Jon Lester Rumors

Extension Notes: Lester, Masterson, Wood

Extension season is unquestionably upon us, with several notable deals going down in recent days. What else might be forthcoming? Last year, between February 17th and April 4th, major league clubs committed a cool $641.4MM to extend nine players over a total of 45 years.

We just took a look at the latest on Chase Headley and the Padres, who seem at a standstill as the third baseman approaches his walk year. Yesterday, we heard that the Reds and Homer Bailey could be approaching a lengthy new deal. Here are some more notes on potential extension situations around the game:

  • The Red Sox have yet to initiate extension talks with Jon Lester, the lefty said today. As Peter Abraham of the Boston Globe reports, however, Lester remains unconcerned. The 30-year-old indicated that he was willing to talk through the season. "If it's something we do get done in Spring Training, great," said Lester. "If it's not, I think you have to take everything as it comes. If that involves going through the season still talking or getting it done early, you have to play it by ear." He also made clear that he stands by earlier statements that he hopes to reach a deal to stay in Boston, but did not promise a breezy negotiation. "I'm not going to go back on what I said," Lester explained. "I said what I said from the heart and I mean it. We'll see where it goes from there. We've still got a long way to go. It's going to be a tough process."
  • Justin Masterson and the Indians are making final preparations for their arbitration hearing on Thursday, reports Paul Hoynes of the Cleveland Plain Dealer. But Masterson — who will become a free agent in 2014 if he does not reach a new deal — indicated that he was still hoping to talk out of the adversarial process. Though apparently aimed at his 2014 salary, rather than long-term possibilities, Masterson's comments were interesting. "We're seeing if it's possible if we can make something happen before we leave [for the arbitration hearing]," said Masterson. "We're trying to see if we're being too stubborn or not. We're trying to be smart and reasonable. We're definitely moving a little bit here and there to see what can happen."
  • After posting a breakout year just in time for his first season of arbitration eligiblity, Cubs hurler Travis Wood says that he has had little dialogue about an extension, reports Mark Gonzales of the Chicago Tribune (subscription link). After landing a $3.9MM contract to avoid arbitration, it does not sound as if Wood is expecting further discussions before the start of the season. "We'll see what happens," said Wood. "I would love to stay here, but right now we've got to get focused on spring and get ready for the season." 

Bowden’s Latest: Free Agency, Scherzer, Drew, Lobaton

Jim Bowden of ESPN and MLB Network Radio spoke with multiple agents and executives over the weekend and got contradictory takes on the reasons for so many top free agents remaining unsigned (ESPN Insider required and recommended). Agents told Bowden that they (and the MLBPA) feel that the heightened media coverage resulting from social networking has damaged players' market values. Reports from media members about how teams value players and whether or not they've made offers to players could be violations of the CBA, those parties told Bowden. Meanwhile, executives said to Bowden that the market is simply full of players with baggage (draft pick compensation, PED usage, inconsistent performance) and added that agents entered the offseason with unnatural expectations for their clients.

Here are just some of the highlights from a jam-packed column from the former Nationals and Reds GM…

  • Max Scherzer and Jon Lester are the two most likely candidates from next year's crop of free agent starting pitchers to sign an extension, Bowden writes. Despite the fact that Scherzer is a Scott Boras client (Boras prefers his clients to test the open market), Scherzer seems to want to remain loyal to the Tigers. However, Bowden notes that an extension would still need to be somewhere close to Scherzer's market value, which Bowden pegs at a whopping $196MM over seven years.
  • The Red Sox have made a two-year offer to Stephen Drew, one source told Bowden. The value of that reported offer is unclear, as is the date on which it was made.
  • The Nationals have discussed Jose Lobaton trades with the Rays as they look to add a backup catcher for Wilson Ramos. Lobaton figures to be expendable for the Rays, as they project to have a strong defensive tandem of Ryan Hanigan and Jose Molina behind the dish. Shedding Lobaton's $950K salary would seem to be more beneficial to the tight-budgeted Rays than most teams, particularly if they don't have a roster spot for him.
  • The Dodgers are pushing for an infielder over another starting pitcher and hope to have a deal done within the next 48 hours. Los Angeles isn't likely to bid on any of the remaining free agent starters unless they're willing to take a short-term deal, as Dan Haren did to play near his hometown.
  • Kendrys Morales is the most likely free agent to be this year's version of Kyle Lohse, writes Bowden. He notes that the Orioles — who still have about $15MM to spend — and Mariners remain interested in the switch-hitting Scott Boras client. Both are still in on Nelson Cruz as well. MLBTR readers seem to agree with the Morales/Lohse comparison; in the poll I conducted earlier this morning asking which Top 50 free agent would be the next to sign, he drew the fewest votes.
  • The Royals and Indians are both highly unlikely to be able to lure back their respective free agent pitchers, Ervin Santana and Ubaldo Jimenez. The Blue Jays are a likely landing spot for both pitchers.

