Jon Lester may return to Boston after all

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Jon Lester may return to Boston after all

Jon Lester of the Boston Red Sox during photo day at City of Palms Park on February 26, 2006 in Ft. Myers, Florida. 

Photo Credit: Robert Sargent, Getty Images

Jon Lester #31 of the Boston Red Sox delivers a pitch in the first inning against the Oakland A's on September 26, 2007 at Fenway Park in Boston, Massachusetts.

Photo Credit: Elsa, Getty Images

The Boston Red Sox celebrated after sweeping the Colorado Rockies in four games to win the 2007 World Series in four games. The Boston Red Sox beat the Colorado Rockies 4-3 at Coors Field Sunday October 28, 2007. 

Photo Credit: Karl Gehring, The Denver Post/Getty Images

Starting pitcher Jon Lester of the Boston Red Sox celebrates with the trophy in the locker room after winning Game Four by a score of 4-3 to win the 2007 Major League Baseball World Series in a four game sweep of the Colorado Rockies at Coors Field on October 28, 2007 in Denver, Colorado.

Photo Credit: Jed Jacobsohn, Getty Images

Pitcher Jon Lester #31 of the Boston Red Sox watches his team from the dugout against the Tampa Bay Rays during the game at Tropicana Field July 1, 2008 in St. Petersburg, Florida. 

Photo Credit: J. Meric, Getty Images

Jon Lester #31 of the Boston Red Sox reacts after throwing a no hitter against the Kansas City Royals at Fenway Park on May 19, 2008 in Boston, Massachusetts.

Photo Credit: Jim Rogash, Getty Images

Jon Lester #31 of the Boston Red Sox deals to the New York Yankees on July 3, 2008 at Yankee Stadium in the Bronx borough of New York City.

Photo Credit: Jim McIsaac, Getty Images

Pitcher Jon Lester #31 of the Boston Red Sox delivers a pitch during a game against the Oakland A's on May 25, 2008 at McAfee Coliseum in Oakland, California. Oakland won 6-3. 

Photo Credit: Greg Trott, Getty Images

Jon Lester #31of the Boston Red Sox throws against the Tampa Bay Rays at Fenway Park, April 8, 2009, in Boston, Massachusetts. 

Photo Credit: Jim Rogash, Getty Images

Jon Lester #31 of the Boston Red Sox pitches against the Oakland Athletics at Fenway Park on July 30, 2009 in Boston, Massachusetts The Red Sox defeated the Athletics 8 to 5. 

Photo Credit: Rob Tringali, Sportschrome/Getty Images

Jon Lester #31 of the Boston Red Sox poses during photo day at the Boston Red Sox Spring Training practice facility on February 28, 2010 in Ft. Myers, Florida.

Photo Credit: Gregory Shamus, Getty Images

Jon Lester #31 of the Boston Red Sox lays on the mound after being hit in the knee by the New York Yankees Melky Cabrera #53 line drive during the game on September 25, 2009 at Yankee Stadium in the Bronx borough of New York City.

Photo Credit: Jared Wickerham, Getty Images

Jon Lester #31 of the Boston Red Sox wears a special edition hat in honor of Memorial Day as the Red Sox take on the Kansas City Royals on May 30, 2010 at Fenway Park in Boston, Massachusetts. 

Photo Credit: Elsa, Getty Images

Jon Lester #31 of the Boston Red Sox prepares to throw during the game against the Kansas City Royals at Kauffman Stadium on August 21, 2011 in Kansas City, Missouri.

Photo Credit: Ed Zurga, Getty Images

Boston Red Sox starting pitcher Jon Lester delivers against the Chicago White Sox during the first inning of a baseball game at Fenway Park in Boston Monday, May 30, 2011.

Photo Credit: Winslow Townson, AP Photo

John Lackey #41 and Jon Lester #31 of the Boston Red Sox congratulate teammate Kelly Schoppach #10 following their win against the Detroit Tigers during the game on July 30, 2012 at Fenway Park in Boston, Massachusetts. 

Photo Credit: Jared Wickerham, Getty Images

Starting Red Sox pitcher Jon Lester, pitches during a game between the Boston Red Sox and the Kansas City Royals at Fenway Park in Boston.

Photo Credit: Aram Boghosian, The Boston Globe/Getty Images

Boston Red Sox starting pitcher Jon Lester delivers to the Tampa Bay Rays in the first inning of an exhibition spring training baseball game in Fort Myers, Fla., Sunday, March 17, 2013. 

Photo Credit: Elise Amendola, AP Photo

Jon Lester #31 of the Boston Red Sox reacts after giving up two run against the Cleveland Indians in the 3rd inning at Fenway Park on May 25, 2013 in Boston, Massachusetts.

Photo Credit: Jim Rogash, Getty Images

Boston Red Sox starting pitcher Jon Lester delivers against the Baltimore Orioles during the first inning of a baseball game on Sunday, June 16, 2013, in Baltimore. 

Photo Credit: Nick Wass, AP Photo

Jon Lester #31 of the Boston Red Sox hugs Jarrod Saltalamacchia #39 after the Red Sox defeated the Detroit Tigers 20-4 on September 4, 2013 at Fenway Park in Boston Massachusetts. 

Photo Credit: Michael Ivins, Boston Red Sox/Getty Images

This multiple exposure image shows Boston Red Sox starting pitcher Jon Lester throwing during the seventh inning of Game 1 of baseball's World Series against the St. Louis Cardinals Wednesday, Oct. 23, 2013, in Boston.

