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10 Degrees: The Red Sox’s best move is to trade Jon Lester

Jeff Passan
Yahoo Sports

Two years ago, amid the chaos of a season crumbling around them and the eventual fire sale that paved the way for a championship, the Boston Red Sox very quietly let teams know that Jon Lester was available.

He was in the midst of his worst season, coming off the beer-and-chicken mess of 2011, stifled by manager Bobby Valentine, and after initial discussions with the Atlanta Braves didn’t go far, the Red Sox found a more-than-willing trade partner: the Texas Rangers.

The talks went beyond tire kicking, multiple sources with knowledge of the negotiations told Yahoo Sports. Names were exchanged. Permutations went back and forth. And for the second time, the Red Sox were threatening to deal Lester to the Rangers. The first time, of course, was as the third piece of the 2003 trade that almost sent Manny Ramirez to Texas and Alex Rodriguez to Boston.

Eventually, the 2012 talks fizzled. Texas got bounced in the wild-card game. The Red Sox rode Lester’s rebound year into the 2013 postseason, where he posted a 1.56 ERA and won a pair of World Series games. And now Boston is faced with an altogether different choice, one of its own doing, frankly, because its owners’ hubris put general manager Ben Cherington in an awfully difficult position.

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Jon Lester has a 2.52 ERA this season. (AP Photo)

Jon Lester has a 2.52 ERA this season. (AP Photo)

Because for the third time, the Red Sox are entertaining the idea of trading Lester, now 30, now fully developed, now in the midst of the best season of his career. And the difficulty is that if the Red Sox hadn’t insulted him this spring with a ludicrously under-market contract offer in the first place and followed up throughout the season with paltry increases far from commensurate to his growing value, they wouldn’t have to worry about the wisdom in trading him now – and if it destroys any chance of him re-signing once he hits free agency this offseason.

Instead, that is exactly where the Red Sox stand. Every start brings Lester closer to the open market, earns him millions more from teams frothing for a big, strong, front-of-the-rotation sort with legitimate playoff bona fides. Similarly, the Red Sox understand that is the very sort of pitcher postseason contenders want, and with the Red Sox stuck in last place and selling like the Duke brothers offloading frozen concentrated orange juice, dealing ...

1. Jon Lester is not just a possibility; it should be an imperative. Because here is the truth one Red Sox insider admitted to Sunday: The likelihood of Boston re-signing Lester lessens by the day, and the team ought to salvage what it can now by fetching a prospect package instead of the late first-round draft pick it would get by tendering him a qualifying offer after the season.

The Red Sox understand Lester’s tack from the start was that he wanted a fair-market deal. A four-year, $70 million offer was not fair; it was Larry Lucchino’s attempt at larceny. Carlos Zambrano, a far lesser pitcher than Lester, got a five-year, $91.5 million deal in 2007, when MLB revenues were $5.5 billion. Today, they are pushing $9 billion. To even start a negotiation there reeked of bad faith and showed Boston’s motivation and disinclination to sign a pitcher who will spend the entirety of the deal in his 30s.

And that’s not an altogether bad organizational philosophy. In fact, it’s probably a pretty smart one. The problem is, the Red Sox have tried to have their cake and eat it, continuously following up with offers that don’t come close to reflecting the shift in Lester’s market. His 2.52 ERA ranks behind only Chris Sale, Felix Hernandez and Scott Kazmir in the American League, and among AL pitchers with more than a strikeout an inning, his 4.7-to-1 strikeout-to-walk ratio trails just David Price, Sale, Felix and Corey Kluber.

He is having the sort of season that will convince more than a few teams to start at Cole Hamels money (six years, $144 million) and move from there. His fastball velocity has shown no signs of abating. Lester has missed two starts in the last seven years – and they were because of a lat strain, not any arm problems. If a pitcher is going to get huge free-agent money, he needs the sort of pedigree Lester brings.

Boston is a smart enough organization that it understands this, and considering the grace with which Lester has carried himself throughout this, any attempts to paint him as greedy or otherwise would be foolish. This is nothing more than a case of a team overplaying its hand, and lucky enough for the Red Sox, they’re in a scenario where it’s somewhat salvageable thanks to ...

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With the Rays rolling, it doesn't make sense for them to move David Price. (AP Photo)

With the Rays rolling, it doesn't make sense for them to move David Price. (AP Photo)

2. David Price leading the Tampa Bay Rays back from the dead. With a nine-game winning streak, a rotation that’s suddenly frightening even without the injured Matt Moore and a softer-than-silk AL East, the Rays – the 7½-games-back Rays – are close enough to contending that trading Price no longer seems right.

The Red Sox making Lester available muddles the market for Price, too, though it’s fair to say they are two wildly different commodities. Lester is a rental; Price is an ace under control through 2015, which means there’s the added value of a first-round pick if he bolts via free agency next offseason. More than that, as good as Lester has been, Price is the superior pitcher, a 28-year-old who has been even better than in his Cy Young-winning 2012 season.

