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SAN DIEGO — Jon Lester stood in a hotel ballroom in Boston last January and told a group of reporters he wanted nothing more then to sign a contract extension with the Red Sox and build on what had been a record-setting career. To the chagrin of his agents, Lester even said he was willing to give the team a discount to get a deal done.

“It should be easy,” Lester said that night, about 11 months ago. “I think everybody wants the same thing.”

A journey that started with smiles and quickly turned torturous ended late Tuesday night when Lester decided to sign with the Chicago Cubs for six years and $155 million.

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The Red Sox fell significantly short with an offer of $135 million.

Now Red Sox fans — and ownership — will have to endure the sight of former Sox general manager Theo Epstein grinning as Lester is introduced at Wrigley Field and professes his love for a new team.

Lester texted his new manager, Joe Maddon, with the news, which came after 1 a.m. on the East Coast.

“It’s not often you get to win the baseball lottery,” said Maddon, who took to the lobby of the hotel at baseball’s Winter Meetings to celebrate. “Jon Lester is a horse.”

Throughout the day, rumors flew about which team was the frontrunner with no clarity emerging. The Red Sox met with Lester’s agents, Seth and Sam Levinson, and made their latest appeal.

“I think we’ve been able to communicate as much as we need to at this point,” Sox general manager Ben Cherington said. “If there needs to be another conversation, we can certainly have another conversation.

“He’s going to have a lot of information in front of him and that’s his decision.”

The San Francisco Giants were the third team involved and willing to go to six years. But Lester eliminated the Giants first, calling GM Brian Sabean, manager Bruce Bochy, and catcher Buster Posey to thank them.

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With Lester off to Chicago, the Red Sox will turn to other options to find the two front-line starting pitchers badly needed to fill the holes atop their rotation.

The best free agent available is righthander Max Scherzer, who is almost sure to cost more than Lester and will be in no hurry to make a decision. Second-tier free agents include James Shields, Brandon McCarthy and Ervin Santana. None are at Lester’s level.

The trade market might be more promising. The Red Sox have a surplus of outfielders and a large parcel of prospects to deal. Cherington said Tuesday the Sox have offers out to free agents and trade proposals in the hands of other teams.

To bring back an ace like Cole Hamels (Phillies) or Johnny Cueto (Reds), the Sox would have to part with some of their best young players.

“At some point between the end of October and now, any starter that could conceivably be traded, we have talked to that team about,” Cherington said.

That could produce a deal before the Winter Meetings end on Thursday. But there are no artificial deadlines.

“We’re not there on a deal or anything like that. But we’ve had more conversations,” Cherington said. “We’re not a spread offense; we’re not moving down the field in big chunks. Three yards and a cloud of dust; we’re grinding away. Hopefully we get there soon enough.”

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Cherington said waiting on Lester hasn’t affected his ability to pursue other deals. The one holdup was learning whether the Sox would be adding a significant salary to keep Lester. Now that obstacle is gone.

“You can explore a lot of things and there are other things that you can still explore but not make as formal until you have some clarity on that,” Cherington said. “We’re not working in sequential order. We are aware of all the possibilities. We have to be sensitive to the bigger stuff because of the financial implications. But there’s all sorts of other stuff we’re working on.”

Tickets go on sale Saturday and fans will want quick answers. Losing Lester, a player they watched grow up and help win two World Series after beating cancer, will be painful. The Sox had every chance to keep him and missed them all.

The missteps began in March when they tried to take advantage of Lester’s loyalty with an opening offer of four years and $70 million, a figure well below his market value and now laughable considering what he ultimately received. Lester and his agents swiftly rejected the proposal and asked for negotiations to be tabled.

By July, the lack of communication between the sides led to the Sox trading Lester to the Oakland Athletics for outfielder Yoenis Cespedes.

“As we went through this past year and the attempts to sign Jon, it felt like at the trading deadline it was best for all involved to make that move,” manager John Farrell said on Monday.

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After squandering their chance to sign Lester in March, the Sox suddenly made a concerted effort after the season that included principal owner John Henry, who also owns the Globe, making at least two face-to-face appeals.

The Red Sox reminded Lester about his familiarity with the organization, his productive relationship with Farrell and the comfort his wife and two young sons had in Boston. But the trade at least partially severed those connections and made a reunion more difficult. Lester pitched well for Oakland and the once-foreign notion of pitching for another team took root.

Lester joins a long list of star players who left the Red Sox under convoluted circumstances.

There was All-Star catcher Carlton Fisk, who became a free agent when the team was a day late sending him a contract offer in 1980. He spent 13 years with the White Sox.

Bruce Hurst, a successful homegrown lefty, wanted to stay in Boston but received a lowball offer and fled for the Padres. He was 55-37 with a 3.22 ERA over the four seasons that followed.

Ace pitcher Roger Clemens departed in anger in 1996 with GM Dan Duquette saying the righthander was in “the twilight of his career.” Clemens went on to win 162 more games and four more Cy Young Awards.

Charismatic center fielder Johnny Damon, who said he would never sign with the Yankees, did just that in 2005 when the Red Sox failed to meet his price. Damon had four productive years in New York, helping the Yankees win the World Series in 2009.

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Lester leaves the Red Sox ninth in team history with 110 wins, fourth in strikeouts with 1,386 and seventh in pitching WAR at 30.7. Lester had a 2.11 ERA in 13 postseason games with the Sox — 0.43 in three World Series starts.

Related coverage:

■  Nick Cafardo | On baseball: Cubs manager Joe Maddon glad to land Lester

■  Jon Lester’s career highlights with Red Sox

■  Notebook: If Red Sox land Cole Hamels, it may be costly

■  Shaughnessy: On Jon Lester watch, stakes are high and information scarce

■  Red Sox make offer to pitcher Justin Masterson


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