Uh-oh, that’s a red flag: things GMs often say before signing terrible contracts

“This is a guy that has been a big winner. He’s been a performer when it counts the most.”

These are the words of former Boston Red Sox general manager (GM) Ben Cherington, who beamed when the Red Sox signed 2012 World Series Most Valuable Player (MVP) Pablo Sandoval after they lured him away from the San Francisco Giants in free agency. And while Sandoval was indeed a “big winner” — a key part of the Giants’ core for three World Series championships — and had previously been a “performer when it [counted] the most,” he would turn out to be an all-time awful free-agent signing. Just three years into his five-year contract, the Red Sox would release the light-hitting, minimally effective third basemen with $48 million left to be paid on his $95 million contract.

Let’s be clear: Sandoval turned out to be one of the worst free-agent signings in a way not even the most analytical, future-thinking GM could have predicted. But Cherington’s comments in his press conference are a phenomenal example of things GMs say when they have just signed what will turn out to be a terrible contract. 

And with Major League Baseball (MLB) free agency ramping up and several managers ready to sign massive deals — in doing so, likely unknowingly submitting an implicit future letter of resignation à la Cherington — what better time to explore things that GMs say that are often red flags of an impending albatross contract?

Championship pedigree

This is by no means an indictment of ring-winning players, but when a championship pedigree is one of the top reasons a GM cites for inking a contract, it’s not a good sign. This is more a matter of circumstance than any fault of the player. Championship-winning players tend to be older and often on the downswing of their careers when they become free agents or are joining less successful teams where they will be asked to contribute in a bigger role compared to the role in which they performed at a championship caliber. 

None of this is the fault of the player — but a manager immediately citing a winning pedigree as a reason for signing a player is a great indicator that a team is outbidding other teams for the privilege of overpaying an asset that will decline in value or be used in a potentially outsized role. It's never a good sign if that’s one of the most attractive features of a new signee, and often a bad sign for the team’s future outlook.

Grit and toughness

Similar to a championship pedigree, there’s nothing wrong with being gritty and tough. Hunter Pence was a phenomenal example of a gritty player with immense value to his team as a member of many successful San Francisco Giants casts. But when grit and toughness are the number one calling card to an expensive contract rather than offensive prowess or defensive flair, it’s a bad sign. Grit is a better number one calling card for mascots than it is for expensive free-agent signings.

Versatility

This is not a knock on versatility. The Los Angeles Dodgers continue to amaze every year with a lineup flexibility afforded by having loads of quality players capable of playing multiple defensive positions at a high level. But generally in a free-agency climate where it’s hard enough to get a player who plays one position well for a fair price, it is rare to get a free agent who can play multiple positions without overpaying. 

Versatile utility man Marwin González was a valuable player for the Houston Astros during their championship run, but, by hitting .248 with 20 home runs after signing a 2 year, $10.5 million per-year deal, he certainly was not a high-value free-agency acquisition for the Boston Red Sox. Versatility matters, just not as the number one source of value for acquisition.

So in the coming days, as free agents amass many shiny new contracts, we will have the fun of projecting who will be a great signing and who will be a bust. All warnings aside, free agency is still a supremely fun time to be a fan. After all, what’s not to love about being able to add talented players to your favorite team’s roster without having to deal with prospects and assets?

But it’s time we start watching press conferences introducing free agents with a politely futurist, skeptical mindset. Sometimes the writing is on the wall that a team might have inked a Sandoval-esque contract that will hamstring the team in the years to come.