Jon Lester Situation Forcing Red Sox Into Big Payout One Way or Another

This article was originally published at SportsReelBoston.com.

Having recently endured a ten-game losing streak that saw them tumble briefly into the basement of the American League East, the Boston Red Sox have many concerns about the here and now- even after winning their next four and counting. The future of impending free agent starting pitcher Jon Lester should be an area of major worry, as no matter what happens with him, the team is faced with a situation that is almost certain to result in huge payout of one kind or another.

The 30-year-old left-handed Lester is one of the best pitchers in Red Sox history. In a nine-year career, he has gone a combined 105-62 with a 3.74 ERA and 1,320 strikeouts, serving primarily as the team’s ace. He has done so with class and dignity that began with his ongoing successful bout with cance as a youngster. That and the two World Series titles he has won with the team—including going 3-0 with a 0.43 ERA in the Fall Classic has earned him the admiration of Red Sox Nation.

Sadly, there is a chance that 2014 could be Lester’s last season in Boston. He is due to become a free agent this winter and seems destined to hit the open market. Although ESPN.com’s Dan Szymborski wrote an article (subscription required) projecting that the southpaw is worth potentially as much as a six-year, $145 million contract, Lester previously indicated he might be willing to take a bit of a hometown discount to remain with the organization that drafted him.

It turns out that hometown discount is one of those relative terms that can mean different things to different people. That became apparent when Fox Sports’ Ken Rosenthal reported earlier this season that the Red Sox offered Lester a four-year deal in the neighborhood of $70-$80 million- which was not accepted.

With Lester facing the possibility of making Kardashian money this offseason, the Red Sox have a situation where they are almost definitely going to have to lay out a ton of cash. If not for their lefty, then for his replacement, as his departure would leave a gaping hole at the top of the rotation.

Currently, the Red Sox have Clay Buchholz, John Lackey and Felix Doubront as starters under contract for 2015. Lackey and Doubront have proven they can be mid-to-end of rotation hurlers, but they are not guys who profile as number ones.

Buchholz has ace potential, but has battled injuries and inconsistency throughout his career. At 2-4 with a 7.02 ERA thus far in 2014, he is currently on the disabled list and may not even be in the rotation much longer if he doesn’t turn things around when he returns.

Boston has some intriguing pitching prospects like Brandon Workman, Allen Webster, Matt Barnes, Anthony Renaudo and Henry Owens, but none of them are sure things (or necessarily aces) and some still need some time down on the farm to get major league-ready.

Simply put, if the Red Sox don’t bring Lester back, they will need to find an ace somewhere. As one of the majors’ frontline franchises, they expect to compete every year. There is no realistic way to do that without a strong starting rotation that needs a proven horse at the top.

Lester could absolutely be on the level when he says he might take less money to remain in Boston. On the other hand, it’s unlikely that he will shortchange himself too much with the potential riches at his grasp. As a battle-tested lefty with years of success under his belt, he should have a plethora of teams laying out an assortment of their finest wines and cheeses to try and lure him away.

Unfortunately, once the words “hometown discount” have been uttered by a player, that usually holds to a ridiculous standard that portrays them as somehow selfish if they don’t sign a below-market deal. Lester should not be thought of in that way if he chooses to take the deal that suits him best. He is at the peak of his career and has set himself up to capitalize on the hard work he has invested in his career. He has earned the right to maximize his value—the same expectation anybody would have in their work life—from a doctor to a waiter.

It will be shocking, especially given the recent fiery hot pitching market, if Lester is signed for any less than $130-$150 million—and possibly even more. There is no scenario where the Red Sox can avoid cracking their checkbook open like the tomb of Lazarus if they wish to retain their ace.

Even if Boston determines Lester is too rich for their blood, they will facing a similarly high price to find his replacement. Max Scherzer, James Shields and Justin Masterson are the current best starters expected to be free agents this fall. Despite varying ages and levels of prior success, they have all pitched at the front of rotations, and will never have to shop the discount racks again.

Pitchers like David Price and Jeff Samardzija may be available in a trade but would require a boatload of premium prospects for their current respective teams to agree to give up such talented horseflesh. With one of the best farm systems in baseball, the Red Sox have the pieces to make just about any deal happen. However, doing so could be the equivalent of robbing Peter to pay Paul. While their rotation could be shored up in the short term, the price tag could be the future security of a self-sustaining organization suffering a major blow.

Lester may return to Boston and he may not. The entire situation is completely up in the air. However, something that is as plain as the nose on your face is that the Red Sox are going to be paying big this offseason- one way or another. The only real say they have is who is going to be on the receiving end of their checks and/or their prospects.

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