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Red Sox’s hopes for Jacoby Ellsbury extension getting more expensive with every homer

Jul 21, 2011, 11:51 AM EDT

Boston Red Sox' Ellsbury hits a home run against the Detroti Tigers during the fourth inning of their MLB spring training baseball game in Lakeland, Florida

During a radio interview this morning general manager Theo Epstein noted that the Red Sox unsuccessfully tried to work out a long-term contract extension with Jacoby Ellsbury in the past and would still like to do so, but the center fielder’s price tag is rising rapidly.

Here’s what Epstein said on the Dennis and Callahan Show:

This isn’t the right forum to talk about it. Those conversations are always behind closed doors. But I guess it’s not a secret we sat down and tried in the past to do that, lock Jacoby up, and I hope we’ll sit down in the future again and try to do it once more at the appropriate time. He’s somebody we’ve long believed in, we’ve long seen as a core young member of the organization that we would love to keep around.

Ellsbury is earning $2.4 million in his first season of arbitration eligibility and will be under team control in 2012 and 2013, so there’s no rush to get something done. On the other hand, he’s bounced back from an injury wrecked 2010 to hit .316 with 15 homers in 95 games after totaling 20 homers in his first 349 games, which along with having Scott Boras as an agent guarantees Ellsbury will be looking to break the bank.

Plus, as Rob Bradford of points out Boras has typically tried to avoid letting his clients give up free agent years as part of contract extensions, so even if the Red Sox are willing to meet his rising asking price that may not even be an option. Quite a bit different than just a year ago, when Ellsbury hit .192 and was limited to 18 games by injuries.

  1. proudlycanadian - Jul 21, 2011 at 12:10 PM

    A very risky strategy by Boras and Ellsbury. Given the way he plays, I would expect that he will be injured again before he can maximise his value.

    • adowding3 - Jul 21, 2011 at 5:24 PM

      The injuries from last season were the result of a meet-and-greet with adrian beltre’s knee. He has missed time with some minor tweaks, but aside from your average wear and tear, i feel that the he has been pretty consistent.

      I remember before last year he put on a ton of muscle, ready up his power numbers. This is has been a long time coming.

      PS – I wouldn’t be surprised if some of this success also comes from peace of mind being slotted back in CF. (He never would have collided with Beltre had the Sox not tried the horrendous Mike Cameron experiment)

  2. Ari Collins - Jul 21, 2011 at 12:22 PM

    The Sox would probably go for something like 4 years at $12M per, with a $15M team option and a $3M buyout. Maybe the option vests with PAs. I don’t think the Sox want to be signing him into his mid-30s, though, and they’ve got him until he’s 29 right now at a cheap price, so they have no urgent need to overpay.

    • Chris Fiorentino - Jul 21, 2011 at 12:32 PM

      I agree with this, but there’s no way Bor-ass is going to advise Ellsbury to give up 2 years of FA for the security of only $51 million over 4 years. That would not be logical to a person of Bor-ass’s integrity.

  3. riverace19 - Jul 21, 2011 at 12:51 PM

    The only reason Ellsbury got hurt last year is because he was playing a new position, LF, and wasn’t familiar with the territory… Now that things are fixed, he is allowed to be the player that he is (awesome).
    He showed a lot of pop in spring and I predicted 18 HR… boy was I wrong!
    Ellsbury is a big part of the reason the Sox are in first. After a slow start, he is shooting lasers all over the field, and is becoming a true 5-tool player.
    The Sox can afford him. No doubt.

    • spindervish - Jul 21, 2011 at 1:12 PM

      He’ll never be a 5-tool player. No arm.

      • 18thstreet - Jul 21, 2011 at 2:14 PM

        The 5th tool is his dashing good looks.

      • Chris Fiorentino - Jul 21, 2011 at 2:21 PM


  4. uyf1950 - Jul 21, 2011 at 1:21 PM

    My question/comment is a simple one. Why would Boras and Ellsbury settle for anything in the neighborhood of 4 years/$50M plus or minus. Ellsbury only has to look to his right when he is in the field to see a player the Sox signed to 7 years for $142M. I realize I’m no rocket scientist but where the equity in 2 comparisons.
    Minimally, in my opinion Ellsbury should be looking for and expecting something more then what Jason Bay got from the Mets (4 years $66M) and something probably slightly less then what Werth signed for from the Nationals (7 years $126M). Because if the Sox don’t sign him long term and he continues to play the way he has of late someone else will when he hits free agency. That’s just my opinion.

