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Why the Red Sox Should Trade Jacoby Ellsbury, Jon Lester This Winter Too

Rick WeinerFeatured Columnist IVJune 26, 2016

Why the Red Sox Should Trade Jacoby Ellsbury, Jon Lester This Winter Too

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    Virtually every player in baseball gets put on revocable waivers at one point or another following the non-waiver trade deadline at the end of July, so this shouldn't come as a surprise to anyone:


    Jon Lester and Jacoby Ellsbury are the latest Red Sox to be placed on trade waivers.

    — Nick Cafardo (@nickcafardo) August 24, 2012




    After moving the un-movable contract of Carl Crawford, along with Josh Beckett, Adrian Gonzalez and Nick Punto for a plethora of prospects—and James Loney—it would be naive on anyone's part to think that Red Sox GM Ben Cherington is done wheeling-and-dealing.

    While more moves are likely going to wait until this winter, one thing is clear—the Red Sox are open for business—and with that being said, neither Jacoby Ellsbury nor Jon Lester should make any long-term plans in Boston this winter.

Jacoby Ellsbury...the New Grady Sizemore?

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    Injuries have limited 28-year-old Jacoby Ellsbury to less than 50 games this season, and while he showed a very high ceiling in 2011, this marks the second time in three years that he's missed significant time due to injury.

    If this story sounds familiar, it's because we've seen it before—only it was in Cleveland, not Boston, and the player in question was Grady Sizemore, not Ellsbury.

    It's impossible not to see the parallels between the two—and that's not a good thing for Ellsbury or his fans.

    Ellsbury makes about $8 million, and has one more year of arbitration left on his contract. He is set to become a free agent at the conclusion of the 2013 season.

    With Jackie Bradley working his way through Boston's farm system—he's currently at Double-A—Ellsbury's eventual replacement isn't far away from prime-time as it is.

    Injuries aside, Boston's best move would be to move Ellsbury while he's still under team control for another season and has substantial value around the league.

Jon Lester...the New Tim Hudson?

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    For your consideration—the statistics of both Jon Lester and Tim Hudson from the season they turned 24 through the season they turned 28 (which Lester is still playing out):

    Hudson: 81-37, 3.31 ERA, 1.21 WHIP, 6.3 K/9, 2.40 K/BB

    Lester: 73-42, 3.60 ERA, 1.26 WHIP, 8.5 K/9, 2.73 K/BB

    Pretty close, aren't they?

    Oakland traded Hudson to the Atlanta Braves following the 2004 season, and while the players that they acquired didn't pan out as they had hoped, they did pick up three prospects in exchange for a pitcher who never achieved the same level of success as he did with the A's.

    Lester, who is owed $11.625 million in 2013 and either a $250,000 buyout or $13 million for the 2014 season, still has substantial value around the league.

    With Clay Buchholz under team control through at least the 2015 season and promising youngsters in Felix Doubront and the newly acquired Allen Webster and Rubby De La Rosa, the Red Sox have a number of intriguing options for the starting rotation over the next few seasons.

    Moving Hudson was the right move for the A's at the time, regardless of how the return they got played out.

    Moving Lester would not only continue to clean out those who have been perceived by some to be "bad apples," but it would bring back multiple pieces for the Sox to use as they continue to re-tool and re-build on the fly.

The Boras Factor

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    In, convincing the Dodgers to pick up nearly all of the salary owed to the four players that Boston sent west over the weekend, Boston freed up a ton of cash for them to re-sign their own players, sign free agents and take on salary in trades.

    When it comes to re-signing Jacoby Ellsbury, there are a few things to take into consideration.

    First, does Ellsbury actually want to play in Boston?

    There are generally two points of view on the subject.

    One side says that he cannot wait to get out of Boston—that between the market itself and his disgust with the misdiagnosis of his five broken ribs two years ago, Ellsbury has had his fill of Beantown.

    The other side—and per the Boston Globe's Nick Cafardo, this side includes those infamous "unnamed team sources"—Ellsbury loves Boston, he loves playing for Bobby Valentine, and his preference is to work out an extension with the team.

    Of course, the truth probably lies somewhere in the middle.

    But does what Ellsbury wants really matter?

    He's represented by Scott Boras, and while Boston and Boras have worked together many times before, we can be sure of one thing—virtually none of his clients sign extensions before they hit the open market.

    Boras is the master of leveraging teams against each other, even when the reality of the situation is that there's only one team involved.

    So while Boston will have the available resources to match any offer, no matter how ridiculous it may be—would they?

    We talked about Ellsbury's injury history before, and the fact that players like Jackie Bradley are working their way through Boston's farm system.

    It's no sure thing that the Red Sox would look to re-sign Ellsbury should the money get out-of-hand—and it's far better for them to strike while the iron is hot rather than hope that a potential compensatory draft pick works out years down the road.

Changing the Culture

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    Whether it's the players, the coaches or a combination of the two, there's no question that the atmosphere around the Red Sox has been, shall we say, tenuous, for quite some time.

    Regardless of what the players on the team say—because let's be honest, they are going to cover themselves and not risk another "rat" episode at this point—things are not all peaches and cream inside Boston's clubhouse.

    When you look at the "old guard", guys who have been a part of the team for awhile, only Dustin Pedroia stands out as someone you don't want to lose. He's the glue, the heart-and-soul of the team and the unquestioned leader of men.

    After that, you have a foundation of youth: Pedro Ciriaco, Felix Doubront, Ryan Kalish, Ryan Lavarnway and Will Middlebrooks to build around.

    Everyone else on the roster is expendable—and replaceable.

    While Red Sox Nation, like Yankees Universe or any other clever moniker you want to bestow upon the ravenous fanbase of a perennial contender expects their team to compete for a World Series year in and year out, you aren't talking about a group of clueless buffoons either.

    They can see that the team isn't going anywhere the way it's currently constituted.

    They're willing to let the Red Sox atone for their mistakes and make the moves necessary to ensure a competitive ballclub for the next decade.

    The only question is this—will the organization finish cleaning house, putting the team in a better position heading into 2013 than they have been in years?

    Or will they revert to bad habits, throwing good money after bad in a feeble attempt to try and buy their way back to contender status?

    In the words of the immortal Judge Smails: "Well...we're waiting!"

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