead the Red Sox to a World Series title, he has a chance to repeat that accomplishment with his new team. Lester gives Oakland a formidable rotation that includes Jeff Samardzija, Sonny Gray, and Scott Kazmir.

RELATED | Cafardo: Revamping offense was Red Sox’ priority

Lester was a favorite in the organization, a homegrown talent who beat lymphoma early in his career to help win two World Series. He was 110-63 over parts of nine seasons with the Red Sox. He is ninth in team history in wins, fourth in starts, and fourth in strikeouts with 1,386. Only Roger Clemens, Tim Wakefield, and Pedro Martinez had more.

“Tough decision with people who have meant a lot to the Red Sox who I’ve known for a long time and done great things for the organization. So you start thinking about that and that’s hard,” Cherington said.

Lester will be a free agent after the season and has said he would be agreeable to returning to Boston. One aspect of the trade that appealed to the Red Sox was the knowledge that the Athletics were unlikely to retain Lester and that he would become available.

Watch: Ben Cherington on Jon Lester contract talks

Ben Cherington says Jon Lester contract talks “just didn’t happen enough”

“He’s an Oakland A right now. I don’t think it’s right for me to talk about that other than to say, looking back, that we certainly had a desire to engage on a contract conversation with him and that conversation just didn’t happen enough for whatever reason,” Cherington said.

Gomes, a platoon outfielder, had a big impact on the 2013 World Series champion Red Sox but was hitting .234 with six home runs and 32 RBIs this season. He returns to Oakland, where he played in 2012.

“There’s a spot in my house forever for my Red Sox jersey. Scooped up some Red Sox dirt to take that home,” Gomes said. “That [World Series] ring, that ring’s a lifer. I was fortunate to have the opportunity to wear that uniform.”

The 30-year-old Craig has played primarily right field and first base on his career. He is having a down season, hitting .237 with seven homers and 44 RBI for the Cardinals. But Craig hit .312 with an .864 OPS and 46 home runs from 2011-13.

Cherington said that dealing Lackey along with Lester required getting a starter pitcher in return and Kelly fit the criteria. The Cardinals also received minor league lefthander Corey Littrell and $1.75 million.

Watch: Ben Cherington on Red Sox trades

Red Sox general manager Ben Cherington on today’s trades

Once that deal was finished, the Sox turned to trading Miller. His 2.34 ERA over 50 appearances and 14.7 strikeouts per nine innings had created a demand. He was on the team last year, but was injured and could not play in the postseason.

“We had more calls on Andrew Miller than any other player on our team. Every contender in baseball pretty much called us on Andrew Miller because he fits for everyone,” Cherington said.

Miller also will be a free agent after the season and said he “absolutely” would consider a return to Boston.

“It’s exciting. I get a chance to pitch for a team that could go to to the playoffs,” he said. “I didn’t want to leave here but if I have to go, I’m glad it’s to a team like that.”

RELATED:How other big Red Sox deadline deals worked out

The trade of Drew came last. It was essentially a salary dump as the Red Sox will save approximately $2.8 million. They sent the Yankees $500,000 and took on Johnson, a utility player on the disabled list.

Drew left the Red Sox as a free agent after the Series, went unsigned, and returned in May. He hit .176 in 39 games.

“In retrospect, that move didn’t work out the way we wanted it to. Now it’s an opportunity to move [Bogaerts] back and use the rest of the year to let him play and we’ll see where we are,” Cherington said.

In what has been a bad year for the Sox, Thursday may have been a day that changes the fortunes of the team. The Red Sox remade the roster after finishing in last place in 2012 and went on to win the Series. Now they’re starting over again.

“There’s nothing sort of celebratory about this. These moves are made because collectively as an organization we haven’t performed well enough,” Cherington said.

Related coverage:

Dan Shaughnessy: Just what are the Red Sox up to?

Nick Cafardo: Revamping offense was Red Sox’ priority

Trade deadline day recap: Who’s here, who’s gone

How other big Red Sox deadline deals worked out

Meet the new Red Sox

Jonny Gomes gave a thumbs up as he drove away from Fenway Park.
Barry Chin/Globe staff
Jonny Gomes gave a thumbs up as he drove away from Fenway Park.

Peter Abraham can be reached at Follow him on Twitter @PeteAbe.