Quick Hits: Free Agents, Braves, Ortiz, Lester, Rays

The MLBPA has spoken to Major League Baseball COO Rob Manfred about their concerns over team executives talking about whether or not they're negotiating with free agents, which is a violation of the collective bargaining agreement, FOX Sports' Ken Rosenthal reports.  Some players are also upset at the slow pace of the free agent pitching market, and while Rosenthal says the union could consider filing a grievance, such an action would be hard to prove given that teams have already spent close to $2 billion on free agents this offseason.

Here's some more from around baseball on Super Bowl Sunday…

  • The Braves will have to make some tough decisions about which of their young core players they want to extend while keeping their payroll in check, Mark Bradley of the Atlanta Journal-Constitution writes (subscription required).  The experience of many of Atlanta's best young players is another issue, Baseball Prospectus' Ben Lindbergh tells Bradley, since "most of them have established themselves. (The Braves) possibly might have already missed the window of getting a good deal.” 
  • The Red Sox are wary about making too long a commitment to 38-year-old David Ortiz given how aging designated hitters can so quickly decline, Scott Lauber of the Boston Herald writes.  Ortiz is under contract through 2014 and recently said he would like another year added to his contract.  While Ortiz's age is a concern, Lauber notes that if the Red Sox don't extend Ortiz and he has another big season, the Sox will then be forced to sign him through at least 2016 to keep him in Boston.
  • Jon Lester is another Red Sox player mentioned in extension rumors, and John Tomase of the Boston Herald looks at the somewhat shaky history of left-handed starters who sign expensive contracts into their 30's.  Since Lester has said he would give the Red Sox a hometown discount, Tomase thinks a five-year, $100MM extension could work for both sides.
  • The Rays are still having talks about trading catcher Jose Lobaton, Marc Topkin of the Tampa Bay Times reports.  Lobaton looks like the odd man out behind Ryan Hanigan and Jose Molina, though Topkin notes that the team could still bring Lobaton to Spring Training in case one of their regulars gets injured.  If another team develops a catching need later in the spring, as well, the Rays can explore moving Lobaton then.
  • Also from Topkin's piece, the Rays have focused on adding depth this offseason to give themselves plenty of roster flexibility and options heading into Spring Training.
  • The Indians believe that Joe Smith was their biggest bullpen loss this winter, Terry Pluto of the Cleveland Plain Dealer writes, not former closer Chris Perez.  The Tribe rebuilt their bullpen and hope that John Axford can cinch the closing job, Vinnie Pestano returns to his old form and that young arms Bryan Shaw and Cody Allen continue to deliver quality relief innings.  Pluto notes that the Indians hope Shaw turns into a new Smith, and the club sees Allen as a future closer.
  • Baseball America's Matt Eddy recaps the week's minor league transactions.


Cafardo’s Latest: Arroyo, Cruz, Burnett, Middlebrooks

Nick Cafardo of the Boston Globe shares a few hot stove items in his latest Sunday column…

