Enough has been said and written about Jon Lester’s contract negotiations with the Red Sox that there is no need to rehash here. The Red Sox, for their part, didn’t expect to be this bad in 2014, so they probably believed another season of contention would give them more time and allow cooler heads to prevail in talks on a new contract with Lester this offseason.

Instead, Boston sits in last place in the AL East with a worse record than the White Sox, Mets, and Marlins as the trade deadline arrives. Lester has gone on to have a career year, and now the Red Sox hold one of the deadline’s biggest trade chips without any guarantee they can re-sign him to an extension.

Which is why the chances that Lester will be traded before Thursday’s deadline have grown increasingly likely. Ben Cherington can’t afford to let Lester walk away and only receive draft-pick compensation in return as the club tries to recover from the ruins of a disappointing season. As tough as it is to deal the nine-year Boston veteran, Lester will yield the Red Sox some legitimate prospects, and hopefully the type of young outfield bat the club desperately needs.

(Photo credit Kelly O'Connor of sittingstill.smugmug.com.)

(Photo credit Kelly O’Connor of sittingstill.smugmug.com.)

What this means for the Red Sox’s rotation is less clear. Lester has been the second-best starter in the AL this year, and healthy, dependable, top-of-the-rotation lefties don’t grow on trees. The club’s highly praised pitching depth in the upper minors will surely help, but if the Red Sox expect to contend again in 2015 (something they have repeatedly stated is the case) Clay Buchholz, John Lackey, and three or four youngsters shouldn’t be depended upon to lead them back to prominence.

Buchholz has been a mess this season, showing no signs of his lights-out form from 2013. Lackey, meanwhile, will make $500,000 next year and asking a proud, hard-working veteran like Lackey to pitch on that salary as one of his close friends in Lester walks away without a contract is presumptuous at best.

And while Rubby De La Rosa, Brandon Workman, and Allen Webster have shown glimpses of effectiveness, they won’t be mid-rotation starters on a playoff team at this juncture. The same goes for fellow pitching prospects Anthony Ranaudo and Matt Barnes. Henry Owens, Boston’s best pitching prospect, doesn’t quite have the ceiling his Double-A numbers might suggest, and he will need some more seasoning in Pawtucket before contributing in the majors anyhow.

So how should the Red Sox go about replacing Lester, then, assuming he signs elsewhere this winter?

Rumors have cropped up within the past week that Boston could pursue Phillies left-hander Cole Hamels this offseason. Given what Philadelphia is asking for Hamels at the deadline, though, that seems like an expensive and unnecessary proposition. Why let Lester, who is the same age as Hamels, walk and then turn around and trade multiple prospects for a pitcher whose contract will pay him within the same range that Lester is asking for?

Reigning AL Cy Young Award winner Max Scherzer will be a free agent this winter, yet he rejected a lucrative extension offer from the Tigers this spring that would have made him one of the seven highest-paid starters in baseball. Considering Boston is reluctant to pay Lester fair market value, seeing Cherington hand Scherzer a gargantuan, long-term contract would be surprising.

This offseason’s other top pitcher, James Shields, represents a lower-cost option for a Red Sox front office that is clearly reluctant to spend big on players in their thirties. Shields will turn 33 in December, but won’t cost anywhere near what Lester or Scherzer will; nor will he be seeking the type of five-to-six-year contract Boston has made a point of shying away from in free agency. Shields has been one of the AL’s most consistent and durable pitchers dating back to 2007 and also comes with years of experience in the AL East.

Pairing Shields with another lower-cost free-agent starter, such as Hisashi Iwakuma or old friend Justin Masterson, might help give the Red Sox needed rotation depth and allow them to add two starters for roughly the same type of money Lester and Scherzer will command on the open market.

The Red Sox will also likely make a trade or two this offseason given all their depth down on the farm and their need to improve at the major league level. How Cherington balances all these moving parts and who Boston can acquire before Thursday’s trade deadline will go a long way in determining where the club needs to upgrade in the offseason.

Letting Lester walk isn’t a disaster by any means. But the Red Sox can clearly afford to spend money, and that is something they must do if a trip back to October is a legitimate goal next season. Handing out multi-year contracts to starters in their thirties is by no means a slam dunk, which makes an expensive, long-term deal for Lester a more difficult proposition than some might suggest.

Failing to use the money saved on missing out on Lester would be a far bigger issue, and one worthy of the criticism the Red Sox have already begun receiving in the wake of Lester’s imminent departure.