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Wednesday, July 16, 2014
Updated: July 17, 2:32 PM ET
Pondering futures of Lester, Uehara

By Gordon Edes
ESPNBoston.com

All-Star inspired musings about Jon Lester and Koji Uehara, while anticipating that the engagement of Will Middlebrooks to Jenny Dell may soon be dwarfed by the renewal of vows between the Red Sox and Lester:

• The Sox left-hander once had an irate John Farrell pounding the table in opposition to a trade that would have sent a then-emerging pitcher to the Minnesota Twins for a two-time Cy Young Award winner, Johan Santana. Funny thing about that proposed deal, one that plenty of Red Sox fans would have made for the pitcher widely regarded as the best left-hander in the American League, if not the game.

Jon Lester
Jon Lester has held up over time, which suggests he might be an exception to the old adage about high-priced, aging pitchers.

Santana was 27 when he won the second of his two Cy Young Awards. He was 29 when he last made as many as 30 starts in a season or threw as many as 200 innings, 29 when he last struck out as many as 150 batters, 29 when he last won as many as 15 games in a season. And yet, from the ages of 30 to 35, though he missed two full seasons in that time and parts of a third, he has been paid in excess of $116 million by the New York Mets.

John W. Henry surely can recite those kinds of figures from memory. Just as he can probably tell you that CC Sabathia's ERA has climbed from 3.30 when he was 30 to 4.01 when he was 31 to 5.20 when he was 32 to its current 6.07 at age 33, and his WAR has gone from 7.5 at age 30 to a minus-0.4 this season. He has been paid $69 million in that time, and is due at least another $48 million. Injuries have taken their toll on both of those pitchers, but that's the point: As former pitcher-turned-broadcaster Dirk Hayhurst wrote recently in a wise and perceptive look at pitching injuries:

"Pitching isn't an injury waiting to happen, it's an injury happening. Some players break faster than others. Some never break. But that's the symptom, not the disease. Pitching is a dangerous activity, and as bodies are trained to throw harder and generate more power, that danger goes up."

Lester, a cancer survivor, has held up well in the course of his Sox career, and is enjoying arguably his best regular season ever after an absolutely dominating postseason performance last October. The Sox can ill afford to let him walk in three months, which is why there are less than subtle signs that they are preparing an offer much more in line with the current market standards. They have always maintained that while they want to break from mindlessly dispensing contracts of inordinate length, there are exceptions. Lester is clearly one of them. Whatever self-inflicted damage they caused with low-balling him this spring appears easily remedied with a man who sang of his love for all things Red Sox this week in Minneapolis. Accept the risk, name the right number -- a number that may well have gone up since March -- and schedule the news conference.

Distraction? It's not as if Lester's negotiations will distract from a playoff race.

SportsNation

Do you think Jon Lester will be pitching for the Red Sox beyond this season?

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    59%
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    41%

Discuss (Total votes: 9,862)

• Lester has nine wins at the All-Star break. If he matches that number after the break, here are the pitchers he will pass on the Sox's all-time victory list: Bob Stanley, Smoky Joe Wood, Pedro Martinez. Another nine wins would give Lester 118 in his Sox career. That would leave him within five wins of passing Luis Tiant, and six wins of passing Mel Parnell to become the winningest left-handed pitcher in Sox history. Only Roger Clemens and Cy Young (192 wins apiece) and Tim Wakefield (186) would be ahead of him. Average 15 to 16 wins a year over the next five years, and he stands alone. Greatest left-hander in Sox history? In WAR, only Lefty Grove (44.7) is still ahead of Lester (30.6), and there's also Lester's October portfolio to consider.

He has made a home for himself here, and has carved out a place in history here that he cannot match anywhere else. Seems odd to say it, but his greatness has almost sneaked up on Boston. Before the 2013 season, there was uncertainty on whether the Sox would exercise his option. Now he's indispensable. "Great" is a word that might stick in the throats of some observers. They'd prefer the needle stop at "very good." But the performance speaks for itself.

• Boston's other All-Star, Uehara, represents something of a test case on whether the Sox are truly committed to building for the future. A strongly opinionated reader, who calls himself "Larry Larry," has visions of cutting the kind of deal the Texas Rangers, non-contenders at the time, made in 2003 for closer Ugueth Urbina, when they acquired three prospects from the Marlins. Will Smith never made it to the majors; Ryan Snare played one game. The third prospect in the deal? Adrian Gonzalez. The Rangers gave up on him too soon him and dealt him to the Padres, where he became an All-Star.

Uehara, "Larry Larry" argues, should command a similar haul. The one thing that might tamp down Uehara's market is the fact contenders will have other closers to choose from, including Huston Street of the Padres and Jonathan Papelbon of the Phillies. Papelbon will cost a team only money; Street is having a terrific season in an up-and-down career. Uehara is the current gold standard, even at age 39 and with limited shelf life. He is a proven difference-maker in October. The Sox should aggressively market him and see what they can turn up.

SportsNation

Will the Red Sox -- winners of four of five before the All-Star break -- play their way back into the playoff race?

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    48%
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    52%

Discuss (Total votes: 23,375)

• Finally, had to smile at the recent ESPN SportsNation poll asking whether the Red Sox can play their way back into playoff contention. The admittedly unscientific poll is close, with a narrow 51 percent majority voting yes, but New England was a solid bloc of red voting no in a geographical breakdown of the results. The one exception was Connecticut, where Yankee fans might have been taunting the Sox with false hope. The current ESPN standings place the Sox's odds of making the playoffs at 2.4 percent. The first-place Orioles, if they play .500 ball the rest of the way, would finish with 86 wins. The Sox would have to play at a .642 clip (43-24), which is better than any team in baseball has played to date this season, to finish with 86 wins. To win 90 games, the usual target for postseason inclusion, the Sox would have to play at a .701 pace (47-20).

Folks like to point to how the Rays began September 2011 nine games behind the Red Sox and overtook them for a playoff spot. But that was more about the Sox collapsing (7-20) than the Rays surging. An awful lot of teams would have to collapse in front of the Sox, whose record at the break is better than only those of the Rangers and Astros.