John Lackey

Revisiting the Red Sox’s 2014 Trade Deadline

On July 26, 2014, the Red Sox lost 3-0 to the Rays. It dropped them to 47-57, 10.5 games behind the Orioles in the American League East. Their season was over and they knew it. Beginning that day and continuing over the next five, the front office would complete six trades that would alter the construction of Boston’s roster for years to come.

Let’s go over those transactions, what the thoughts were behind them (presumably) and how that thinking may have changed 10 months later.

July 26

Trade 1: Jake Peavy and cash to the San Francisco Giants; Received Edwin Escobar and Heath Hembree

Who Boston Gave Up: At the time of the deal Peavy was struggling with a 4.72 ERA. Of course as soon as he got to the Giants he became peak Peavy again, throwing 78 innings of 2.17 ERA ball, but that doesn’t matter to Boston. Good for Peavy, who won his second ring in as many years with the Giants and netted himself a two-year, $23 million deal to stay in San Francisco. He wasn’t needed in Boston anymore.

Who Boston Received: What matters here is that Escobar and Hembree came to Boston for half a season (what was remaining on Peavy’s deal at the time) of an older pitcher who wasn’t pitching well. Escobar, the get in this deal, just turned 23 years old. He’s a lefty with some speed on his fastball, two average off-speed pitches, and the potential to step into the back or, if everything breaks right, middle of a major league rotation sometime in the near future. His upside is about what the Red Sox gave up in Peavy (not the Cy Young Peavy, but the Red Sox version), but with seven years of control at a low cost instead of three months at a high cost. Right now he’s on the disabled list with left shoulder inflammation, which does not sound good, but then that’s the life of a pitcher.

The other player in the deal was Heath Hembree. The scouting report was that he has a fastball that reaches the mid-90s, but not a whole lot else, but he’s doing quite well in Triple-A this season with 12 strikeouts to only two walks in 12.1 innings.

Utterly Arbitrary Grade: It’s unclear how the careers of the two pitchers who came to Boston will play out, but as with all young pitchers, the Red Sox got themselves two lottery cards and, at least in one instance, a card with decent odds of turning into something. Even in light of Peavy’s success with the Giants this deal looks like a steal. A.


July 30

Trade 2: Felix Doubront to the Chicago Cubs; Received a player to be named later ( Marco Hernandez)

I’m going to skip the boilerplate and just say that Marco Hernandez has a .610 OPS in Double-A as a 22-year-old. Further I’m going to say Felix Doubront, after a short required post-Red Sox tour of duty with the Cubs, was released and as of this writing is out of baseball. Generally I don’t like deals where one club deals a major leaguer for a minor league nobody. Even if the major leaguer is not very good, he’s still a major leaguer, but in this case, this is effectively nobody for nobody. Moving on…


July 31

Trade 3: Traded Andrew Miller to the Baltimore Orioles; Received Eduardo Rodriguez

Who Boston Gave Up: At the time of the deal Miller was one of the best relievers in baseball. Now, he’s one of the best relievers in baseball. That’s a tough standard to maintain, though. In 2014, Miller was worth 2.2 fWAR, seventh-best in baseball among relievers. Care to guess who was the seventh best reliever in baseball by the same metric in 2010? Matt Belsile. Sure it would be nice had the Red Sox re-signed Miller, but given who he is and what they got, it’s still a deal you make every time from Boston’s position.

Who Boston Received: Eduardo, or Eddie, Rodriguez, came as a highly touted 21-year-old starter, one of the best prospects in Baltimore’s system. But he wasn’t supposed to be this good. Upon getting to Pawtucket, he altered the way he threw his changeup and took off from there, crushing the International League through the end of the 2014 season. This season he’s picked up mostly where he left off.

