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Come Fan with UsSunday, June 21, 2026

The lessons the Red Sox can learn from the Pablo Sandoval disaster

The Red Sox thought they were getting a 28-year-old hitter in his prime. It, uh, didn’t work out.

MLB: Boston Red Sox at Philadelphia Phillies
MLB: Boston Red Sox at Philadelphia Phillies
Eric Hartline-USA TODAY Sports

On Nov. 25, 2014, the Red Sox signed a 27-year-old third baseman to a five-year contract. That player was a career .294/.346/.465 hitter, which is a pretty big deal for someone who spent half of his time at AT&T Park. He was a (deserved!) Gold Glove finalist and a switch hitter, and his swing was absolutely built for Fenway Park, like few hitters before him.

Pablo Sandoval ended up as one of the worst players in Red Sox history. If you use dollars-per-WAR, it’s not even close. Even Carl Crawford looks at the Pablo Sandoval deal and winces.

Our job, then, is to reconstruct what went wrong. What lessons have we all learned from this deal, and how can teams like the Red Sox avoid these mistakes in the future?

Lesson #1: Don’t sign players to a long-term deal unless they have abs of steel

Yes, and ... wait, what? That’s ludicrous.

Tony Gwynn

I don’t know when that picture was taken, and I don’t care. Tony Gwynn used to have the lithe body of a college basketball player, and then he didn’t. At no point did he stop hitting baseballs hard. He was a marvel, an absolute marvel, and nobody cared what he looked like.

I’m not sure if there’s a great example in recent Red Sox history of a hitter who might have been a little round above the belt but still performed at an All-Star level until he was 40. If I think of one, I’ll let you know.

This isn’t to suggest that Sandoval was remotely comparable to Gwynn or David Ortiz. Just that the argument “Hitters need to have abs of steel to hit” is patently false. If you didn’t like Sandoval’s chances to succeed, you would have to offer up reasons other than “not muscly,” because hitters need to have muscles until they don’t. If your argument is that Sandoval was specifically ill-equipped to carry that much extra weight — I would listen to the evidence for that argument! — that’s one thing. But the blanket statement doesn’t teach us anything.

Lesson #1: Sandoval wasn’t that good to begin with

The first ... oh, come on. This isn’t it, either.

Sandoval wasn’t coming off his strongest season in 2014; that much I’ll concede. But he still had a 111 OPS+ and 16 homers in one of the most extreme pitcher’s parks in history. His above-average defense (I watched it, it was real, I promise!) made him a three-win player that year, and he was just 27. That’s a player who shouldn’t scare a team away from a five-year deal.

Keith Law is a smart feller, and he came to a similar conclusion:

He’s too young to see a sudden loss of skill, like a drop in bat speed, and despite his body, he moves fairly well over at third base.

At the time, I couldn’t have agreed more.

There are 174 players in baseball history who had six or more seasons with an above-average adjusted OPS before turning 28. It is, for the most part, an impressive list of names and complete careers. There’s Jim Rice, Gary Carter, George Brett, Reggie Jackson, Rod Carew ... and those are just the players with six, like Sandoval. Of course, Sandoval wasn’t hitting at a Hall of Fame level, so it’s probably more sensible to put him with players like Carlos May, Al Oliver, Buddy Bell, and Carney Lansford.

Of those 174 players, only 12 of them failed to have a single above-average offensive season after turning 27. Except five of them haven’t turned 27 yet, so Mike Trout, Bryce Harper, Giancarlo Stanton, Freddie Freeman, and Anthony Rizzo are off the hook.

That leaves us with ...

  • Braggo Roth
  • Cecil Travis
  • Freddie Lindstrom
  • Gregg Jefferies
  • Kal Daniels
  • Red Murray

Roth had injury problems, and his big mouth (dude’s nickname was “Braggo”) kept teams away from him when he was released. Travis was never the same after World War II. Lindstrom and Daniels both had knee problems.

Jefferies and Murray each had their own maladies, and they drifted away, but neither of them were nearly as awful as Sandoval was with the Red Sox.

Which means that in baseball history, there hasn’t been a collapse like this that wasn’t directly attributable to injuries. When a player is solid-to-excellent multiple times in his early 20s, he almost always gives his team some value after turning 28.

Sandoval wasn’t an MVP candidate, and he wasn’t on a Hall of Fame path, but he was a two-time All-Star with a history of hitting better than his peers. That didn’t mean there wasn’t a chance for a disappointing contract, but it did mean that a complete and utter collapse into the bowels of the nightmare void was nearly impossible.

It happened. But the lesson isn’t that Sandoval wasn’t that good to begin with. He was fine. Better than fine. And his swing really was made for Fenway.

Lesson #1: Free agents will break your heart

Bingo.

They’re the biggest scam in baseball, really, other than pre-arbitration salaries and what minor leaguers make. Paying baseball players to get older is always a bad idea. Time will come for them all, even Mike Trout, and yet teams have to pay them as if that’s not true because it’s just about the only way to build a competitive team.

With every free agent, you can look at the projected stats and extrapolate what the player might do over the life of the contract. You can factor in the decline and make an educated decision.

And once you’ve done that, the free agent can join the team and throw those stats and projections into a vat of acid. This is the only lesson Sandoval can really teach us: Sometimes, things just go all screwy.

Boy, did things go all screwy with Pablo Sandoval and the Boston Red Sox. A change of scenery is going to be welcome, I’m sure, and he’s not finished yet. Someone will be glad to pick up a player with Sandoval’s history on a league-minimum salary. The odds are against him, though, and it’s likely he’ll never be an even average hitter again.

It was a mess. It will continue to be a mess. But there’s only one lesson to learn, and it’s not a very helpful one. Sometimes, things just go all screwy.

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