How the Red Sox GM went from the World Series to unemployment in under 2 seasons

The Red Sox won the World Series 674 days ago. Then-GM Ben Cherington couldn’t claim credit for every championship piece, but he could take more credit than anyone else in a suit. He was the toast of Boston. To Ben Cherington!, they toasted, excited about the future, enamored of the present. Then, 673 days later, he was pushed out in favor of an executive who hasn’t won the World Series since Nomar Garciaparra was a rookie.

How did this happen? Transaction by transaction, we aim to find out.

October 31, 2013 - The Day After

Lots of transactions, here, so they’ll have to be lumped together:

MLB transactions, 10/31/13

Daniel Nava - turned into a pumpkin
Mike Carp - turned into a pumpkin

Cherington built a Swiss Army outfield with moving, platoonable parts, and it’s a big reason for the success of the ‘13 Red Sox. Then, after the last drop of champagne hit the ground, they were both ushered away by their fairy godmothers, never to return to that level of production again.

Wait, why the cliché, “Turned into a pumpkin”? Doesn’t that mean they were a chariot when they were temporarily excellent? Chariots would be awful at baseball. They don’t even have thumbs. It makes more sense to say, “Turned into a mouse” or, “Turned into an ordinary stepsister.”

Regardless, the Red Sox got more out of the Nava/Carp tandem than they should have ever hoped to. There really wasn’t anything you would have done differently with those two players. It was easy to be skeptical, but that’s different than actively spending money/time/resources to find an upgrade on two players who were absolutely excellent the season before.

October 31, 2013 - Free agency

Stephen Drew granted free agency
Jacoby Ellsbury granted free agency
Jarrod Saltalamacchia granted free agency

None of these players would have saved the ‘15 Red Sox. None of them would have come close. Jacoby Ellsbury was a taco-granting gift from the heavens, and he was responsible for so much Red Sox mirth. He’s 31 with a league-average OPS, declining defensive numbers, and $111 million left on his contract. He isn’t the player the Red Sox needed this season. He’s not the player they’ll need in the future.

December 4, 2013 - Signed A.J. Pierzynski

It’s easy to make too much about chemistry and clubhouse camaraderie, but it’s also easy to make too little of it. Do you know how much strain Pierzynski puts on the equipment managers alone? They have to custom-order catcher’s masks that can fit over a face shaped like a butt, and when they arrive they find out that the butt for a face is an even bigger butt for a face than they had anticipated, so they have to send the order back and wait for new masks that can fit over a face shaped like a butt. It’s very, very stressful.

Also, Pierzynski was a 37-year-old average-dependent catcher with a spotty defensive record. The Red Sox were hoping he could do what he’s doing right now with the Braves, but it was still a risk. Still, catchers are hard to find, and the Red Sox needed to bridge the gap until Blake Swihart was ready. Giving a multi-year deal to Saltalamacchia wasn’t the way to do that.

December 12, 2013 - Re-signed Mike Napoli

If you’ll remember, the original deal before the season was for three years, $39 million, but a post-contract physical revealed a degenerative hip condition. The new deal was for $5 million guaranteed, with all sorts of escalators and doodads that pushed the salary up with good health.

The risk payed off brilliantly. After the ‘13 season, the team essentially gave him a make-good contract that ended up being the same as the original 3/$39 million deal. Considering that the Red Sox got one more fantastic season and one lost season, and they did it without messing up the long-term payroll, it’s hard to ding this one too severely. When you have a chance to sign an important slugger to a short-term deal, you kind of have to take it.

January 24, 2014 - Signed Grady Sizemore

/squints

Wait, was that really the offseason? There were minor moves for Edward Mujica and John Ely that weren’t included here, but ... really? The reinforcements were Pierzynski and Sizemore?

That’s the offseason of someone who’s a little too confident with the major league roster. That written, it’s not like he had a reason not to be confident. They just won the World Series. They didn’t have a lot of obvious holes. If there were concerns, they had to do with David Ortiz getting old and other players getting hurt, but it’s not like the solution to that was to let Ortiz walk and pick up John Jaha as a free agent.