Utterly Arbitrary Grade: This is exactly the kind of deal an out-of-contention team should make. Exactly. The fact that the Red Sox netted their best pitching prospect helps the optics of it, but even if Rodriguez blew out his arm tomorrow, a high upside starter for half a season of a reliever, even one as good as Miller, is a no-brainer. Sure it would be nice had the Red Sox re-signed Miller, but given who he is and what they got, it’s still a deal you make every time from Boston’s position. A


Trade 4: Traded Stephen Drew and cash to the New York Yankees; Received Kelly Johnson

Again no boilerplate here. This one was pretty simple, if notable because of the organizations involved. The Red Sox had re-signed Drew to play shortstop on a contender. They were not a contender, thus they didn’t need Drew. The Yankees needed someone to play second base while they chased a Wild Card. Without Drew the Yankees didn’t need Kelly Johnson. The Red Sox, as it turned out, didn’t need him either, flipping him to Baltimore for Jemile Weeks and Ivan De Jesus at the end of August. De Jesus was cut loose and is now in the Reds organization while Weeks is (not hitting) in Pawtucket.

The end result here was the Red Sox didn’t have to pay the last two months of Drew’s contract. Mission accomplished!


Trade 5: Traded John Lackey, Corey Littrell, and cash to the St. Louis Cardinals; Received Allen Craig and Joe Kelly

Who Boston Gave Up: John Lackey had a year and a half of his contract left when Boston sent him to St. Louis. Due to a clause in his contract that specified he would play an additional year at the major league minimum if he missed a year with an arm injury, Lackey was a steal. The Red Sox had Lackey, a number two or three starter, at about $600,000, for a full season. That’s value right there, and the front office should have extracted value in return. They… sort of… did?

Who Boston Received: There was talk of receiving a top prospect but the Red Sox went a different route, opting for major league-ready players in return. They got, as you know, Joe Kelly and Allen Craig.

We’ll start with Craig. Clearly a buy-low attempt by the front office, the former All Star had received MVP votes in two seasons prior to suffering a Lisfranc injury that essentially wrecked his 2014 season. The hope was an offseason of recovery would do wonders and the Red Sox would have an All Star on a long-term, low-cost deal. So far, at least, this has not happened, and it has not happened in a profound way. Craig has been horrendous, batting .130/.235/.192 during his time with Boston. The problem is that if Craig isn’t hitting he doesn’t bring value on defense or on the bases, and he’s not especially great at getting on base either.

The Red Sox sent him to Pawtucket. His career isn’t over. There is still a chance to salvage some value here, but just the fact that I’m using the word “salvage” should make it clear how badly this part of the deal has gone. At this point the Red Sox couldn’t give Craig away, let alone trade him for something valuable like a year of a good starting pitcher.

Then there’s Joe Kelly. Kelly may or may not be a starting pitcher. There’s a case to be made that he’s pitched much better than his ERA shows, he’s young, he’s got a woof’n fastball, and he’s under team control until 2019. Those are all points in his favor. And even if he’s a bullpen arm, he’s got some value. One could make a case that Kelly is worth a season and a half of Lackey. I’m not sure it’s a case I’d make for this team as currently constructed, but you could construct an argument that wouldn’t be nuts.

Utterly Arbitrary Grade: It’s important to note that the Red Sox received nine player seasons for a year and a half of Lackey. Right now they have six plus of those player seasons remaining. The returns aren’t promising, but there is still time. D


Trade 6: Traded Jonny Gomes, Jon Lester and cash to the Oakland Athletics. Received Yoenis Cespedes and 2015 competitive balance round B pick

Who Boston Gave Up: We’ll dispense with Gomes because this isn’t about him in any way at all. The Red Sox season was over and he had no more usefulness left. This is all about Jon Lester, the best pitcher the Red Sox have developed since Roger Clemens. I’m not going to rehash all the contract negotiations here, but in the end the Red Sox determined they couldn’t meet Lester’s price. Then, during the off-season, they attempted to meet Lester’s price, which by that time had gone up. I’m shaking my head right now. I consider myself an objective analyst but it is admittedly difficult to be objective about this. Given where Lester was in his career, you can maybe understand why the Red Sox made the offer they did. But by the time the trade deadline rolled around the team had succeeded in poisoning the well to such an extent that they felt they couldn’t sign Lester. We now know with some certainty that had they come to Lester on that day and offered him the six year, $135 million deal or even a slightly lesser variant of the same deal they would present to him in three months, Lester would still be in Boston.

