Jon Lester Makes Sense for the Pirates

The Pittsburgh Pirates don’t have much of a recent history of buying. This is because the Pirates don’t have much of a recent history of winning. But the team was somewhat active during each of the past two seasons. In the middle of 2012, the Pirates added guys like Wandy Rodriguez, Gaby Sanchez and Travis Snider. In the middle of 2013, they added guys like Marlon Byrd, Justin Morneau, John Buck and… Robert Andino? The Pirates were happy to make some tweaks, but they didn’t want to do anything too big, because they’ve been thinking longer-term. They haven’t been positioned to give up prospect talent.

Well, it’s 2014. And the Pirates are good again. They’ve been rumored to be in the mix for some smaller bits, but Tuesday brought word of a potential blockbuster:

The Pittsburgh Pirates are a fast-emerging dark horse in the Jon Lester sweepstakes, joining the Los Angeles Dodgers in pursuit of the Boston ace as the Red Sox decide whether to trade him before Thursday’s deadline, major league sources told Yahoo Sports.

Lester’s a big fish. Arguably the biggest fish out there. He’s also a rental fish, in whatever kind of market it is where you rent fish. The Pirates haven’t previously targeted moves like this, but this season not only are they in the mix — they seem like a perfect match. The Pirates check off all the boxes on the Jon Lester trade-partner checklist.

Competitive team

Let’s start with the obvious one. It wouldn’t make sense for the Houston Astros to trade for Jon Lester because the Astros are terrible. Lester’s a stretch-run rental, and at this writing, the Pirates have seven more wins than losses. They’re not far back from having the best record in the National League, and they project to win more than half their games the rest of the way. Right now, they’re projected for about the same rest-of-season record as the Giants and Braves, with whom the Pirates are competing. If you flip to season-to-date stat projections, the Pirates look a bit worse, but they’re still in a big pack of pretty good teams, all of which would like to get better in the coming days.

With division and wild-card chances

Teams focusing on the wild card would be made better by adding Jon Lester, but they’d face an excellent chance of not getting to use Lester at all in the playoffs. The playoffs are where a lot of his value could come from, so ideally an acquiring team would have a good path to the Division Series. The page I’m looking at tells me the Pirates have a 28% shot at the division and a 24% shot at one of the wild cards, yielding about a 40% shot at the DS. Lester would only make those odds better, and while he wouldn’t guarantee anything but the existence of Jon Lester Pirates jerseys, every move that’s ever been made in baseball has been about playing the odds, and there’s million-dollar value in improving Division Series odds by several percentage points.

With a need

The Dodgers are looking at Lester too, but that’s a team with Zack Greinke, and Hyun-Jin Ryu, and the best starting pitcher in the world. So while Lester would fit in every rotation, he fits certain rotations better than others. The Pirates, to this point, rank last in starting-rotation WAR, and they’re in the bottom tier in starting-rotation RA9-WAR. They’re projected to have a bottom-tier rotation the rest of the way, and while you can see the upside in guys like Gerrit Cole and Francisco Liriano and Jeff Locke and even Vance Worley, Lester’s better than all those guys. He’d immediately become the staff ace, and he’d be positioned to throw more postseason innings than anybody. He’d get up to two starts in the Division Series. He’d get two or maybe even three starts in the Championship Series. He’d probably get the nod in the one-game playoff, if things lined up right. Few rotations in baseball would be more improved by adding Jon Lester. This isn’t just about Lester replacing the No. 5 for the final two months. It’s also about what he’d mean for a staff in October.

With prospects

According to Baseball America’s midseason top 50, the Pirates have names at No. 21, No. 24, No. 35, No. 37 and No. 43. Marc Hulet’s midseason top 25 gave the Pirates No. 16. The Pirates have prospects you could stomach trading for a guy like Lester. They’ve promoted Gregory Polanco and they’re not going to move him because he’s upper-tier, but there’s a lot of depth remaining of the good-but-not-elite sort. Jeff Passan and Tim Brown reported the Pirates and Red Sox have talked about Josh Bell. Bell was No. 35 on the BA list, and that values him around $20 million – $30 million. Different people will have different interpretations of Lester’s stretch-run value, and some of that depends on how far the Pirates could go, but there’s a lot of sense in a Lester/Bell swap, maybe with another guy coming from the lower end of Pittsburgh’s organizational top 10. On paper it might sting to trade two of your top ten prospects, but the value of guys at the top greatly exceeds the value of guys near the bottom, so really, Lester should cost one good prospect and one talented and intriguing prospect. The Pirates are very well stocked.

With a sense of urgency

The Pirates, right now, aren’t leading their division, nor do they possess one of the wild-card slots. They’re in an extremely tight multi-team race, and this isn’t just a choice between Lester or no Lester; if the Pirates don’t get him, he could instead land with the Brewers or Cardinals, which would make the Pirates worse off. Now, the Pirates are a team that wants to win consistently and sustainably, but we also have to recognize that they’re a lower-budget operation, and teams that don’t spend a lot of money will have greater difficulty contending year in, year out. So there’s a greater incentive to seize the opportunities that do present themselves, and right now the Pirates are in a spot where they could make themselves World Series contenders. There’s no certainty they’ll be back in 2015 or 2016, so this is a time to move.

With limitations

Even if David Price were available, the Pirates probably wouldn’t get involved, because they wouldn’t want to give up that much youth, and they wouldn’t be able to afford Price’s 2015 salary. The same idea applies to Pittsburgh getting Cole Hamels, and word is the Pirates have cooled on A.J. Burnett because of his expensive 2015 option. The Pirates should actually like the idea of a rental, because there’s no commitment for 2015, and the lack of future value and compensation reduces the current asking price. Some teams want to have a guy for more than two months. The Pirates can’t really look for those guys, so Lester’s appeal is that much stronger.


Obviously, there’s a point where Lester costs too much. Josh Bell and change? Seems acceptable. Josh Bell and Tyler Glasnow? Probably not acceptable. The Pirates can’t get Lester for less than the Red Sox are willing to sell him for, and they’d also have to out-bid their competition. But they can do so much prospect mixing and matching, and the Pirates with Lester might well be the best team in the National League Central. At the moment they’re projected in the NL’s second tier, but add Lester in there and they might fall short only of the Nationals and Dodgers. And again, there’s the factor where not getting Lester could mean a rival gets Lester, which does the opposite of improve the Pirates’ odds.

The Pirates are well positioned to make a big splash. They’re almost a perfect match for Jon Lester, and because of his contract situation, the organization wouldn’t have to mortgage all the future to bring him in. For Neal Huntington this deadline shouldn’t be Jon Lester or bust, but there’s an opportunity here for the Pirates to make their biggest move in decades. It’s a move that would make all kinds of wonderful sense.

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Jeff made Lookout Landing a thing, but he does not still write there about the Mariners. He does write here, sometimes about the Mariners, but usually not.

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