You can understand how it was tempting, if not logical, to stand pat, mostly.

You can also understand how Dave Dombrowski would have been a lot more active.

May 21, 2014 - Re-signed Stephen Drew

What a weird case. Drew expected a huge contract. Scott Boras promised him one, and why wouldn’t he believe him? He got one for him after college. The combination of spending millions and losing a draft pick was too much for most teams, though, so Drew slinked back to the Red Sox on a one-year deal in the middle of the season. He didn’t stand up after signing the contract, pick his talent up by its underwear, and toss it out an open window, but he might as well have.

Drew was never consistent, but he wasn’t likely to be one of the worst players in baseball, either. When the Red Sox signed him, they were 20-25 and four games back. It made sense to add depth for the comeback that wasn’t to be.

July 26, 2014 - Traded Jake Peavy for Heath Hembree, Edwin Escobar

Like Ellsbury leaving, it’s not like Peavy was going to fix anything. If anything, the Red Sox did well to get two prospects for an average pitcher who was a pending free agent. Just don’t look up what Escobar is doing in the minors right now.

July 31, 2014 - Traded Andrew Miller for Eduardo Rodriguez

Miller has been worth 1.5 WAR, according to Baseball-Reference.com. Rodriguez has been worth 1.3. That’s not how you evaluate a trade like that, especially when one player is a reliever and the other is a starter, but it gives you a hint of how the trade is looking right now. Rodriguez should be good and cheap for a long time. This is one of the strongest trades of Cherington’s career.

July 31, 2014 - Traded John Lackey for Joe Kelly, Allen Craig

Lackey’s value was that he was a proven workhorse who was going to make the major league minimum because of a creative, post-surgery contract. The Red Sox needed players to reload, not rebuild. So here’s where the unconventional trading deadline really started getting weird.

Kelly was never a good bet to stick as a starter, but he was a quality arm under team control for years. Craig was a calculated risk, an All-Star the previous season on an affordable long-term deal. It made sense to me, but I’m just a know-nothing writer. The Red Sox were supposed to get 10 years of production in exchange for one year of solid starting pitching.

Here’s where you start getting into the real reason that Cherington is an ex-GM, though. Do you know why the Cardinals traded Kelly and Craig? Because someone smart said, “I don’t think Kelly’s ever going to start. And I don’t think this slump is temporary for Craig. He’s lost something.” I don’t know if it was a scout, a scouting director, an assistant GM, Skeeter Barnes, or John Mozeliak, or a combination of different voices, but the message came through. These guys aren’t building blocks. There are red flags. Trade them if a better player comes back in the deal.

The Red Sox didn’t have that person. Or those people. Part of that is that the Cardinals were more familiar with their own players. Another part of that was that someone or someones missed the red flags. The GM is the one who pays if everything catches fire.

July 31, 2014 - Traded Jon Lester, Jonny Gomes for Yoenis Cespedes, comp. balance pick

So that’s three deadline deals for a disappointing team hoping to rebound. One was a traditional prospect-for-established player move. Two were less conventional established-for-established moves, with the Red Sox hoping to pick up immediate returns in the short and long term.

The only one who looks good so far: the traditional prospect grab. It’s what’s helping them both now and in the future, like rain on your wedding day. It’s not unfair to wonder which prospects were dangled in front of Red Sox, and if they would have been improvements on Kelly, Craig and Cespedes for 2015, much less the future.

August 23, 2014 - Signed Rusney Castillo

This gets an incomplete grade, as Castillo is coming along, if a little slowly. I’ll bet a few minutes after signing Castillo, though, Cherington squinted at Cespedes really hard for about an hour.

November 25, 2014 - Oh no, don’t go in the closet no no noooooo

Signed Pablo Sandoval as a free agent
Signed Hanley Ramirez as a free agent

Uhrrrrgghhh. Well, let’s dive in. This is Ben Cherington’s Waterloo.

