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Poll: Should Red Sox have upped offer to sign Jon Lester?

12.10.14 at 9:12 am ET
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Jon Lester decided to accept a reported six-year, $155 million deal with the Cubs late Tuesday night. The Red Sox apparently did not offer near that much money.

How do you feel about the Red Sox refusing to match the Cubs’ offer?

Should the Red Sox have upped their offer to sign Jon Lester?

  • No, a six-year, $155 million deal for a 31-year-old pitcher is not smart business (69%)
  • Yes, they have the money and they should have spent it (31%)
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Source: Cubs, Jon Lester agree to 6-year, $155 million deal

12.10.14 at 1:36 am ET
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Jon Lester's Red Sox career is now in the rearview mirror. (Jim Rogash/Getty Images)

Jon Lester‘s Red Sox career now is in the rearview mirror. (Jim Rogash/Getty Images)

SAN DIEGO — Almost a year after his proclaimed interest in returning to the Red Sox on a hometown discount, left-hander Jon Lester rejected his former team’s free agent overtures and instead chose to make his baseball home in Chicago with the Cubs, according to an industry source.

Lester agreed to a six-year, $155 million deal, the largest average annual value ($25.83 million) ever given to a pitcher on a multi-year deal in free agency. His deal with the Cubs includes a vesting option for a seventh year. The Sox’ final offer, according to another industry source, was for a six-year, $135 million deal with no seventh-year vesting option.

Lester’s decision followed a weeks-long process of visits with interested teams and two full days at the Major League Baseball winter meetings in which much of the industry’s activity seemed to depend upon his decision.

“You just wait for the white smoke,” Cubs manager Joe Maddon joked on Tuesday afternoon of the wait for Lester’s choice between his team, the Red Sox, Giants and Dodgers. “This is a guy when the game is really big he was always at his best. To possibly get this opportunity to work with him for the first time is very exciting. … [You] can’t have any more respect for a baseball player than we do for him now. For us to be able to pull this off it would be pretty outstanding.”

In choosing to sign with the Cubs, Lester joins a front office with whom he has a great deal of familiarity. Cubs president of baseball operations Theo Epstein, general manager Jed Hoyer and assistant GM Jason McLeod all have close relationships with the pitcher after spending years with him in the Red Sox system.

A case can be made that the fact Lester chose that group rather than a Sox organization with whom he spent the first 12 years of his career represented a particularly painful dagger for Boston. Lester was the first player drafted under the current Sox owners in 2002 and contributed to two World Series titles, foremost with a dominant performance for the ages in the 2013 postseason.

Lester had made no secret of his desire to return to the Red Sox, stating in no uncertain terms prior to the 2014 season that he would take less than full market value in hopes of remaining with the Sox for his entire career. But when the Sox made an initial four-year, $70 million offer to Lester in spring training, the pitcher and club saw insufficient common ground to continue talks during the season, and Lester didn’t re-open the door to in-season negotiations.

Still, even after the team traded Lester (and Jonny Gomes) to the A’s at the trade deadline for Yoenis Cespedes, the Sox remained adamant that they’d make a run at the pitcher when he arrived at free agency after the season following a 16-11 season in which he had a career-best 2.46 ERA and 220 strikeouts in 219 2/3 innings. That is precisely what they did, with team ownership meeting with him in the Atlanta area in November and principal owner John Henry traveling back to meet with the pitcher one-on-one again last week. The team showed a willingness to go to six years — the longest guarantee ever made under the Henry ownership group.

But ultimately, Lester, 30, opted to be a part of Chicago’s effort to end its 106-year championship drought. The Red Sox, who have two holes in their rotation, must now focus their attentions elsewhere as they pursue a top-of-the-rotation option for 2015 and beyond.

Read More: 2014 winter meetings, cubs, Jon Lester,

Dodgers, Giants informed they are out of Jon Lester sweepstakes

12.09.14 at 9:56 pm ET
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SAN DIEGO — The field is narrowing.

