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.

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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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DG Lewis
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DG Lewis

You had me until “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.”

You put Bell’s value at $20M-$30M. The “lower end of Pittsbugh’s organizational top 10” are borderline top-100 prospects (Hanson and McGuire, 6 and 7 per MLB’s top 10, are 80/81 overall), so a reasonable value for a guy in the lower end of Pittsburgh’s top 10 is around $5M.

Lester’s ROS projections on this here website are 1.3 to 1.6 WAR. Let’s use 1.5, and assume that is really an improvement in 1.5 expected wins for the Pirates as Volquez gets bumped to the bullpen and someone like Frieri gets bumped off the 25-man.

So the Pirates are paying $25M-$35M in expected value for 1.5 wins. That’s somewhere between $16.5M and $23M per win.

Taking Nate Silver’s original curve (from 2005, when the average cost of a win was $2M) and scaling it by a factor of 3, the marginal value of a win peaks at around $13.5M. There is NO point on the win curve where $16M+ per win is justified.

Soxfan
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Soxfan

The compensatory pick would likely be worth more than Bell. I don’t do this if I’m Cherrington for a middling prospect like Bell in his age 23 season getting his first taste in AA. I would rather draft an 18 year old with athleticism that might make AA before becoming a grandfather, and with more athleticism and a lower k% to boot. You are right with your math but the marginal improvement Lester brings needs to be greater in return than what Boston gets for just letting Lester walk.

Soxfan
Guest
Soxfan

Sorry age 22 season, still behind the curve.

RetireNutting
Guest

I’d do Bell and Heredia or Tony Sanchez for Lester and Middlebrooks (dreaded change of scenery)

Justin
Guest
Justin

Remember that when the likely comp pick never makes it to AA.

Soxfan
Guest
Soxfan

John Lester has the second most pitcher war in baseball this year behind King Felix. He is an elite player and even for a 2 month rental you need a higher ceiling player than Bell. Look at the Oliver projections for Bell, they are terrible. Better off either resigning Lester (like they should) or letting him walk and drafting a player with serious potential, not acquiring spare parts like Bell.

Justin
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Justin

Why exactly are you looking at Oliver projections made before the season for a guy who was in A-ball last year as your evaluation?

Soxfan
Guest
Soxfan

Because they are the only projections currently available to the public, they run for 5 years, and the player hasn’t made significant statistical changes in this current season.

Justin
Guest
Justin

Moving up a level and improving output in every offensive category? Yeah, that’s nothing. It’s not like the FSL is an offensive league either, he was leading the league in wRC+ when he got promoted.

Soxfan
Guest
Soxfan

He improved his k%, his .iso dropped but remained in range of similar to previous year at lower level, and the increase in woba/obp/ba can all be attributed to his 60 point babip increase as they all increased by fewer than 60 points. Was that babip increase due to better contact? Certainly possible, but he wouldn’t be the first player to see a spike in numbers with inflated babip. As to wrc+ yeah he profiled very well as anyone playing A ball in age 22 season should. Same reason JBJ masqueraded as a competent hitter in lower minors, older players tend to perform well when playing against kids.

Justin
Guest
Justin

You say that like he has no pedigree and is repeating the level, neither of which are true.

.45 pts babip and it’s not like .364 is ridiculous, or he even has a long track record pointing otherwise.

Soxfan
Guest
Soxfan

I never said either. I said he is old for the level (A+) and that his numbers there were similar to another player who dominated A+ at age 22 but can’t hit, Jackie Bradley Jr.

DG Lewis
Guest
DG Lewis

He actually doesn’t turn 22 until August 14, so I believe most would consider this his age 21 season. Which puts him (per BB-Ref) 1.6 years younger than the average age for A+, which is sort of the opposite of “old for his level”.

DG Lewis
Guest
DG Lewis

A comp round pick has an expected value of around $5M, because your 18 year old with athleticism might bust out at high A.

You can prefer the comp pick to Bell – but all the accepted valuations of draft picks and prospects would say that you’re mistaken.

Soxfan
Guest
Soxfan

Most now put that number in 8 figures, the $5 million label is very much in dispute. I just don’t think Bell is worthy of his prospect status given athelticism age at level and projections. He is worth 30m if he really is a top 30 prospect. Projection systems don’t see that, some human evaluators do. Joc Pederson? Done and done. I’d even take a chance on someone like Tavaras. Bell is much more likely to be a 1 tool type with gap power negative defensive values and negative baserunning values. Even with power he only managed a .160 ISO and rode a >.360BABIP as a 21/22 year old at high A ball this season. That is a future role player not a future all star and Boston isn’t Tampa the money value in young players doesn’t hold the same real world value with a payroll ceiling of $200 million.

Roto Wizard
Member
Roto Wizard

@Soxfan Pederson or Tavaras? I think you’re confused on how much value 2 months of Lester really has.