    • spindervish - Jul 21, 2011 at 1:38 PM

      The fact that he’s not a free agent yet matters. No matter how awesome he’s playing, it’s not reasonable for him to expect fair value FA-type dollars the next two years. At least that’s my understanding of how these things work.

      So, take for example that 4-year, $48 mil figure (setting aside the suggested buyout for now). I’m just making shit up, but let’s say he continues to be awesome the next two years and would have gotten raises to $5 mil and $7 mil in 2012 and 2013 through arbitration. That would mean the proposed deal would in essence be paying him $36 mil for his first two years of FA, which is an AAV that’s pretty competitive with Bay and Werth, to use your examples. This makes the proposal seem a lot more fair than you’re giving it credit for being.

      I make no claims to being an expert on arbitration or FA contracts and the issue of whether Boras would have any interest in such a proposal is a separate and legitimate one, but this seems to me a decent general explanation of why Ellsbury should have no realistic designs on a $100 mil contract right now despite his excellent performance.

      • Chris Fiorentino - Jul 21, 2011 at 2:14 PM

        What he said. In addition, he is guaranteed to be set for life 2 years in advance of free agency. Because right now, if he blows out his knee tomorrow and never plays another game, he isn’t set for life. However, when he signs a contract for 4 years and $51 million guaranteed, his life is set forever. As is the life of his kids. And maybe even his grandkids if he invests it well. Sure, he could take a chance and set up the next 6 generations. But why risk it? And the best part? If he stays healthy and earns the cash, then in 4 years, when he is 31 and already filthy rich, he can sign a Werth-ian deal.

      • uyf1950 - Jul 21, 2011 at 2:34 PM

        Both you gentlemen may very well be correct. I happen to believe and this is just my personal opinion that the greater the risk the greater the reward…and should Ellsbury continue to perform at a high level up to FA he most certainly will reap the benefits. And I think all of us on this board knowing what we do about Boras he isn’t about to leave money on the table. Sure there are risks in Ellsbury not signing a long term deal until FA. But I’m not naive enough to think that buy the Sox signing Ellsbury early for less money that they (Sox) don’t benefit from the deal more then Ellsbury. I guess we will all see how this plays out in the months and years ahead.

      • Chris Fiorentino - Jul 21, 2011 at 2:49 PM

        Oh I agree 100% that the Red Sox get something out of it…namely, Ellsbury at a discount for 2 years. However, Ellsbury also gets financial security for life 2 years early. It’s a trade-off. Either way, it’s Ellsbury’s decision. Bor-ass is just a guide. Even if he says what he thinks they should do, it isn’t like Ellsbury can’t say no. So Bor-ass doesn’t deserve all the grief.

      • bigharold - Jul 21, 2011 at 4:02 PM

        “But why risk it? And the best part? If he stays healthy and earns the cash, then in 4 years, when he is 31 and already filthy rich, …”

        Perhaps but his agent is also Johnny Damon’s agent. The same Johnny Damon that got to 31-32 years old and the RS told him to take a hike.

        UYF has a point. Both Crawford and Elsbury are the same type of player. Right now, at least, Elsbury is out playing him by a wide margin. Why would or should he sign away the 5 most productive years of his career for a third of what they just gave Crawford. Even if one were to conclude that Elsbury is not a better player and will not have a better career he is certainly better than one third the what the RS are currently paying their LFer.

        Is it a risk, .. absolutely. But, for what can be gained it is one worth taking because the payoff should be at least twice as much as the conventional wisdom seems to think the RS are currently considering giving him.

        Boras is one of the better agents in baseball and I can’t imagine him telling Elsbury “yeah, take what you can get, 50 mil for the next 5 years because waiting two for a a crack at 100+ mil is just not worth the risk.” Baseball players don’t get to the major league not believing in their ability. Boras didn’t become one of the better agents in baseball playing it safe.