  • Bronson Arroyo has been looking for a three-year deal or at least a vesting option for a third year, which could be holding up his market.  If Arroyo was willing to settle for a flat two-year contract, Cafardo opines, he could find a deal, possibly with the Diamondbacks; Cafardo reported earlier this week that Arizona was "beginning to kick the tires" on the veteran right-hander.  Arroyo recently said that he has yet to receive a concrete offer from any team, despite a lot of interest from around the league.
  • The Dodgers are another team who "are very interested" in Arroyo but don't want to give him a guaranteed third year.
  • Nelson Cruz's market is beginning to heat up, and “there could be up to four or five teams who could take the plunge in the end," a Major League source tells Cafardo.  This interest could manifest itself into a multiyear deal for Cruz, though Cafardo notes that the slugger could still have to settle for a one-year contract.  We've recently seen the Mariners, Orioles, Rangers and Twins linked to Cruz in rumors, though Texas and Minnesota only seem interested at a greatly reduced price.
  • Cafardo thinks the A.J. Burnett sweepstakes is down to the Pirates, Phillies and Orioles, though he wouldn't be surprised if the Yankees were also exploring a reunion with the veteran right-hander.  The Rays and Blue Jays have also been connected to Burnett, though it seems more likely that Burnett will choose a team located closer to his home in Maryland.
  • The Marlins have "asked a lot" about Red Sox third baseman Will Middlebrooks but there doesn't seem to be a trade fit.  Miami is one of several teams who have asked Boston about Middlebrooks' availability, but the Sox don't want to give up on Middlebrooks' power potential.  Even if the Red Sox re-signed Stephen Drew to play shortstop and Xander Bogaerts took over at third, Middlebrooks would still receive playing time alternating between third and first base.
  • While Jon Lester recently said he would take a hometown discount to remain with the Red Sox, Cafardo points out that it might not be a huge discount, as Lester also noted that "you never want to be the guy that takes the market backward."
  • The Red Sox will experiment with Ryan Lavarnway as a first baseman during Spring Training, GM Ben Cherington confirmed.  Since Boston is so deep at catcher at both the Triple-A and Major League levels, Lavarnway's only chance at continued playing time may be as a Triple-A first baseman.
  • "There’s a feeling that a team like the Yankees may pluck Fernando Rodney, or someone of his ilk, to ensure they have another closer in case David Robertson breaks down or isn’t up to the task," Cafardo writes.  Rodney was reportedly drawing interest from four teams, though the Yankees hadn't spoken with him since November and may not have enough remaining payroll space to add to the bullpen.

Lester Would Take Discount To Stay In Boston

While the game's best lefty just signed a record-breaking extension, don't expect Clayton Kershaw's groundbreaking deal to impact extension talks between fellow southpaw Jon Lester and the Red Sox. Lester told reporters today, including Jason Mastrodonato of MassLive.com, that he knows he won't get free agent market value on an extension but still wants to remain in Boston:

"I understand that to stay here, you're not going to get a free-agent deal. You're not going to do it. You can't. It's not possible. You're bidding against one team. I understand you're going to take a discount to stay. Do I want to do that? Absolutely. But just like they want it to be fair for them, I want it to be fair for me and my family. If we can get to something hopefully in Spring Training, that's awesome."

Lester recalled the extension inked by Dustin Pedroia — an eight-year, $110MM deal (seven years, $100MM of new money) that was dwarfed by the 10-year, $240MM contract Robinson Cano signed with the Mariners this offseason: "That's what he wanted to do. I understand that. That's my choice, that's his choice." That agreement was reached in Spring Training. As ESPNBoston.com's Gordon Edes writes, Lester said he is hopeful that the he and the Red Sox can also work out a deal in the near future, but he wouldn't put any sort of deadline on extension talks. However, he added that he's yet to personally speak to GM Ben Cherington about an extension.

The 30-year-old Lester is currently set to earn $13MM this coming season after the Red Sox exercised a club option on him following the 2013 campaign. That option came at the tail-end of a five-year, $30MM contract extension Lester signed at age 25. Though he's headed for a significant pay increase even if he takes a hometown discount, Lester stated that the Red Sox are his No. 1 priority and added, "I want to be here 'til they rip this jersey off my back." Lester is represented by ACES, who negotiated Pedroia's extension last year.