A. Lane
Member
A. Lane

What compensatory pick are you talking about?

Soxfan
Guest
Soxfan

The pick Boston gets for letting him leave after he declines the qualifying offer.

A. Lane
Member
A. Lane

I was under the impression that Boston was attempting to resign him, and a trade may not effect that, thus the QO would be to just suppress his market.

You are certainty entitled to you valuation but Bell lost significant time to a knee injury, was still below the average age for A+. Are you really knocking him because a high BABIP, I thought it was understood the distribution of talent is greater in the minors thus outliers more likely. League average ISO is .112 in the FSL.

I’d pefer Joc Pederson too, but isn’t that asking a little much?

Soxfan
Guest
Soxfan

I’m talking about the Red Sox. They would get the comp pick letting him walk. They have 0 intention to resign him, offered 4/$70, and apparently are hesitant/refusing to go past 4 years. I would rather have the comp pick than Bell. Higher potential ceiling. I’m knocking Bell for producing lesser numbers in age 22 season at A+/AA level than Jackie Bradley Jr, a non prospect(who was also listed way too high given age at levels). Garciaparra, Pedroia, Bogaerts, Betts were all in majors age 21 season. Players who reach the majors as non pitchers at age 24 or later rarely become All Stars, or even above average regulars. The Red Sox intend to compete every year, and Betts’ ceiling is much higher than Bell, so is Rusney Castillo’s, who only costs money. I don’t see the point in acquiring Bell for the Red Sox. As a 1st division team if he isn’t a borderline All Star there is no point in acquiring him. His absolute ceiling seems more like Brandon Moss, which is unlikely given his age and performance, he is more likely a 4th outfielder type. Let Lester walk and take the 2% chance on a superstar from the draft pick instead of the 30% chance at a major league regular someone like Bell represents.

Andrew
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Andrew

I was not aware of that concerning Lester, i thought 4/$70 was Boston’s starting offer. I see your point about upside, though don’t SS/CF prospects have earlier debut ages as a population? And the Jackie Bradley comparison reeks of availability bias. I just consider cavalier to dismiss a 30% 2.0 WAR/600 for admittedly a 2% chance at a 6.0 WAR/600.

King Buzzo's Fro
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King Buzzo's Fro

If the Red Sox want to resign Lester, why are they concerned about the comp pick? Obviously Lester could sign anywhere, but if THEY want him, they could obviously afford him. It will be interesting to see if they hold the line on contract years for him and not end up with Hamels 2.0 situation, letting someone else give him 6-7 years.

Steinbrenners Calzone
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Steinbrenners Calzone

The Pirates will not get a comp pick for Lester. He has not played for the same team all year and they would not make him a qualifying offer. He would just walk.

LukeNalooshe
Member
LukeNalooshe

He’s 21 years old as of today. He crushed in A+ to a 156 wRC+ in ~360 PA’s, and he had a highly impressive 11.8% K% in the process, well below league average.

He’s 21-years old right now in AA. He’s an impressive prospect.

Bell rung?
Guest
Bell rung?

Josh Bell is still 21, and will be 22 in AAA next year. I think your “grandfather’s” clock on prospects is starting to lose the ability to tell time.

Also, Bell is a Top 30 prospect now, so not sure what your definition of “middling” is and, finally, Josh Bell’s K rate this year is 12.6%.

Are you sure you’re participating in the right Comments section? Please advise.

jdbolick
Member
Member

A compensatory pick probably wouldn’t come close to the value of Josh Bell, who was considered one of the top talents in his draft and only fell due to signability, then has shown reasonable progression as a minor leaguer. Bell would have a significantly higher ceiling and a significantly higher chance of becoming some sort of major league contributor than a compensatory pick.

Carlos
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Carlos

You forget to include the value of WAR in the post-season which is the main point of getting Lester, especially that one game in a potential wild card face off.

munchtime
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munchtime

I was about to make this same point. Its a gamble, but if you get into the playoffs… how much is a win in the playoffs worth?

Arc
Guest
Arc

Terrible analysis. The goal is not to win enough games to make the playoffs – or even to make the playoffs by itself. The goal is win the World Series. That is the only value the Pirates see in Lester and it is the value you elect out entirely.

I don’t have a model for the value of postseason wins or the value of a World Series. If you do, you should present it. Even if you don’t, you need to acknowledge it as the single biggest missing variable in the question of his value balanced against e.g. Bell’s. Historically, very smart, better-informed baseball executives have generally valued those things more than prospects like Bell.

Johnston
Guest

Terrible analysis. Winning the WS is a goal. There are many. Making money, increasing attendance, reaching the playoffs, remaining playoff competitive, rebuilding the team – these are also goals.

arc
Guest
arc

Of which a grand total of zero are factored into the original pseudo-analysis.

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