Robinson Cano contract negotiations stalling (but still inevitable)

Rick Osentoski-USA TODAY Sports

The Yankees are supposed to be fiscally sound these days, which would seem to prevent them from signing Robinson Cano to a ludicrous extension. Don't be so sure, though ...

Robinson Cano will be a free agent after this season, and he's talking with the Yankees about an extension. But they're not talking talking. They're apparently pretty far apart:

Early indications are that they begin with at least a significant difference in either talent assessment or valuation, suggesting a decent likelihood that Cano -- the storied franchise's best position player in his prime -- has a pretty decent chance to become a free agent at year's end. While the sides won't admit he's sure to hit free agency, at the very least it's clear there's plenty of work to do.

Here is a (mostly) complete and thorough history of homegrown Yankees leaving via free agency:

  • On December 4, 1990, Dave Righetti signed with the San Francisco Giants.
  • On December 16, 2003, Andy Pettitte signed with the Houston Astros.

This has been the (mostly) complete and thorough history of homegrown Yankees leaving via free agency.

When Pettitte signed with the Astros, there was something of a firestorm. From the New York Times:

While Steinbrenner has pursued other players this off-season, he was strangely indifferent toward Pettitte, who signed a three-year deal with the Houston Astros on Thursday.

''It's a sad deal because the Yankees of the mid-to-late 90's acted the right way and worried about winning,'' the former Yankees official said

Pettitte wanted to go home to Houston, and he is the only homegrown fan-favorite to leave the Yankees as a free agent in the last 25 years. It would have been something of a stretch to call him a star in 2003. He was 21-8, sure, but his ERA was 4.02 (111 ERA+) -- both were right in line with his career marks -- which made him more like Wandy Rodriguez with run support. But he was certainly a part of Yankees lore by that point.

The other homegrown stars and semi-stars -- Derek Jeter, Jorge Posada, Bernie Williams, Mariano Rivera -- were always extended and re-extended, paid handsomely to return to the team that developed them. Those contracts didn't get a ton of press because they were expected from the moment the old contract began. Did you even know that Rivera was a free agent this winter? In an age where reporters feel compelled to tweet rumors based on conversations with mascots, there wasn't a single rumor tying Rivera to another team. Of course there wasn't.

Cano, then, might be the end of an era. He's most certainly a star -- one of the 10 best players in the game. And it's not fait accompli that the Yankees will re-sign him. If the Yankees are interested in winning for the short term, they'll certainly make a run at it. If the Yankees are interested in preserving their legacy of keeping their stars close and other teams' stars closer, they'll make a successful run at it.

But if the Yankees looking to be a rational team making rational business decisions -- apparently the new plan -- they're going to have to think about this one for a bit. Cano is represented by Scott Boras, you know.

In Los Angeles, the cash-rich Dodgers loom as an obvious landing spot. Cano could easily garner a contract worth upwards of $200 million, according to one league official, who requested anonymity in order to speak freely about the situation. His value to the Yankees was almost immeasurable. "He can’t be replaced," the executive said.

A 30-year-old second baseman asking for $200 million fits in well as a replacement for the punchline of this Far Side cartoon. That sort of thing didn't used to matter. The Yankees were adamant about A-Rod breaking the all-time homer record in their uniform, so they didn't care about the red flags associated with signing a player over 30 to a 10-year deal. They care now. And if a team is looking to be prudent, they stay away from second basemen over 30.

It follows that Cano could be the first Yankees star to leave as a free agent since Pettitte. And considering that Pettitte wasn't really a star, this might be one of the only times over the last century that a star Yankee left for another team before the Yankees were through with him. In the days of the reserve clause, it's not like Mickey Mantle or Whitey Ford had much of a choice. There's a century-long expectation built up surrounding the Yankees' ability to keep their players.

Before you write the eulogy of Cano the Yankee, though, consider this: He's the last big contract decision left. The Yankees will pay Mark Teixeira, CC Sabathia, and A-Rod for a while, but they aren't that overextended for a team that wants to avoid the payroll tax. The Yankees will still have over $100 million to spend each season for the next three years, after which they'll have much more.

Pinstriped Bible: Projecting Cano's next 10 years

And behind Cano in the Yankee-legacy sweepstakes we have, who, Brett Gardner? Phil Hughes? Curtis Granderson might get paid, but not if the cost is losing Cano. There aren't any young Yankees who will hit the free-agent market with a lot of force. This is the last monster deal the Yankees will need to give out for a while.

Which means they'll do it. If all this stuff about "Yankees staying Yankees" seems like hokum, I assure you, it isn't. This sort of thing is important to the franchise. There's something to be said about the appearance of invulnerability from a public-relations perspective. If Cano left, the Yankees would look vulnerable. It wouldn't be the kind of thing that brings a civilization down on its own, but it certainly wouldn't help the calculated mystique of the Yankees.

More than that, the Yankees are built to win in the short term. Unless the team -- or Cano -- completely collapses, they'll be a team looking to win now. The combination of legacy and win-now makes it exceedingly unlikely that the Yankees will pass. Boras knows that. And he can wait.

The Yankees aren't going to give a lot of $200 million contracts away in the future. But they still have just one more in them, I'd wager. Cano isn't going anywhere.

Log In Sign Up

Log In Sign Up

Please choose a new SB Nation username and password

As part of the new SB Nation launch, prior users will need to choose a permanent username, along with a new password.

Your username will be used to login to SB Nation going forward.

I already have a Vox Media account!

Verify Vox Media account

Please login to your Vox Media account. This account will be linked to your previously existing Eater account.

Please choose a new SB Nation username and password

As part of the new SB Nation launch, prior MT authors will need to choose a new username and password.

Your username will be used to login to SB Nation going forward.

Forgot password?

We'll email you a reset link.

If you signed up using a 3rd party account like Facebook or Twitter, please login with it instead.

Forgot password?

Try another email?

Almost done,

By becoming a registered user, you are also agreeing to our Terms and confirming that you have read our Privacy Policy.


You must be a member of to participate.

We have our own Community Guidelines at You should read them.


You must be a member of to participate.

We have our own Community Guidelines at You should read them.




Choose an available username to complete sign up.

In order to provide our users with a better overall experience, we ask for more information from Facebook when using it to login so that we can learn more about our audience and provide you with the best possible experience. We do not store specific user data and the sharing of it is not required to login with Facebook.