East Notes: Braves, Price, Lester, Machado, Cishek

The Braves' front office has a busy day on its hands, notes David O'Brien of the Atlanta Journal-Constitution (on Twitter). Atlanta has seven arbitration eligible players they'll hope to take care of today: Craig Kimbrel, Jason Heyward, Freddie Freeman, Mike Minor, Kris Medlen, Chris Johnson and Jordan Schafer. He also tweets that a multi-year deal is unlikely to be reached with any of the seven. As MLBTR's Tim Dierkes tweeted earlier today, the Braves are one of several "file and trial" teams that either settle before exchanging figures or say they will head to a trial, which means GM Frank Wren and his staff will have their hands full today. Here's more out of baseball's Eastern divisions…

  • Rays ace David Price knows there's still a chance that he will be traded even after agreeing to a one-year, $14MM contract to avoid arbitration, writes Marc Topkin of the Tampa Bay Times. However, Price wants to remain with the Rays and says that the closer Spring Training gets, the more confident he is that he will stay. Price said that he can't imagine being traded once camp opens, and he thinks making it to February would be a good indicator that he won't be dealt: "Probably Feb. 1 would be a time period that I think would kind of let me know that I would be here."
  • Clayton Kershaw's record extension will impact future deals for starters, but its impact on Red Sox lefty Jon Lester is minimal, writes Scott Lauber of the Boston Herald. Lauber writes that there are no other players in Kershaw's stratosphere, noting that Lester compares more favorably to Cole Hamels. Boston will likely approach Lester about an extension during Spring Training, he adds.
  • The Orioles and Manny Machado received good news yesterday following Machado's visit with Dr. Neal ElAttrache, as one source told the Baltimore Sun's Dan Connolly that Machado is six to eight weeks ahead of schedule. That would place Machado ready to contribute on Opening Day, Connolly notes (Twitter links).
  • Signing closer Steve Cishek to a multi-year deal has not been considered as a serious option by the Marlins, MLB.com's Joe Frisaro reports in his latest Marlins Inbox piece.

AL East Notes: Carp, Lester, Arroyo, Jays, Rodriguez

Here's the latest from around the American League East:

  • Red Sox first baseman/outfielder Mike Carp could still be dealt before Opening Day, reports Jason Mastrodonato of MassLive.com. Though Boston has reportedly held out for a substantial return for Carp, and the club values the depth he provies, he might be worth more to other clubs who could deploy him more regularly.
  • Meanwhile, extension talks still have yet to begin between Jon Lester and the Boston front office, reports WEEI.com's Rob Bradford. Clayton Kershaw's extension does not necessarily serve as a comparable for Lester's purposes, says Bradford, but his absence from the open market could have an impact.
  • The Orioles are having ongoing discussions with free agent starter Bronson Arroyo, reports Jon Paul Morosi of FOX Sports (via Twitter). We learned recently that Baltimore had active interest in the veteran.
  • Confirming recent reports, Blue Jays GM Alex Anthopoulos said today that the price of pitchers on the free agent and trade market remains too high for the club's liking, Sportsnet.ca's Shi Davidi tweets.
  • Recent comments from Alex Rodriguez and Yankees owner Hal Steinbrenner indicate that both sides believe a return to the field in 2015 is a realistic possibility. Rodriguez sounds as though he has accepted the likelihood that he will ultimately sit out the entire 2014 campaign, but a spokesman said Rodriguez would "get ready for 2015 should the judge rule against him" in his court challenge against his full-season suspension. Steinbrenner, meanwhile, said that Rodriguez is "an asset" on the field and insisted the club would take a business approach to dealing with Rodriguez's situation going forward.

Gammons On Top Starters, Shields, Blue Jays, Drew, Polanco

In two pieces today for GammonsDaily.com, Peter Gammons discusses a variety of hot stove topics. In particular, even before Clayton Kershaw's market-busting extension earlier today, Gammons noted that the price of starting pitching has been a hot topic among baseball GMs.