According to a major league source, both the Giants and Dodgers have been informed by Jon Lester that he is no longer being considered as possible landing spots.

Giants assistant general manager Bobby Evans — who told reporters earlier Tuesday that his team was “in the backseat” when it came to the services of Jon Lester — informed the media Tuesday night that Lester had informed San Francisco that it was no longer being considered an option by the free agent pitcher.

Later in the evening, the LA Times reported that the Dodgers were also no longer being considered by Lester.

It is believed that Lester is making a decision between the Red Sox and Cubs.

Check back for more …

Joe Maddon on Jon Lester sweepstakes: ‘Just wait for the white smoke’

12.09.14 at 7:26 pm ET
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SAN DIEGO — Cubs manager Joe Maddon said that he doesn’t know where free agent Jon Lester might end up or when he might make his decision. But the new Chicago skipper, whose club is one of the finalists for the left-hander’s services, said that he soon expects an indication of Lester’s intentions.

“I’m sure it’s not going to be much longer, I don’t think that it would be, but I have no information or knowledge about that. You talk about it, you just wait for the white smoke,” said Maddon. “I hope we win it. My role has been to ‘€‘’€‘ I spoke to him on the phone once. I’ve never spoken to Jon before that, adversarially with the Rays and the Red Sox for many years, always admired his work from a distance. This is a guy when the game is really big he was always at his best. To possibly get this opportunity to work with him for the first time is very exciting. So I honest to God don’t know where this is at right now. I did talk to him before ‘€‘’€‘ I think it was before Thanksgiving, actually. We had a great conversation, again, because I’d never really spoke with him before. It would be a great boon to us to have this come off.

“Can’t have any more respect for a baseball player than we do for him now,” added Maddon, who managed against Lester with the Rays over the last nine seasons. “For us to be able to pull this off it would be pretty outstanding.”

Read More: 2014 winter meetings, Joe Maddon, Jon Lester,

Manager Ryne Sandberg: Phillies would require ‘wow’ factor in return for Cole Hamels

12.09.14 at 6:54 pm ET
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Left-hander Cole Hamels had a 2.46 ERA for the Phillies in 2014 -- the same mark as Jon Lester had for the Red Sox and A's. (Brian Garfinkel/Getty Images)

Left-hander Cole Hamels had a 2.46 ERA for the Phillies in 2014 — the same mark as Jon Lester had for the Red Sox and A’s. (Brian Garfinkel/Getty Images)

SAN DIEGO — Need a top-of-the-rotation left-hander? Beyond Jon Lester, the obvious premium option on the market is Cole Hamels.

The Lester and Hamels markets unquestionably are interrelated. Any of the teams — Red Sox, Cubs, Dodgers, Giants — that are currently engaged on Lester represent obvious potential trade destinations for Hamels if they lose out on him.

As such, according to a source familiar with the Phillies’ thinking, Philadelphia will wait for a full exploration of the Hamels trade market until after Lester signs. At that point, a prospect bidding war could proceed quickly for the 30-year-old, who will represent a $24 million a year average annual salary as calculated for luxury tax purposes over the remaining four years of his contract, with an option for 2018 at $20 million (with an $8 million buyout).

Phillies manager Ryne Sandberg said that his team would require an enormous haul in order to deal Hamels, who was 9-9 with a career-best 2.46 ERA in 204 2/3 innings in 2014.

“I know with any of these players that [GM Ruben Amaro] wants a deal that’s going to be good for the Philadelphia Phillies going forward. Anyway that he can help the process and add players that can help us not only this next year but in the future, that’s the goal,” said Sandberg. “There’s no way that Ruben’s going to just give away a player.  I mean, we’d have to be wowed to give up a guy like Cole Hamels, which would be a wow that would help us with the process and go in the direction that we want to go. … I’m just waiting to see through this process to see what comes about. Whether Ruben gets wowed or not is yet to be seen. If not, then he’s on our pitching staff, and we build some more starting pitching depth around him.”