Because of recency bias, people remember Sandoval as the hitter who pounded three homers against the Tigers in the 2012 World Series, or the clutch hitter who helped the Giants get through the 2014 postseason. Before that, though, there was 2010, when the Giants were absolutely desperate for him to anchor their lineup. He lost his job before the end of the season. He was swinging at everything, playing a miserable defense, taking shots for his weight ... sound familiar? He’s always had the potential to disappear for a season.

He’s also still young, and there were also reasons to think he would thrive in Fenway. There are reasons to think he’ll still thrive. But it’ll be too late for Cherington, who knew that there were going to be risks associated with paying a 32-year-old Sandoval millions and millions of dollars, but took that risk to get the immediate production. The immediate production was, uh, damaged in the move.

Far more egregious and harder to explain, though, is Ramirez, who didn’t play a position the Red Sox needed to fill. The only thing Ramirez damaged more than Cherington’s career was the belief that anyone can play left field. Ramirez is literally playing the same position as an older, confused, bulky Manny Ramirez and looking five times worse. The get-the-hitter-first, figure-position-out-second strategy is dead. Cherington killed it. Hanley Ramirez helped bury the body, then kicked Cherington into the hole after it.

December 11, 2014 - Signed Justin Masterson as a free agent

New rule: If the Cardinals aren’t interested in keeping someone, be very skeptical of that someone. This rule doesn’t apply to the Braves, for whatever reason.

December 11, 2014 - Traded Yoenis Cespedes for Rick Porcello

That’s not a bad trick, turning two months of Jon Lester into a year of Porcello. Just make sure not to do anything rash, ha ha, like assume that Porcello’s first excellent season in five tries means that he’s going to be a top-o’-the-rotation mainstay for years. Take a test drive! Don’t do anything rash!

December 12, 2014 - Traded Rubby De La Rosa, Allen Webster for Wade Miley

Miley is doing roughly as well as he did last year. The Red Sox got him to eat innings and be generally competent, and that’s what he’s been.

This was a transaction to help build rotation depth, sure, but it’s also the ghost of a hundred transactions that weren’t made. This was the Red Sox announcing that they were going to build a contender through the lineup, and that they didn’t need anything more than the Mastersons, Porcellos, and Mileys of the world. They were OK winning 6-4, at least until the farm started spitting out better pitchers.

The problem is that the limited ceilings of the individual parts of the rotation meant there was no margin for error. If you take five average pitchers before any baseball season, assume that one will break and one will stink. It’s like a baseball truism. When that happens, you’d better have a backup plan. The Red Sox had prospects, but prospects will steal your car keys and drive into a lake. Relying on average-or-slightly better pitchers also puts a lot of pressure on a lineup. Everyone had better hit like they’re supposed to, or else ...

There are moves that came after this, including a Yoan Moncada deal that Dombrowski is really, really going to enjoy in a couple years, but Cherington is already a dead GM walking by this point. He’s done, even if he doesn’t know it yet. All of this cataloging makes it clear what cost him his job:

1. Too much trust in current players on the roster
2. Too much trust in prospects to hit/pitch immediately without hiccups
3. Too much trust in quantity over quality, especially in the rotation
4. Too much trust in players doing just as well as they did last year
5. Too much trust
6. A touch of downright poopy luck

What would you have done differently? With the benefit of hindsight, everything. Without the benefit of hindsight, maybe traded prospects away for a real ace? Maybe you would have steered clear of Sandoval and/or Ramirez. Maybe all of the above.

That up there, though, is how to go from a parade to unemployment in 674 days. For two straight seasons, the Red Sox weren’t as good as they were supposed to be, befouling their plans to reload instead of rebuild. If they’re good again, keep a thought for Cherington, who was neck-deep in this mess, but who will also be partially responsible for whatever happy fun times might follow.

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