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When will the Yankees regret the Jacoby Ellsbury contract?

Dec 4, 2013, 10:47 AM EDT

ellsbury Getty Images

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.

103 Comments (Feed for Comments)
  1. realitypolice - Dec 4, 2013 at 10:43 PM

    The question is not “when” but “if”. People who assume that it is inevitable that the Yankees will eventually regret this contract don’t understand their mindset. If Ellsbury winds up being a main cog in two World Series winning teams in the next 4 years, then the Yankees will never regret the deal no matter what he does in years 5,6, and 7. The Yankees don’t wallow in year to year saber metrics. They focus on titles. If there are no titles in the Ellsbury era, they will regret the contract. If there are, then they couldn’t care less if they pay him 20 million dollars seven years from now to shake hands with season ticket holders at birthday parties.

    • timberwolvesbrisin - Dec 5, 2013 at 10:43 AM

      Ummmm, a guy who has only played in 40% of the games in the last four years, who has no power. Its not “if” but “when” he goes on the DL. Sorry 300 hitters with no power are not hard to find, This is a horrible contract.

      You must be a yankess homer…

      • sabathiawouldbegoodattheeighthtoo - Dec 5, 2013 at 4:34 PM

        The contract is for too much money, but that does not make it a horrible contract unless it prevents the team from signing other players. Again, one could argue that not even ARod’s contract is truly horrible for the Yankees. It has not prevented them from dropping crazy money in 2009 and again this season.

        Also, there are few players with upside as high as Ellsbury. Sure, he has had trouble meeting his potential every year, but I prefer to see the team take chances on potentially elite players than stick with dependably average players.

      • basedrum777 - Dec 6, 2013 at 5:50 PM

        Twice players landed on him sliding into a base, once he fouled a ball off of his foot and he collided with another outfielder. When did that start to constitute injury prone? You think that’s expected to continue to happen?

    • redsoxruleskankssuck - Dec 6, 2013 at 9:26 AM

      Hey realitypolicer, try a dose of it!
      2 WS in 4 years??
      Stop smoking cracker-jack, and drinking heaving in the mornings!
      Of you watch the World Champion RED SOX this past fall, you would know that its all about pitching- and skanks have NONE!!!!
      WhoooooooHoooooooo!!!!!
      Lokking forward to the Skank house-of-cards tumbling in on itself once again!!!
      GO RED SOX!!!!!!!!!!!!!!!!!!!!!!
      In only their first year of rebuilding and already a Dynasty!!
      (yankees SUCK!)

  2. voidhelix - Dec 4, 2013 at 11:53 PM

    I`m pretty sure Vernon Wells was 29 when he signed the 7 year contract extension with Toronto.

  3. pastabelly - Dec 5, 2013 at 8:14 AM

    “If Ellsbury winds up being a main cog in two World Series winning teams in the next 4 years, then the Yankees will never regret the deal no matter what he does in years 5,6, and 7.”

    The Yankees have positioned themselves to challenge for a playoff spot, but not contend for WS. Their pitching just doesn’t match up. To get where they need to be, they should focus on 2015 and hope that both Lester and Scherzer get to free agency and sign them both. Perhaps the Red Sox, in letting Ellsbury go, are more mindful of affording the 6/150 that Lester will cost them. It’s fair to say it was also a motivating factor for the Tigers in letting Fielder go. I suppose the Yankees could sign Price, if he’s available, but that won’t hurt Boston or Detroit. Ellsbury is a nice complimentary piece, but he’s not a “main cog”.

    • sabathiawouldbegoodattheeighthtoo - Dec 5, 2013 at 4:28 PM

      I don’t think the Yankees are going to stand pat with their pitching. If CC rebounds, Kuroda resigns and they land Tanaka (not entirely unlikely scenarios) they have a pretty good shot in October.

  4. anotheryx - Dec 5, 2013 at 12:45 PM

    Whenever Ellsbury has a significant injury… which could be next year or never. He is a beast when healthy.

  5. popi1956 - Dec 6, 2013 at 12:38 PM

    Are the redsox part of the Yankee far system

  6. hooterdawg - Dec 7, 2013 at 3:17 PM

    It’s not just that Ellsbury is frequently injured. He also had a reputation for being unwilling to play when he wasn’t 100%. A couple of years ago, there were rumors around the Red Sox that Ellsbury was ‘ milking’ his injuries to stay out of the lineup. Fans were annoyed, and the FO had no comment on the situation. He was never a clubhouse leader – the other players questioned his grit.

  7. spc7ray - Dec 7, 2013 at 6:58 PM

    I don’t like the Yankees—Im a Dodger-But they did well-Basically trading McCann-Ellsbury and Beltran for Cano–That’s a good trade

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