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When the Boston Red Sox signed outfield Carl Crawford, then 29, to a seven-year, $142 million contract last Winter, the deal was almost universally derided.

Yes, Crawford was a valuable player and would presumable contribute in a spot of need for the Red Sox, but, as a guy whose primary value is derived from his speed, was it really wise to commit so many years and so much money to a guy who would soon be turning 30? And, frankly, Crawford was never a terribly productive hitter – he was coming off the best season in his career, in which he hit .307/.356/.495. Good numbers, sure. But $142 million numbers? The deal looked horrible.

And then it got worse.

Crawford struggled through a miserable 2011 season that saw him rival Adam Dunn as one of the worst performing newly-signed players in the American League. He hit just .255/.289/.405, and stole just 18 bases. Worse, Crawford’s defense wasn’t particularly impressive.

The next six years of his deal threaten to make him the worst free agent signing of all time, and the involvement of new Cubs’ President Theo Epstein in making that deal cannot be ignored. No one knows for certain who was pushing to sign Crawford so aggressively – there are rumors that Red Sox ownership wanted to sign Crawford to a “whatever it takes” deal as a PR move – but regardless, for Epstein, it’s a black eye.

Would he consider taking that black eye on again?

Executive-cum-analyst Jim Bowden thinks so.

In a video for ESPN, Bowden predicts that Crawford will have a “bounce-back”  year in 2012, but predicts that it will come, in part, with the Chicago Cubs.

“I think by the July 31 trade deadline, the Red Sox and Cubs will work out a deal to send Carl Crawford to the Cubs to play left field at Wrigley Field,” Bowden says.  “I don’t think there’s any question Crawford will hit 20 homers, steal 40 bases, and play plus defense.”

Bowden points out his belief that Red Sox owner John Henry didn’t want to sign Crawford in the first place, and that Epstein is still convinced Crawford will become the player he was expected to be before signing that monster contract. Taken together, Bowden concludes that Epstein will make a move before July 31 to bring Crawford to the Cubs.

There are a couple hurdles to such a deal, of course. Alfonso Soriano is still the Cubs’ left fielder (if in title only), and is owed some $54 million over the next three years. Even if the Cubs move Soriano, would they really be willing to take on another albatross of a contract – given to an aging, slowing, declining veteran – to fill his spot? Crawford is owed about $122 million over the next six years, and, even if he “bounces back,” he won’t come close to providing his team that kind of value. That means, to trade him, the Red Sox would have to either eat a huge amount of that contract, or take on an equally awful deal. I don’t see either route being particularly attractive or likely.

I can hear the suggestion now: just swap Crawford and Soriano. While that might make some superficial sense, I have two problems with it: (1) although Crawford will undoubtedly be the better player over the next three years, I’m not convinced Crawford’s final three years (2015-2017) will be better than Soriano’s coming three years (and that’s really what you’re trading); and (2) relatedly, why kick the salary pain six years down the road when you can be rid of it now, or, at the latest, in three years?

The other possibility – the Red Sox eating a huge amount of Crawford’s contract – could face hurdles with respect to the Cubs. Given the acrimony over Epstein’s departure, and the unprofessional, personal manner in which Red Sox ownership conducted their business affairs, do you really think they would be eager to give Crawford – a player they possibly believe Epstein stuck them with before leaving – to the Cubs for a discount?

So, ultimately, might the Cubs explore a trade for Crawford? I tend to doubt it, but I suppose it’s not implausible if Epstein was indeed the motivating factor behind the Crawford signing.

Hopefully, though, it’s a mistake that he’s learned from, and doesn’t want to duplicate with the Cubs. That goes for new free agent signings, and for re-acquiring Crawford, himself.

  • Dan0mite

    “Executive-cum-analyst Jim Bowden thinks so.”

    So many jokes, so little time.

    • http://www.bleachernation.com Brett

      That’s one of my favorites phrases there – it’s all high falutin, but, like, well, you know.

      • EQ76

        but what do Neal and Bob think?

  • Spencer

    Nailed it. The joke, not signing Crawford.

  • johnbres2

    getting Crawford and his albatross of a contract would be about the single most stupid thing the Cubs could do, which is why I think there is zero chance of it.  Sure, if it could be re-worked, maybe, but how likely is that?  If they got Crawford on bad terms, I would think it would show that the Cubs are still doomed and that nothing has changed….. Not gonna happen.

  • die hard

    All compensation dots now connected. As compensation for Theo, Theo will personally pay $3 mil per year of his own salary to Red Sox to help defray the cost of his decision to saddle them with Crawford.

    • http://www.bleachernation.com Brett

      Sometimes – and I mean SOMEtimes – your trolling makes me chuckle, die hard.

  • DRock

    Absolutely “No.” Crawford is Soriano part 2.

  • Rmay

    Noooooooooooooooooo!

  • nonesuch

    I read somewhere that Cherington pushed to sign Crawford and not really Epstein’s choice. is there any credence to this? even so, the buck stops with Epstein as GM.
    Is Crawford Esptein’s Soriano or is there more to the story?

    • http://www.bleachernation.com Brett

      Cherington did say that at his introductory press conference a few weeks ago, but, while it may have been sincere, I took it as a “I’m the new guy, and I’m not going to pass the buck, so I accept full responsibility.” In any case, as you said, Theo could have said no (unless it was imposed on him by ownership – but no one is talking).

      • Spencer

        I have a hard time believing that an Assistant GM forced a GM who won two World Series titles to sign a guy to a ridiculously high contract.