Though Hamels has the right to veto trades to 20 teams (reportedly including the Red Sox), the left-hander has told the team that he’d be open to leaving the Phillies. Read the rest of this entry »

Read More: 2014 winter meetings, Cole Hamels,

Source: Still not at stage for Jon Lester to receive final offers; Red Sox meet with agents

12.09.14 at 5:35 pm ET
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SAN DIEGO — According to a major league source, as of Tuesday evening, Jon Lester‘s representatives were not at the point where they were prepared to offer their client a presentation of final offers from the four teams involved.

The source goes on to clarify that Lester’s agents, Sam and Seth Levinson of ACES, met with the Red Sox earlier Tuesday. With the involvement of ownership groups from all teams slowing the process, there was still a strong possibility no decision would be made the pitcher until Wednesday.

In the mix for Lester’s services with the Red Sox are the Dodgers, Giants, and Cubs.

Giants assistant GM Bobby Evans on Jon Lester pursuit: SF ‘probably in the back seat of this deal right now’

12.09.14 at 4:18 pm ET
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Giants assistant GM Bobby Evans suggested some skepticism about his team's chances of landing free agent pitcher Jon Lester. (Jim Rogash/Getty Images)

Giants assistant GM Bobby Evans suggested some skepticism about his team’s chances of landing free agent pitcher Jon Lester. (Jim Rogash/Getty Images)

SAN DIEGO — While some have viewed the Giants as an emerging favorite in the sweepstakes for free agent left-hander Jon Lester, assistant GM Bobby Evans said on Tuesday that while his club remained engaged with the 30-year-old, he believed that his club is “probably in the back seat of this deal right now,” with Lester seemingly drawn to his significant pre-existing relationships with the Red Sox and Cubs.

“I think that ultimately Jon has a tough decision to make,” said Evans. “You have a player who’s very passionate about his teammates in Boston, he’s very passionate about the relationships he has with maybe two clubs, including the Cubs, so therefore I think it makes it a harder decision. We at some level may be in the back seat right now. That’s understandable because there are some good options for him.”

Evans said that the Giants delegation that met with Lester in the Atlanta area wanted to convey their high regard for the pitcher, the appeal of pitching in their run-suppressing home environment and the opportunity to work with a highly regarded catcher in Buster Posey, who has been part of three championship teams. Still, Evans said that the Giants are mindful that they can’t match Lester’s history with the Red Sox or the members of the Cubs front office.

“I think there are some things that are attractive about our situation, but I think heartstrings can play a role there,” said Evans. “I know that he’s a passionate guy and I think he’s got some strong and deep relationships with really two clubs at this point in Chicago and in Boston. We put our best foot forward and hope there’s an opportunity to draw him to us because we think he’s a game-changer.

“[But] I feel we’re probably in the back seat of this deal right now. I feel like there are some other guys driving this, and probably we’re staying in it but I’m not sure how strongly we’re a consideration considering the other options.”

Evans said that he “wouldn’t expect” a decision from Lester on Tuesday.

“No timeline,” he said. “We want it sooner than later but we understand he’s got a decision to make and it’s not an easy one.”

Source: A’s were ‘locked in’ on deal with White Sox for Jeff Samardzija

12.09.14 at 2:31 pm ET
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SAN DIEGO — According to an industry source, the Red Sox did not appear to be meaningfully in the mix in trade discussions with the A’s to acquire Jeff Samardzija. Instead, according to the source, the A’s appeared “pretty locked in” on the players whom they acquired from the White Sox — infielder Marcus Semien, right-hander Chris Bassitt, catcher Josh Phegley and Double-A corner infielder Rangel Ravelo — rather than trying to spawn a bidding war.

In some ways, that would appear to echo the approach that Oakland took to trading Josh Donaldson to the Blue Jays in exchange for infielder Brett Lawrie, right-hander Kendall Graveman, left-hander Sean Nolin and shortstop Franklin Barreto. The A’s consummated that deal without shopping Donaldson to other interested teams; some members of the Red Sox front office, for example, had no inclination that the third baseman was going to be moved and were caught off guard by the deal.