With Price, a resurgent Alex Cobb, super soph Chris Archer, rookie Jake Odorizzi (124 strikeouts in 106 2/3 innings) and the returning Jeremy Hellickson, the Rays have the best pitching in the AL East, and it’s not close. The question, per usual, is whether they can hit, and that remains a maybe. The Rays are far from buyers yet, and they’re not sellers, either. They’re in the sort of limbo ...

3. Troy Tulowitzki finds himself two days after the team that gave him $157.5 million forgot how to spell his last name and a day after he ended up at Yankee Stadium on the same day his team was playing a game.

Yes, Tulowitzki wanted to see his idol, Derek Jeter, one last time, and he was close enough in Philadelphia – where he’s got an appointment Monday to visit his hip doctor – to make that happen. That is all well and good. At the same time, Tulowitzki is smart enough to know that showing up at a Yankees game when he’d love for the Colorado Rockies to trade him to New York is inviting anger from the front office.

And maybe that’s not a bad thing. It’s a dysfunctional front office, a group with a general manager who spends much of his time on the farm system, an assistant general manager who runs the major league roster and an owner who’s far too meddlesome for his own good. Tulowitzki is a prime example of that.

The St. Louis Cardinals expressed significant interest in him last offseason. They continue to reach out to the Rockies, as have the New York Mets, who are prepared to offer top pitching prospect Noah Syndergaard in a deal for the 29-year-old. And the response is: Not yet. We’re not ready to deal him. We want to hear it from him.

Which is to say: We want him to be the bad guy, not us. It’s a ludicrous way to run a business, of course, and it highlights how little confidence the Rockies have in themselves to make the sort of a deal that reinvigorates and re-energizes a ball club in desperate need of both. Front-office dithering can set franchises back years, something the ...

4. Cliff Lee negotiations – or non-negotiations, as they are – are helping compound with the Philadelphia Phillies. Perhaps the most important quality a franchise can possess is self-awareness, and the utter lack of it in Philadelphia – the simple fact that management didn’t just see this cratering coming but do something about it – speaks to the situation it’s in currently.

Take Lee, whose chances of being traded before the July 31 deadline are next to nil – and whose contract makes a deal prior to the Aug. 31 waiver deadline deal similarly unlikely. Especially if Philadelphia continues to ask for a return of any kind, as two executives with interest in Lee said it continues to do.

Lee tests the axiom that there’s no such thing as a bad one-year deal. Because his contract calls for a $25 million salary next year and includes a 2016 option with a $12.5 million buyout, which would make Lee’s 2015 salary perhaps $37.5 million. And if he does throw 200 innings next year, that activates an option for $27.5 million in ’16, meaning a pitcher who missed two months with an elbow injury would be due $52.5 million for his ages 36 and 37 seasons.

This is what not knowing who you are or what you are does. This is how you end up with ...

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Ryan Howard makes a lot of money, and he simply isn't producing. (AP Photo)

Ryan Howard makes a lot of money, and he simply isn't producing. (AP Photo)

5. Ryan Howard for $25 million next year, $25 million the year after and a $10 million buyout in 2017, while in his age-34 season he sports a lower slugging percentage (.385) than Billy Hamilton, Dee Gordon and Denard Span.

Howard’s contract is the tenure of Phillies GM Ruben Amaro Jr. in a microcosm, a bloated, far-beyond-necessary albatross that’s taking a powerhouse franchise and plunging it into a dark, dank period. The Phillies are old and not getting young anytime soon. They’re bad and not getting good anytime soon. Their best asset is Marlon Byrd, who happens to be the best cheap bat available, and Amaro for some reason gifted him no-trade privileges to two teams that could use him, Seattle and Kansas City, according to CBS Sports.

Certainly it wouldn’t hurt a team in need of power like Kansas City to take a flier on Howard if the Phillies ate all the money and didn’t want anything of substance in return – if, essentially, they were paying him to go away – but they’re not there yet. It’s similar to ...

6. Matt Kemp and his tenuous future with the Dodgers. Kemp wants to be traded somewhere he can play center field – please, Pfizer, develop that self-awareness pill for far too many in baseball – and nobody is biting, not at the Dodgers’ price. One report suggested Kemp and Lester could be the centerpiece of a deal, which prompted an executive to say: “Kemp and Julio Urias maybe.”

Around $114.25 million remains on Kemp’s contract, which runs through 2019. He is OPSing .775, striking out in more than a quarter of his at-bats, barely running three seasons after threatening to go 40-40 and so hampered in the field that the Dodgers stuck Yasiel Puig and His Merry Band of Defensive Adventures in center field over Kemp.

Seattle continues to monitor Kemp, with a hoard of prospects available if the Dodgers warm to the idea of eating lots of money. In the meantime, he’s just a backup choice, a future DH in the Mariners’ minds, with Marlon Byrd and Drew Stubbs their leading possibilities, according to a source with knowledge of their plans.

The 2011 version of Kemp was a revelation, everything the Dodgers had hoped in his development. He was 27 years old, and another half-decade of such years would have put him on the sort of ...