This would be a whole lot easier to stomach if the Red Sox didn’t need Lester but of the holes on this current team, the biggest is at the front of the starting rotation. Losing Lester means the team better have received something hugely intensely amazing in return…

aaaaaaaaaaaand they didn’t.

Who Boston Received: Yoenis Cespedes was and is a good power-hitting outfielder who the Red Sox might have thought they could sign long term. They couldn’t agree on terms and Cespedes was dealt to Detroit for Rick Porcello, who the team then gave the money they initially offered to Jon Lester to. Porcello should do fine for Boston but unless he develops new strikeout skills, he’s not the pitcher Lester was.

By the letter of the law, the Red Sox turned a half season of Jon Lester into a season and a half of Rick Porcello, plus exclusive negotiation rights that turned into a four-year extension. Yet it’s difficult to look at it that way. Lester wanted to stay in Boston. The Red Sox needed him to stay in Boston. He should still be in Boston. But he isn’t, and it’s hard to look at that as anything other than a huge mistake.

Utterly Arbitrary Grade: I really wanted to give this an F, but Porcello is a good pitcher and an asset, no matter what you think of his contract. C-/D+


The focus on major league players was an attempt to bolster the roster for a playoff run in the short term. Plainly put, that part has not worked. Craig and Kelly are disappointments or non-factors, and it’s not hard to see that the team would be better off with Lackey. Porcello is, again, fine, but he’s a step or two back from Lester. The fact that Craig is now in Triple-A adds an ironic twist to Boston’s insistence on bringing back major league players in these deals, as well as a sad statement on their lack of success. Oddly, the player who may present the largest impact to the major league team might be Eduardo Rodriguez.

Boston’s strategy appeared to be similar to how some teams (most teams?) approach the draft: accumulate as much talent as possible regardless of position and let things sort themselves out later. The Red Sox did that to some extent by acquiring Cespedes and then flipping him to Detroit for Porcello. Beyond that, Boston may have under-estimated their ability to upgrade the offense through free agency during the then coming off-season. If they knew adding Pablo Sandoval and Hanley Ramirez were possibilities it makes you wonder why they’d want Allen Craig.

The story of the 2014 deadline deals isn’t over. We won’t know for a long time how this whole thing plays out. But right now, 10 months after the fact, with holes throughout the rotation and an overabundance of money if not talent committed to the outfield, it’s difficult to call those six days successful.

Top photo by Bob DeChiara/USA Today Sports Images

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2 comments on “Revisiting the Red Sox’s 2014 Trade Deadline”


I’m not a big fan of the analysis of the Lester trade. It certainly was no smashing success, but as it stands the Red Sox traded two months of Lester for two months of Cespedes and a year of Porcello, plus the ability to sign Porcello to what could end up being a solid contract for an unusually young veteran pitcher.

We need to stop distorting the narrative regarding Lester. The best example is how some people outright lie by saying Boston “lowballed” Lester with its initial offseason extension offer, which is patently not true if you look at where he was and what the status of contracts were at the time. It’s likely nobody anticipated the level to which pitching contracts exploded over the past 400 days, and its only with the hindsight of seeing Lester return to peak dominant form that anyone can say he should have been paid more. Hindsight regarding a contract that could have been given to a veteran is a poor way to evaluate a trade. It should be judged by what was given up and what was brought back; the rest is just noise.

The Lackey trade is a clear different story. Boston’s major issue has been getting steady competitive starts from the rotation, the exact thing Lackey would have offered, and all for peanuts. Kelly has actually greatly exceeded my expectations, but Craig has both underperformed and been a very unneeded part. Your grade and evaluation is right on there.

Never realized how many people think they are qualified as major league baseball general managers. LMAO!

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