      • Chris Fiorentino - Jul 21, 2011 at 4:12 PM

        big, I agree with your take 100% regarding what Bor-ass will advise Ellsbury. I am simply talking about why Ellsbury should take the guaranteed money. Many players do it. They decide against the risk and take the life-changing money and sacrifice 2 years of FA. At 31, if he plays up to his potential, he would get Crawford money. If he doesn’t sign now, and gets hurt in the next 2 years, he never gets even life-changing money.

        And don’t woe-is-me Damon…the RS didn’t want to pay poor Johnny Damon $52 million over 4 years, while the Yankees did. So don’t cry a river for poor old Johnny.

      • spindervish - Jul 21, 2011 at 4:19 PM

        At the risk of repeating myself…you’re sort of missing the point. Ellsbury to Crawford is not a fair comparison for one simple reason: Ellsbury is two years away from free agency.

        Obviously he’s been far more valuable than Crawford this year, and at this rate he might even end up being more valuable over the next 2-4 years. But because of baseball’s current compensation system, there is just no way Ellsbury can expect to make a salary comparable to a top-level FA over the next two years. So whether he opts for some long-term security or chooses to go year-to-year, there’s just no way he’s getting fair value for his services until 2014. Once you accept that fact, the idea of giving up a year or two of free agency in return for that long-term security seems a lot more palatable.

        I would probably tend to agree that, given his agent, he’s pretty likely to risk the year-to-year thing. But the idea that Crawford’s current salary is a major factor seems pretty wrong. Ellsbury has no business comparing his earning power for the next two seasons to Crawford’s.

  5. uyf1950 - Jul 21, 2011 at 6:23 PM

    spindervish – I may be missing your point but I know you’ve missed mine. I wasn’t saying Ellsbury should compare his earning power/potential for the next 2 years to Crawfords. What I was saying and am saying again is why in the world should Ellsbry give up 2 years of FA earnings just so the Red Sox can have a home town discount for those years. Because of the nature of the “collective bargaining beast” the Red Sox will be getting a “home town” discount on Ellsbury for the 2 years remaining that he is arbitration eligible. That’s all I’m saying.
    Also, may I say one other thing and this is just a personal observation on my part and is not directed to spindervish. But the comment that has been made about a “life altering deal” if he were to sign a 4 year extension. As a person who worked for over 35 years in what I like to call the “real world”, all of these ballplayers as soon as they have signed on the dotted line for anything over what 98% of the working class makes has already made a life altering deal. After that it just becomes “funny money” from my perspective. That’s just my feeling.

    • spindervish - Jul 22, 2011 at 9:42 AM

      For the sake of clarity — my second response wasn’t directed to you but to the other guy comparing Ellsbury’s value to Crawford’s. I saw your response and found no reason to believe you had missed any point I attempted to make. That said, your last post does give me pause.

      As I attempted to point out before, because Ellsbury’s expected earnings the next two years will be below fair market value, it doesn’t really work to look at a theoretical 4-year, $50 mil deal and say he’d be making $12.5 mil a year for his first two years of FA and thus would be giving the Sox a “hometown discount.” In fact the deal likely wouldn’t even be structured like that; his yearly salary would be scaled. So he’d be making something closer to $18 mil a year for his first two years of FA, which as I said, is pretty damn competitive. All the deal would accomplish would be locking in his arbitration years at reasonable arbitration-rate estimates and then his first two years of FA at something at least approaching fair market value. I don’t really see any “hometown discount” in this scenario. The major advantage from the team’s perspective (besides the budget certainty) would be not having to lock him up for, say, 6 years of FA, thus incurring more risk. They get two prime FA years at competitive FA prices, and then can reevaluate after that.

      The reason, I think, that agents like Boras are loathe to do deals like this is that it amounts to a 2-year FA contract for a player in his prime, when waiting until the player actually hits FA could easily net him a 4-6 year deal. So I don’t think it’s so much a case of sacrificing yearly salary as it is sacrificing guaranteed years.

      And of course, the answer to your question of why any player would want to do this is simple: financial security. If this doesn’t move you, that’s fine…apparently it doesn’t really move Boras either, and he seems to know what he’s doing.

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