Photo Credit: David J. Phillip, AP Photo

Boston Red Sox starting pitcher Jon Lester throws in the outfield before Game 1 of baseball's World Series against the St. Louis Cardinals Wednesday, Oct. 23, 2013, in Boston.

Photo Credit: Matt Slocum, AP Photo

Boston Red Sox relief pitcher Koji Uehara jumps into David Ross's arms after defeating the St. Louis Cardinals in Game 6 of baseball's World Series Wednesday, Oct. 30, 2013, in Boston. The Red Sox won 6-1 to win the series. 

Photo Credit: Matt Slocum, AP Photo

Jon Lester #31 of the Boston Red Sox celebrates with his son Hudson and wife Farrah Stone Johnson after defeating the St. Louis Cardinals 6-1 in Game Six of the 2013 World Series at Fenway Park on October 30, 2013 in Boston, Massachusetts.

Photo Credit: Jamie Squire, Getty Images

Jon Lester #31 of the Boston Red Sox reacts after walking a man in the sixth inning against the Kansas City Royals at Fenway Park on July 20, 2014 in Boston, Massachusetts.

Photo Credit: Jim Rogash, Getty Images

Jon Lester #31 of the Boston Red Sox looks in to the catcher before he delivers a pitch against the New York Yankees during the fifth inning in a MLB baseball game at Yankee Stadium on June 28, 2014 in the Bronx borough of New York City.

Photo Credit: Rich Schultz, Getty Images

Jon Lester #31 of the Boston Red Sox throws in the first inning against the Kansas City Royals at Fenway Park on July 20, 2014 in Boston, Massachusetts.

Photo Credit: Jim Rogash, Getty Images

Jon Lester #31 of the Oakland Athletics pitches in the in the first inning against the Kansas City Royals during the American League Wild Card game at Kauffman Stadium on September 30, 2014 in Kansas City, Missouri.

Photo Credit: Ed Zurga, Getty Images

Jon Lester #31 of the Oakland Athletics pitches against the Los Angeles Angels of Anaheim at O.co Coliseum on September 24, 2014 in Oakland, California.

Photo Credit: Ezra Shaw, Getty Images

Oakland Athletics starting pitcher Jon Lester looks into the seats after the third inning of a baseball game against the Chicago White Sox, Tuesday, Sept. 9, 2014, in Chicago.

Photo Credit: Charles Rex Arbogast, AP Photo

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When the Red Sox traded Jon Lester over the summer, conventional wisdom was that the lefty's days in Boston were done. After all, the team was unable to sign him to a long-term deal while holding exclusive negotiating power. The two sides were reportedly not even close on their proposals. So now that 29 other teams can bid for Lester's services, logic would seem to dictate that any chance of an extended stay in New England was all but over.

Not so fast.

According to ESPN Boston's Gordon Edes, a "well-connected baseball executive who has had conversations on the subject with the Red Sox" predicts Boston will eventually land the ace. But it will likely take several years and a lot of money. That executive believes it could be for six years and at least $120 million. That's a far cry from the four years and $70 million the organization offered him during the season.

A contract of that size contradicts the very philosophy the team adopted after the albatrosses that were Carl Crawford, Adrian Gonzalez, and Josh Beckett. OwnerJohn Henry has publicly expressed his concerns with long-term deals for players over 30, especially pitchers. And in an interview with BusinessWeek in April, he said, "Virtually all of the underpaid players are under 30 and virtually all the overpaid players are over 30. Yet teams continue to extravagantly overpay for players above the age of 30."

While it's been the general public understanding that the Red Sox will avoid such deals under all circumstances, GM Ben Cherington has opened the door to the possibility this week, telling reporters, "It's never been a hard policy. We've made exceptions, and I'm sure there will be another exception. It's a case-by-case thing. If all the boxes are checked, sure, there will be a longer term deal. It's just as we've done in the past."

That sounds like an executive setting the stage for a potential big move. And if the Red Sox are going to make one, Lester would be the logical choice.

The fact that he is a known commodity within the Boston front office is important. Not only does the team know he can pitch in Boston, but management is more familiar with his health than they would be for any other free agent. Lester has been extremely durable, throwing more than 190 innings in each of the last seven years.

But, he's only gotten better. He is coming off the best season of his career, and finished fourth in the Cy Young Award voting. The Red Sox could use a pitcher like that. Boston's starting staff allowed more runs than all but three teams in baseball last season. Cherington traded away nearly the entire rotation, and while there are many potential front-line starters making their way through the Boston system, they aren't ready to take on the role of the number one that the Sox need.

There's even the chance the Red Sox won't have to be the highest bidder for his services to get him back. Shortly after being traded to Oakland, Lester told reporters, "'I don't need to be blown out of the water. Why would I need to be blown out of the water? That doesn't make or break your decision, at least for me. I'm not going to the highest bidder. I'm going to the place that makes me and my family happy. If that's Boston, it's Boston."

And it might be Boston. WEEI's Rob Bradford reports the Red Sox are one of six teams showing legitimate interest in Lester's services. Cherington has already met with his agents, saying, "I met with them kind of socially and talked about all sorts of things. I expect the conversation will continue. They have to go through their thing. I still feel like the relationships are in place we can have those conversations." And, the pitcher and his agents will even meet directly with Boston ownership within a matter of days, another sign the team may be plenty serious in its interest of him.

All things considered, it makes little sense for the Red Sox to not be aggressive in trying to re-sign Lester. The general philosophy of not signing aging players to long-term, big money deals makes sense, lest you become the Yankees. But, there doesn't need to be a hard and fast rule against such signings, which Cherington has started to hint at this week. And, if there is going to be one player for whom to make such an exception this offseason, it should probably be Jon Lester.


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