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FORT MYERS, Fla. — In hoping for an extension of a contract that will expire after the 2014 season, Jon Lester has said he would be willing to give the Boston Red Sox a hometown discount because he loves playing in Boston and has an aversion to change.

“I can deal with three or four new teammates, but not a whole new squad of them,” Lester, the southpaw ace, said Monday at the Red Sox’s training base.

Change of many varieties is an unavoidable part of the team-sports equation. Even after the bearded wonders of Boston rolled to the franchise’s third World Series victory in a decade, the center fielder and leadoff hitter Jacoby Ellsbury signed as a free agent with the hated New York Yankees. The power-hitting catcher Jarrod Saltalamacchia went to Miami. Shortstop Stephen Drew is without a contract, and Boston’s mandatory reporting date for position players is Wednesday.

Sunday brought a stranger kind of departure for the reconvening Red Sox when pitcher Ryan Dempster announced he would forgo the 2014 season and his $13.2 million salary. The resulting headline was of the man-bites-dog variety, an athlete leaving extraordinary money on the table because, as Dempster explained, he wasn’t physically up to playing and wanted to spend more time with his family.

“Obviously, people are going to say, ‘How can you walk away from that much money?’” Lester said. “But when he told me what he was doing, I said, ‘Congratulations.’ He’s been doing this for 20 years, and how many jobs are there where you can retire at 37 and not have to worry for the rest of your life?”

With a career 132-133 won-lost record, Dempster had already earned almost $90 million across 16 major league seasons, just one with the Red Sox. He still choked up when, as he finished speaking to reporters, several attending teammates applauded. But soon after the emotions came the analytics, leading to the big-picture consensus that the Red Sox were suddenly in better position to defend their title.

“It’s part of the business that when one of your guys leaves you’ve got to fill the hole,” Dustin Pedroia said. “You can do it from within or go outside the organization. We’re trying to do it from within, and everyone knows we have a pretty darn good farm system.”

Lester called Dempster “one of the best teammates I’ve had,” and other players said he was a significant contributor to the Sox’s much-celebrated 2013 chemistry. His most memorable on-field moment was a glaringly deliberate 92 mph fastball on a 3-0 pitch that crashed into Alex Rodriguez’s left elbow in an August game against the Yankees at Fenway Park, soon after Rodriguez returned to the lineup while appealing his drugs-related suspension.

Coming into camp, Dempster was slated to be the sixth starter in a five-man rotation. Every staff is fragile, but the coldhearted truth of the matter is that the Red Sox have several young arms — Brandon Workman, Allen Webster and Drake Britton, among others — who are eager to develop at the major league level. And now they have Dempster’s money to add to the $5 million they were saving for a potential midseason acquisition.

They could yet use the money to reach out to Drew, who has been seeking a multiyear contract. But 21-year-old Xander Bogaerts, who had a .412 on-base percentage in 12 postseason games at third base in 2013, said in an interview, “I’ve been told to take grounders at shortstop, no third base.”

It’s obvious that Ben Cherington, the Sox’s executive vice president and general manager, wants Bogaerts to be the everyday shortstop.

He hopes center fielder Jackie Bradley Jr. will put his 2013 struggles behind him and eventually cause people to cite the Yankees’ seven-year, $153 million contract for the 30-year Ellsbury — whose legs are crucial to his value — as an example of desperation begetting excess.

The more judiciously run organizations know when to cut ties, make room for young talent within a more self-assured veteran core. There is, of course, risk. The process of succession can go awry, or be delayed.

“The greatest teacher is between the lines,” said John Farrell, the Red Sox’s manager. “The question that’s always asked is, ‘Can these young players come up and help us?’ But it’s not just their physical ability. We know they have that. It’s what happens when they struggle.”