Trade deadline Wednesday: Dreaming of Jon Lester

This is where things stand on the Jon Lester front at ~10:00 AM on Wednesday, July 30th: the Red Sox have announced that he won’t make his scheduled start tonight, and while a trade isn’t done and no one knows where Lester will end up, it probably wouldn’t be unfair to characterize an eventual Lester trade as “imminent.” Ken Rosenthal reported last night that the Pirates, Cardinals, and Dodgers were all in the mix, while Sean McAdam later added that A’s, Orioles, and Blue Jays are also interested, though the Sox seem likely to trade Lester to the National League. Really, that’s all we know right now.

It’s really hard to tell where things will go from here. If you assume the Pirates, Dodgers, and Cardinals as the three main suitors, then the Dodgers are certainly the wild card of the bunch that’s most likely to pay wildly for a rental, but then, they also have the worst farm system of the three teams. If you do assume these three teams as the finalists (which is not necessarily wise; the fact that Lester’s scratched tonight and that these three teams seem to have emerged as the top contenders to land him might be a public negotiation tactic with the Red Sox and someone else), it might not be a leap to say that the final return for Lester won’t be exorbitant. The Cardinals and Pirates are unlikely to do anything alarming over a two-month rental, and while the Dodgers might, they’re also less able to do so.

If that is indeed the case, then yesterday’s Yahoo! report that the trade was centering on Josh Bell and Rob Biertempfel’s guess that it would take two of the Pirates’ top ten prospects is probably a good guide to what a Lester-to-the-Pirates trade would look like. Biertempfel guessed Bell and Glasnow, but I think it’s almost unfathomable that the Pirates would trade Glasnow for a rental. In fact, if the deal does center on Bell, then I don’t think that any of the Pirates’ other prospects that landed in Baseball America’s mid-season Top 50 (Glasnow, Jameson Taillon, Austin Meadows, and Nick Kingham) would be part of the deal, and I might extend “untouchable in this context” status to Reese McGuire and possibly Alen Hanson (Hanson is more or less the Pirates’ only high-level middle infield prospect, but I still can’t figure out what the Pirates really think of him [UPDATE: Actually, JaCoby Jones’s breakout year means that Hanson is not the only middle infield prospect that the Pirates have, which probably makes Hanson more tradable. Or makes JaCoby Jones tradable, since he’s pretty good. Or maybe middle infield prospects are important and you shouldn’t trade them at all because many good players of all stripes begin as middle infield prospects, because they’re hard to be redundant. We’re way off-topic now.]). That’s not to say that the Pirates wouldn’t consider trading any of these guys under any circumstance; it’s to say that if the Pirates are trading for two months of anyone, that I don’t see them putting Josh Bell and one of these players into the deal. Glasnow, in particular, is interesting trade bait to discuss because his numbers are so astronomically good and the questions about his control and secondary stuff are real, but I think Glasnow has far too much value to be traded for a rental. They might make a trade including Bell and one of these other players, but that seems foolhardy and the Pirates don’t often do things that seem foolhardy.

All of this being said, I am starting to warm to the idea of building the deal around Bell and some lesser prospects. That’s mostly stemming from one thought: Josh Bell is the Pirate prospect that’s most likely to be traded anywhere. That’s less a judgment on Josh Bell than it is on the circumstances; the Pirates have three very good young outfielders in Pittsburgh under their control for years and Josh Bell is going to be big-league ready while those three will all likely still be Pirates. On top of that, even if the Pirates trade Bell, they would still have Austin Meadows (who won’t be traded due to his injury this year) in the low minors and they would probably still have Willy Garcia, who has 14 homers and a .491 slugging percentage as a 21-year old in Double-A. In effect, the Pirates’ minor league system is still so good that they could trade Josh Bell and barely even notice that he’s missing, and that’s a reflection on the Pirates’ system and their depth in the outfield without being even the slightest reflection Bell as a prospect.

That means that the question could be rephrased like this: Is trading for two months of Jon Lester the best use of Josh Bell’s trade value? That is an awfully difficult question to answer. On the one hand, it’s easy to see how Bell could be traded in the off-season to shore up a long-term position of need; say, for example, a trade with the Diamondbacks built around him and Didi Gregorius(1). Gregorius might offer an upgrade of a win or two over Jordy Mercer (again, up for debate, just roll with me) and he’d do it over the course of several years. Lester offers an upgrade of a win or two over Vance Worley/Edinson Volquez and then he’s gone, but the true value of Lester’s one or two wins is huge. Look at the playoff odds page at FanGraphs this morning. They project the Brewers to finish with 85 wins, and the Pirates and Cardinals with 86. They’ve got the Giants at 85, the Braves at 86, and the Nationals at 90, and the Dodgers at 91. Quite literally, Jon Lester’s input to the Pirates might be worth the difference between them making the playoffs or not making the playoffs, or the difference between them winning the NL Central or being a wild card (which could, in effect, be the same as the difference between making the playoffs or not making the playoffs). Obviously it’s possible that they could trade for Lester and end up nowhere, and that’s the huge risk that they’d be taking, but it’s very much worth considering the context in which the small upgrade (in terms of total win value, obviously he’d be a big upgrade over the back end of the Pirates’ rotation in terms of talent) that he would provide for them. 

And still, I’m torn over this idea. I’ve got this feeling in my gut that this Pirate team in particular is capable of something big in a way that last year’s team wasn’t and that Lester pushes them to a different level, and I’ve got my head telling me that that’s just the natural evolution from being a fan of a perennial doormat to being a fan of a team with expectations. And my head continues on: Even if this particular swap might make sense, the general precedent of trading a good prospect for a rental player is a slippery slope to go down and depleting minor league depth for minimal value is treading in awfully deep water and the general principle of the idea behind this trade is just hugely dangerous territory for a team with the Pirates’ lot in life. And then my gut punches back with a images of Lester, Cole, Liriano, and Morton starting a seven-game playoff series and my head admits that that’s pretty tempting, all things considered, and now I’m almost 1300 words into this post, through a cup of coffee, with experiments running in the background, and I still don’t know what my final opinion would be if this trade went down. And this is all without even beginning to consider that a Bell-for-Lester swap would probably be a much larger deal involving more Pirate prospects and probably a reliever from Boston, and that my grappling with the idea of Bell-for-Lester only begins to grasp what a final trade would probably look like.

There are 30 hours left until the trade deadline. They will probably be 30 long hours.

1 – This is literally just 100% spitballing on my part without much thought at all, I’m only making an example of the sort of trade the Pirates could use Bell in, not necessarily what I think the should do with him if they don’t trade him for Lester or what I think fair value would be for him.

Image: Jared Tarbell, Flickr

Pat Lackey

About Pat Lackey

In 2005, I started a WHYGAVS instead of working on organic chemistry homework. Many years later, I've written about baseball and the Pirates for a number of sites all across the internet, but WHYGAVS is still my home. I still haven't finished that O-Chem homework, though.