  • The two key situations driving market pricing, he writes, are the Masahiro Tanaka sweepstakes and how the Rays handle David Price. Tanaka could command $120MM or more from the Yankees or Dodgers, says Gammons. As for Price, Tampa is increasingly inclined to hold onto their ace at least until the trade deadline, when they can try to extract a higher price or hold onto him for a postseason run. 
  • These situations could have a substantial impact on several other high-end starters that are set to become free agents next year. James Shields has let the Royals know that he is looking to score a contract on the magnitude of Zach Greinke's six-year, $147MM deal.
  • Meanwhile, the Red Sox and Reds do not plan on approaching key extension candidates Jon Lester and Homer Bailey, respectively, until Spring Training.
  • After disappointing returns on some of their major pitching acquisitions last year, the Blue Jays are not going to engage in any bidding wars for starting pitching, Gammons says. The club will instead "build on youth and rehabs," and will only jump into the mix for arms like Ervin Santana or Ubaldo Jimenez if they "fall down to [Toronto]."
  • Agent Scott Boras has increasingly given indication that free agent Stephen Drew is willing to play positions other than shortstop, says Gammons, which may increase his appeal to both the Yankees and Red Sox. As Andy Martino of the New York Daily News writes in a separate piece, Boras says that Drew has suitors other than the Sox and Mets, though he declined to name them.
  • Already considered one of the game's top prospects, Pirates outfielder Gregory Polanco has raised his stock even further with big numbers (including a .428 OBP) in he Dominican winter league. Polanco, 22, could have an impact by the mid-season of 2014. More importantly for the Bucs' long-term plans, one National League GM tells Gammons that the prospective Pittsburgh outfield of Polanco, Andrew McCutchen, and Starling Marte "will be the best outfield in the game." 

Red Sox Notes: Lester, Drew, Tanaka

Jon Lester is entering his last season under contract with the Red Sox and Brian MacPherson of the Providence Journal explores what it might cost Boston to re-sign Lester to a new multiyear deal.  Lester will be 31 on Opening Day 2015, so MacPherson uses the age 31-34 years of Cole Hamels' contract as a model, adding a guaranteed fifth to propose a five-year, $100MM extension for Lester.  While Lester re-established his value in the postseason and the Sox have been willing to lock up homegrown players, MacPherson also wonders if the club is confident enough in its young pitching depth to let Lester go rather than pay him a big salary through that would be his decline years.

Here are some more Red Sox-related items, all from Peter Abraham of the Boston Globe

  • The Red Sox currently hold all the leverage on Stephen Drew, and that leverage could become "a hammer," Abraham writes.  Since Boston seems willing to wait out Drew's market, the relative lack of interest in the veteran infielder makes Abraham believe the Sox could offer Drew a one-year, "take it or leave it" type of offer if Drew is still unsigned by mid-January.  If Drew turns the offer down, the Sox will be content with collecting the compensatory draft pick when Drew signs elsewhere, and Boston's desire for those valuable picks could make them pass on Drew anyway, Abraham notes.
  • "There is no sign yet that the Red Sox are interested" in Masahiro Tanaka.  As Abraham notes, Boston's young pitching depth and recent trend away from big-money free agent deals would seem to hint against a move, and signing Tanaka could impact a possible Lester extension.
  • Abraham cites Jesse Crain as "an interesting name" for the Sox considering Crain's history with pitching coach Juan Nieves and new catcher A.J. Pierzynski.  The Cubs, Astros and Rockies are a few of the teams known to have an interest in Crain this offseason.  Abraham opines that the Red Sox need bullpen depth since he doesn't think Koji Uehara will be as durable following Uehara's career-high 73 games and 74 1/3 innings pitched in 2013.

AL East Links: Choo, Drew, Lester, Yankees

As we continue to round up leftovers from Day Two of the Winter Meetings with an eye toward Day Three, let's check in on the latest notes from around the AL East….

  • In a piece for ESPN.com, Jerry Crasnick breaks down all the teams that could make a run at Shin-Soo Choo, including the Red Sox, Orioles, and Yankees. Crasnick concludes that the lack of very strong candidates doesn't necessarily bode well for Choo's chances of landing a $130MM+ contract, but cautions, as always, not to underestimate Scott Boras.
  • if Stephen Drew is willing to sign for two years or less, he'll likely just return to Boston, tweets Newsday's David Lennon, who adds that the Mets will probably need the Red Sox out of the mix to have a real shot at the shortstop.
  • Scott Lauber of the Boston Herald explains why Cole Hamels' contract with the Phillies may provide a blueprint for any extension talks the Red Sox have with Jon Lester.
  • The Yankees' decision to sign three free agents who required draft pick compensation should help keep the team contend in the short term, but may further stunt the growth of the farm system, writes Brian Costa of the Wall Street Journal.