        • http://www.bleachernation.com Brett

          I don’t think anyone’s saying that – the suggestion is that Crawford was “Cherington’s guy,” whom he fought hard for, and won out in the collaborative decision-making process. And even if that’s true. as has been said, the buck stopped with Epstein, so he bears some responsibility (again, unless it was ownership).

          • nonesuch

            “the buck stopped with Epstein, so he bears some responsibility (again, unless it was ownership).”
            Yeah, but ownership will never “own” up to that. It’s too easy to let the FO guys take the heat.
            If that were the case a lot of internet arguments would be settled about Hendry’s signings.
            We’ll just have to wait for the Oliver Stone movie.
            And if Cherington took the responsibility, it’s probably got traction, he could’ve stayed silent and let the departed Theo look bad. Sometimes a manager is on the fence about a decision and will defer to an assistant knowing he’ll have to support it because he’s in charge.

  • Roland Perrelli

    John Henry did say he did not want to sign Crawford but his Baseball people wanted him so he stayed out of it. By the way Neil and Bob mouths were busy and could not comment.

  • Mike F

    I really think Crawford gets a bad rap based on 1 year. Many would gladly take a real piece of work who has failed defensively back in a heartbeat in Ramirez, and Crawford is a 5 tool guy who didn’t acclimate well to Boston. And Aramis has had more than just a single bad year. Crawford is 30 and Theo projected him well last year, so it makes some sense. If Boston would take Soriano and eat some of the Crwaford’s backend it would be a steal depending on what else was involved. I disagree with the rumored point of view though about a midyear deal. It would be easier to sell this and put this deal together now for a myriad of reasons. If Crawford starts well they won’t trade him. Crawford is cheap at 6 years 120M and his salary as a real 5 tool guy compared to the numbers you’ll see with Pujlois and Fielder. Albert could get 6 years 240 Million and Fielder could get 8 at 200 plus. And both those deals have real risks.

    If Theo and the computer thought he was a good deal then, it’s hard to see how if Boston were willing to take Soriano and some of the back end it wouldn’t be now.

    • http://www.bleachernation.com Brett

      But the thing is, Mike, the deal looked terrible the day it was signed – not just after the terrible year. I think Crawford and the decision that brought him to Boston are getting the rap they deserve. I’m sure, however, he’ll be much more productive in 2012, at least.

  • CubSouth

    “Crawford is cheap at 6 years and 120 million and a real 5 tool player”? Crawford wont put the butts in the seats like Fielder and Pujols and people wanna see homeruns compared to stolen bases. Plus they have better defensive skills. Right now I see Crawford staying in Boston, Pujols in Miami and Fielder in Texas, does anyone agree with me?

    • hansman1982

      no to pujols – he is going to get the dollars he wants so he can be the best paid player in the game from StL with the understanding that he isnt going to get paid all of the contract but rather in 5-6 years he will restructure and get some deferred ownership stock in the Cardinals.

      10 year $300M backloaded

      He plays 5 years – makes $125ish and the other $175M gets turned into owership shares and deferred payments starting at the age of 45 after he resigns a 7-year $110M contract that is front-loaded.

  • Sweetjamesjones

    Brett, your knack for choosing pictures to go with your articles, never ceases to amaze me. The picture of Crawford alone begs for a humorous caption.

    • http://www.bleachernation.com Brett

      It’s the little things, SJJ. The little things.

      Oh, and also, the main, big things.

  • KB

    Bowden is truly speculating out of his a**. We already HAVE an absurdly overpriced LFer in his 30′s who’s main attribute was speed. Why didn’t Bowden just go all the way, and suggest a Crawford/Soriano platoon!
    (actually, if money were absolutely no object, and we enjoyed the idea of an underperforming LFer making $40 million a year, a Crawford/Soriano platoon would actually be the best way to get maximum value out of those two players.)

  • MightyBear

    Theo’s not going to get crawford. I read Theo didn’t want to sign crawford because he thought the contract was too long. That Lucchino convinced Henry to force Theo to get crawford since the Sox didn’t make the playoffs the year before. To me the main reason Theo is in cubby blue, because he couldn’t get along with Lucchino. I can see why. Lucchino’s a prick.

  • Dumpman

    I didn’t like the Crawford deal then, dont like it now, and probably wont like it when its over. I cringed when I saw the deal. I remember thinking that that deal would surpass Soriano’s ridiculous deal in terms of how bad it was. Thats why I’m not a HUGE fan of Theo.. He hasn’t performed well on the free agent market. Think a couple years back. The move he should have made was so obvious. He signed Lacky instead of Holliday. At that very time I thought they should have gone with Holliday instead of Lacky.

    I’m also scared he will give Fielder a huge deal as well. This will be a huge test to see if Boston Theo is here in CHC. I honestly feel Fielder will have a couple good seasons and decline badly. Think Mo Vaughn / Cecil Fielder. That body type historically doesn’t hold up. Sign a Platoon Cust / Gomes 1B for like what, 6m and move foward. Keep Soriano because I doubt we gain much by dealing him.

  • Brian

    There is no way The Cubs should make a trade for Crawford unless the Bo Sox are willing to take all 3 contracts of Soriano, Dempster and Zambrano off The Cubs’ hands.

    • BetterNews

      Regarding Dempster, I like him a person but as a pitcher I think he
      is overated. I know he is a hard worker(there are many hard workers),
      I know he is well liked(there are many likeable folks out there) but
      he is not worth the money he is getting in my eyes.

      Everytime he pitches my blood pressure goes up, I just keep wondering
      when the next pitch winds up in Bleacher Nation!!

      And his woes go back to when he was a reliever.

  • BetterNews

    Brian—Right on bro!

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