7. Hall of Fame track that so many others in their mid-20s have flashed. Making it there takes the sort of longevity personified by Greg Maddux, Tom Glavine and Frank Thomas, three players widely believed to have played into their 40s without the help of performance-enhancing drugs.

As they have for the last seven years, as they will for as long as the Hall of Fame remains an entity, PEDs played a large role in the induction weekend. This time it was the Hall’s doing, shortening the number of years a player can remain on a ballot, which long-term makes sense – why let a player fester for 15 seasons when 10 is plenty appropriate – and short-term may well punish the PED users whom the Baseball Writers Association of America continues to keep out of the Hall.

Now, this could be a good thing. A number of writers have said they want more time to process the Steroid Era, to understand the mechanics of it before rendering a final decision on PED users, and this is the sort of ticking clock for them that didn’t exist before. It’s not just the alleged users, Barry Bonds and Roger Clemens. It’s those punished purely on speculation, like Mike Piazza and Jeff Bagwell.

Perhaps those taking a moral stance against PEDs and the Hall intermingling will recognize that they already do, with the serious amphetamine usage that pervaded post-World War II baseball, and moreover that to deny PED users is to change history. The Hall exists to reward the best players. A Hall without the aforementioned four fails, and many more to come, fails to do so.

By staying silent on PEDs, the Hall has tacitly endorsed the writers’ stance that none deserves crossing the 75 percent threshold for induction, which is its prerogative. If the Hall wanted users in, it would give guidance that helped steer the players toward the 75 percent. That looks unlikelier than ever with the new rule.

And so the Hall basks in the afterglow of its wonderful ceremony, ceding the spotlight to the big names and the ...

8. Secondary market that continues to gurgle beneath the stars threatening to get dealt.

Texas is full of possibilities, barreling its way toward the No. 1 overall pick in the 2015 draft – Will it be Duke ace Michael Matuella or Daz Cameron, the dynamic high school center fielder and son of Mike? – and wondering how to chase the Joakim Soria and Jason Frasor deals. Does it triple down on relief help by shipping out reclamation-project-made-good Neal Cotts? Can it extract enough value out of Alex Rios (signed through 2014 at $12.5 million with a reasonable $1 million buyout on a 2015 option at $13.5 million) to head into 2015 with a hole in right field to match its ones at catcher and designated hitter? Considering the Rangers’ 60-day disabled list is an All-Star team – Prince Fielder, Matt Harrison, Derek Holland, Martin Perez, Jurickson Profar and more – any sort of dump at this point is warranted.

Cleveland finds itself in an interesting situation, only 3½ games back of the wild card but with five teams ahead of it, and with a market developing for shortstop and free agent-to-be Asdrubal Cabrera. It’s not bustling, but it does exist, and with veteran Mike Aviles and stopgap Jose Ramirez – not to mention top prospect Francisco Lindor at Triple-A and more than ready to play in the majors at 20 years old – the Indians could flip Cabrera in a big league-for-big league swap to make a run at one of the wild cards.

Sometimes all it takes is a little upgrade, which makes the cases of ...

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In a lost Red Sox season, it may make sense for Boston to keep Koji Uehara. (AP Photo)

In a lost Red Sox season, it may make sense for Boston to keep Koji Uehara. (AP Photo)

9. Andrew Miller and Koji Uehara so interesting. Both are free agents this offseason. Both are in the midst of big seasons. And while Miller is almost assuredly a goner in free agency, likely to settle somewhere in the three-year, $18 million deal that has become de rigueur for the best left-handed relievers on the market, Uehara presents an interesting case for Boston.

Would the Red Sox actually give him a qualifying offer for around $15 million? It’s a rather ludicrous conceit to give any one-inning-at-a-time pitcher a quarter-million dollars an inning, but the Red Sox want to reload for 2015, and their bullpen is positively bereft of a closing candidate. With the best closers fetching at least $10 million a year in free agency, getting Uehara for a year, and not being stuck long-term with something as historically volatile as a relief pitcher, is not the sucker bet it may seem.

So while Miller will take his fastball and slider elsewhere and get Boston another prospect to add to its loaded system, Uehara may well stay put and allow Boston to exert over him the sort of control it long ago relinquished when ...

10. Jon Lester laughed at the Red Sox’s initial contract offer. The Red Sox knew he thought of himself in the Hamels-Zack Greinke (six years, $147 million) echelon but that the Homer Bailey contract (six years, $105 million) was a far smarter starting point if the team was truly serious about extending Lester.

They weren’t. Not then. Not now. Not going forward, as they recognize no matter how courteous Lester is publicly, the ill will from this whole process – from the fashion in which this entire process has turned into a season-long story while Max Scherzer’s contract situation is but a footnote – exists and will come to a head once free agency hits.

Boston punted its advantage, and its best hope at this point is that the pull of the two championship rings he owns – of the memories created in a great baseball city – somehow lure him back. Because right now, with the trade deadline imminent, the best play is to bid him adieu. It’s the only way left to win a losing hand.

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