(For what it’s worth: Had the A’s made Donaldson available to the Red Sox, given their need for a third baseman and shortstop, the conversation likely would have started with Xander Bogaerts and grown from there. Whether it would have been in the Sox’ best interests to answer the team’s need for a third baseman while opening a hole at shortstop in a market that is lacking in legitimate everyday options at that position — instead of signing Sandoval (not Donaldson’s equal, but an above-average third baseman) and keeping Bogaerts is a fair and fascinating question.)

While that approach has yielded deals that have been subject to criticism in terms of a perceived light return, some in the industry point to Oakland’s successful track record — including three straight trips to the postseason — in suggesting that the A’s typically have a fairly precise handle on their needs and should be given the benefit of the doubt.

Read More: 2014 winter meetings, Jeff Samardzija, Josh Donaldson,

Sources: Red Sox make 1-year offer to free agent Justin Masterson

12.09.14 at 10:51 am ET
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The Red Sox have made a one-year offer to right-hander Justin Masterson. (Brian Garfinkel/Getty Images)

The Red Sox have made a one-year offer to right-hander Justin Masterson. (Brian Garfinkel/Getty Images)

According to industry sources, the Red Sox are one of multiple teams that have made a one-year offer to free agent right-hander Justin Masterson.

Masterson endured a season-long struggle with health in 2014 that stemmed from torn cartilage in his rib cage and a consequent buildup of scar tissue. The discomfort he felt as a result of that injury resulted in mechanical alterations and injuries, including discomfort in his knee and an impingement in his right shoulder that eventually required a cortisone shot in September. However, the diagnosis of scar tissue towards the end of the year offered something of a unified theory for the right-hander’s health woes, which contributed to a year-long struggle (7-9, 5.88 ERA in 28 games and 25 starts) with the Indians and Cardinals.  He is expected to be healthy for next season.

Given that he suffered a down year in 2014 (a season in which he turned down a three-year, $51 million extension offer from the Indians), Masterson appears to be in search of a one-year deal that would permit him to rebuild his value prior to the 2015-16 offseason — whether for talks about an extension with the club with whom he signs for next year or as a free agent. Because he’s a groundball pitcher, Masterson is less concerned about the home ballpark of the team with whom he signs than is typical of other free agents who sign one-year deals, and his relationship with the Red Sox front office (he was in the team’s minor league system under current GM Ben Cherington and current assistant GM Mike Hazen) and manager John Farrell (the pitching coach with whom Masterson worked upon arriving in the big leagues) represents a draw for him as he wades through his free agent options.

Read the rest of this entry »

Read More: 2014 winter meetings, justin masterson,

Source: Jon Lester’s decision could be pushed to Wednesday

12.09.14 at 3:36 am ET
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SAN DIEGO — According to a major league source, Jon Lester‘s decision as to which team he will sign with may drag on into Wednesday.

It was originally believed that the time it would take for Lester to pick a team wouldn’t stretch beyond Tuesday. But, because of the involvement of ownership for multiple interested teams, the process has been slowed.

The source suggests that there is still the possibility that an agreement is in place Tuesday, although it would likely be later in the day.

As of Tuesday morning, the Red Sox were very much in the mix for Lester’s services, with the Cubs, Giants and Dodgers also making strong plays for the free agent pitcher.

Monday, Red Sox manager John Farrell expressed optimism regarding the return of his ace pitcher, telling the assembled media at the winter meetings, “I think we’€™re still confident that we can sign Jon. He’€™s obviously still going through this free agency process. As we came into this offseason, there were a couple spots in the rotation that we needed to add to and address. We’€™re in the midst of that right now. We’€™re still optimistic that he’€™ll be in a Red Sox uniform. There’€™s a lot of history between the Red Sox and Jon. We obviously have a strong desire to bring him back, and yet hopefully this is coming to a little bit of a head here.”

Multiple sources continue to suggest that Lester likely won’t take the highest offer if he deems another team to be a better fit.

For more Red Sox news, visit weei.com/redsox.

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