Red Sox, Royals Discuss Jon Lester - Wil Myers Swap

Rob Bradford is reporting that the Red Sox and Royals discussed a potential Jon Lester - Wil Myers swap, as well as the opposite trade where the Sox would provide "outfield help" in exchange for pitching.

It's a...provocative idea, to say the least. A team already struggling to fill its starting rotation with quality drops their best arm from 2008-2011 to fill an outfield spot? It almost seems like it's taken straight from the book of Bard to the rotation and Reddick to Oakland, and on some level it is. And that's what makes me think there's actually something too this, because it does seem like a very Cherington move.

For the record, no, I don't need to be reminded that the aforementioned moves were absolute disasters. Reddick put on a power-and-defense show in Oakland, Bailey provided half a season of tears (and that's the half he pitched!), and Daniel Bard was lost at sea or something like that. But that doesn't mean any move in the same vein--dealing from a position of need that can be filled in FA to fill a position of need that is more difficult to--is a bad idea.

Consider what the Sox actually lose and gain in the event that they do trade Lester for Myers. Going to Kansas City is a one-time great arm who saw a bit of decline towards the end of last season and a big decline in 2012. He can certainly come back--all the way back, even to 2009-2010 heights. He has two years remaining on his deal, including a club option, but will still cost $24.5 million total. Gone are the days where Lester was a sure thing on the cheap. Now he's a question mark at an average price, even if his tax figure comes out at about half that price.

Coming back would be one of the game's premiere hitting prospects in Wil Myers. An outfielder who could bring serious pop to Boston's outfield, Myers clubbed 37 homers in the high minors last year at 21 years of age. If he's not ready for the majors yet, he's doing a fine job of pretending to be. As with any minor league player, however, there are questions with Myers, particularly how his glove will fare in the outfield, and if he'll get his strikeout numbers down.

Of course, when presented with two guys with about equal question marks, it probably makes sense to go for the one with higher upside, and Myers is that guy all the way given his age and contract situation. The hope with Lester is that he'll provide a couple good years in the rotation and maybe sign an extension. The hope with Myers is that he'll be an anchor for the outfield for about a decade, with six years guaranteed.

As a result, it's not terribly surprising to find that the general opinion of this deal from the outside is that the Royals would be crazy to do this. And, frankly, they would. The only reason the Red Sox wouldn't pull the trigger here instantly is because of Lester's name recognition in Boston and their particular circumstances re: the rotation. And, yes, it's also true that, given how barebones the details on the talks are, it's quite possible that the Royals aren't terribly interested.

On the other hand, Dayton Moore. Jonathan Sanchez, Ervin Santana, Gil Meche, Gil Meche, Gil Meche. Moore has a long history of making questionable moves involving starting pitchers. And if I'd told you five months ago that the Sox would trade Carl Crawford, Josh Beckett, Adrian Gonzalez, and Nick Punto and actually get legitimate prospects in return, you probably would have laughed in my face. Anything can happen, and frankly, given the individuals involved, it wouldn't be all that surprising if this trade did go through.

So let's say the Sox send Lester to Kansas City and get Wil Myers back. Now what? Now they've got an even bigger hole in the rotation. The good news is their outfield is set--one of the spots in the very long term--as well as another $11.5 million off the payroll and a guaranteed spot in the rotation. The latter, for the record, is not an insignificant commodity. If Lester was a question mark, he was one they couldn't exactly replace with a more solid option thanks to the lack of rotation spots they had to offer legitimate options.

While we've all been wanting the Sox to avoid long-term contracts, there's something to be said for how financial flexibility allows for risks to be taken. With another contract off the payroll and a guy like Myers secured as a cheap long-term option, signing a guy like Anibal Sanchez long-term doesn't seem nearly so dangerous. Myers would also allow the Sox to trade from their minor league outfield depth to pick up another starting pitcher--say New York's Jon Niese, for example? Unfortunately, the situation surrounding their top outfield prospect, Jackie Bradley, is muddied by the question over whether Jacoby Ellsbury will be here in the future..Still, even if he's not, Bryce Brentz could be a part of a bigger deal.

There are a lot of steps between preliminary conversations and anything concrete, to be sure. But if for no other reason than that this is Dayton Moore, there's reason not to dismiss it out of hand. And should this eventually come to pass, even if it seems to be moving away from the direction the Sox need to head, there will probably be more shoes to fall behind it.