Should The Red Sox Trade Jon Lester?

It came out on Monday night that the Red Sox and Royals have been discussing a trade of starting pitcher Jon Lester for super prospect outfielder Wil Myers. Myers is no standard-issue prospect, though, as he ranked #28 in Baseball America's top 100 heading into 2012, despite an injury-plagued 2011, and made good on that by hitting .314/.387/.600 across Double- and Triple-A. He will be all of 22 years old in 2013, and is without a doubt one of the best-hitting prospects in the minors right now.

Myers would come with all of the standard caveats for prospects. He's never played in the majors, so it's tough to say just how his bat will work there. A former backstop, he's still working his way towards handling the outfield at the level that's needed for the majors. As said, though, these are standard caveats: it's hard to be excited about Boston's future, a future that includes Jackie Bradley, Xander Bogaerts, and many other prospects, without being equally (or even more) thrilled with what Myers' potential holds.

Myers could be Boston's top prospect for many experts, with Xander Bogaerts the only potential stumbling block to that. He's also arguably major-league ready now, or at least could be called up once enough time has passed in 2013 in order to squeeze an extra season out of his service time. That would give Boston either six or seven years of service, depending on when he's summoned, with the first three coming in at the league minimum. Myers could be a potential answer for the club in the outfield not just in the present, but for years to come, ahead of and alongside the wave of youth that Boston is so invested in.

The cost for this would be Lester, a lifelong Sox hurler coming off of the worst year of his major-league career. There are reasonable arguments to be made on both sides (many of which Alex Speier has already discussed over at WEEI) for keeping Lester or dealing him. For those in favor of keeping him, 2012 was just the one year, and there were signs towards the end of the season that he had begun to figure out his mechanical issues, restoring his erstwhile command. Reunited with John Farrell, the process might be sped up further, and even if he doesn't return to his peak form, he would still be a highly valuable piece of a rotation in need of just that thing.

Lester is a free agent after 2014, and that's if Boston picks up his $13 million option. Right now, with just the one poor year in his history, that option is a no-brainer. But what if Lester doesn't rebound as much as he should? History is littered with pitchers who lost their stuff in their late 20s and were unable to ever produce at their peak level once again. If Lester falters in 2013, he's not about to have the trade value he has right now. This is possibly as good as it gets in that regard, with two relatively inexpensive years left, the chance to give him a qualifying offer after 2014 should he merit it, and a realistic shot at a rebound that brings him back to being the pitcher he once was.

Let's say Lester does return to form. There are still just the two years left on his deal, meaning he's more of a piece on the teams that's waiting for the next injection of talented youth than he is part of the latter itself. That would help the Sox greatly now, in their quest to remain competitive while also attempting to rebuild from within. But you could argue, given the hole on the roster in right field, that Myers would help accomplish that, too, and be around for the much-discussed "next great Red Sox team" that features the aforementioned prospects and more.

You could argue that Lester could be re-signed, but at what cost? Right-hander Zack Greinke is currently looking for a seven-year mega-deal. Cole Hamels just re-upped for six years at $144 million. Left-hander Cliff Lee makes $25 million per year from here on out on a deal he signed when he was already in his early 30s. Anibal Sanchez, who is a middle of the rotation arm, is publicly seeking upwards of $100 million on the market this off-season. Even if he doesn't get it (and he probably won't), a Lester that's returned to form certainly could, and that would mean Boston would be looking at re-signing an arm that could cost about $20 million or more per season to retain, during what are likely to be lesser years of his career.

Does Boston want to lock themselves into a pitcher deal that's the size of those contracts they traded away in August? It's unlikely, especially not if they can bring in someone like Myers instead. With the likes of Edwin Jackson, Dan Haren, Brandon McCarthy, and even Anibal Sanchez out there on the free agent market, the Red Sox could fill the void left by Lester at least to a degree in order to help keep the current roster competitive. And, except for with Sanchez, those arms would likely be here only for the duration of Lester's current contract, too, so it'd be a swap of dollars only to fill the hole, with the return of Myers as the reason to make that switch. And while Myers could falter, as many a prospect has before him, there's immense talent there that makes him worth the risk of losing two years of Lester.

There are reasons to deal Lester, and reasons to keep him. It's hard to fault the Red Sox for whichever decision they do make, though, it might work out best for them in the long-term if they send him out for Myers -- imagine, for a moment, an outfield of Bryce Brentz, Jackie Bradley, and Wil Myers in 2015. Of course, there's going to be more to this deal than just Lester for Myers, and that's where things start to get a little more complicated. What is this pitching the Red Sox would get back, given the Royals need Lester to improve their own pitching situation to begin with? Who would be considered the "outfield help" that the Royals would need in return after dealing one of their future outfielders? Those are the questions that need to be answered before any deal can occur, and as of now, there's nothing out there to suggest the two clubs have even gotten that far in their conversations.