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When will the Yankees regret the Jacoby Ellsbury contract?

Dec 4, 2013, 10:47 AM EDT

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These huge, later-career deals never turn out great. The best you can hope for when you sign a 30-something baseball player to a hugely expensive long-term deal is that he will have a couple of good years on the front end to boost up his value, have a nice rebound year somewhere in the middle, and not be utterly useless and difficult to deal with at the end.

You can go down the list of players signed longterm after the age of 30 – Alex Rodriguez, Albert Pujols, Adrian Gonzalez, Josh Hamilton, Alfonso Soriano, Vernon Wells, Ryan Howard, Jason Giambi, Ken Griffey Jr., Mike Piazza, on and on — and you will find, over and over, deals that teams regretted t some point or other.

So the Yankees will inevitably regret signing Jacoby Ellsbury to a seven-year, $153 million deal — the real question is when. If they don’t regret the deal until 2018 or 2019 — when Ellsbury is a 35-year old coming to the end of his deal, struggling to stay in center field, constantly battling some nagging injuries — then you would have to say that they should feel pretty good about things. The trouble with these deals is that the regret often happens much earlier than you expect. I’m sure the Angels KNEW they were going to regret the Josh Hamilton deal at some point. I just don’t think they expected it to be the first year.

Ellsbury, when healthy, is a fabulous baseball player. I’ve seen him compared pretty often with Carl Crawford, and Crawford was pretty great as a young player. But I think Ellsbury is an even better player than Crawford was in Tampa Bay. For one thing, he plays centerfield while Crawford played left. They were both superior defenders, but a superb center fielder is quite a bit more valuable than a superb left fielder. Ellsbury also gets on base more and might even be a more potent base stealer (last year, Ellsbury stole 52 bases and was caught just four times all year — Crawford led the league in steals annually but would get thrown out a bit more).

Also, Crawford never had a season like Ellsbury’s 2011, when he hit .321/.376/.552 with 32 homers, 105 runs scored, 119 RBIs and 39 stolen bases (though that year he was caught a lot — 15 times).

Then again Crawford was also much more durable than Ellsbury. From 2003 to 2010, Crawford played 140-plus games every year but one, and even in the year he was hampered by injuries he played 109 games. Ellsbury meanwhile has had two of the last four seasons destroyed by injuries — he played just 18 games in 2010, just 74 games in 2012. Nobody can say if those injuries project anything for the future but they are part of his history.

The Yankees have so much money — and so much money on the line — they figure he’s worth the risk. I can see their point. If the Royals or Mariners or Brewers or some team like that had given Jacoby Ellsbury a seven-year, $153 million deal, you could say without any hesitation that they had lost their minds. That’s exactly the sort of deal that can paralyze a smaller franchise for a half-decade.

But the Yankees are a different category. The Yankees in that too-big-to-fail category — they have money on top of money, and they are constantly aware that if they put a losing and uninteresting team on the field, everything crashes. Nobody buys their absurdly high-priced tickets. Fewer people watch their cash cow Yes Network. The back page of the Post and Daily News looks elsewhere. The Yankees brand — the most lucrative in America — starts to devalue a little bit and then a little bit more and … they just can’t let that happen. Money, they have. Wins, they need.

And so the Yankees are playing a different game. If they get even one superstar year and maybe a couple of good years from Ellsbury, they will probably be pretty happy.

How good a bet is Ellsbury to have one more season like he did in 2011? I’m not sure. That was an unusual power surge from a player who has never hit double-digit homers any other year. Then again, that’s a very short porch in right field at New Yankee Stadium.

Truth is, we can spend a lot of time trying to compare Ellsbury to other players — his Baseball Reference comps of Phil Bradley, Tony Gonzalez and Roberto Kelly do not strike an encouraging note — but it’s hard to find many players like Ellsbury in baseball history. He stole 70 bases in a season. He hit 30 home runs in a season. There’s only one other player in baseball history who pulled off those two feats in a career, Eric Davis. And he had a rebirth in his mid-30s, even while battling colon cancer.

My gut instinct is that it will work out for the Yankees. But I say this in part because things always seem to work out for the Yankees.

I can say this with more confidence: If the Mariners sign Robinson Cano … that won’t work out.

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