Boston Red Sox GM Theo Epstein remains the longest of long-shots for the Chicago Cubs’ open GM gig, but his name isn’t falling off the radar quite yet, particularly after his tepid denial of interest a couple weeks ago.

This weekend, both Nick Cafardo of the Boston Globe and Phil Rogers of the Chicago Tribune expressed a belief that there may be a tiny kernel of something to the Epstein rumors, and neither expects those rumors to die down any time soon.

First, Rogers:

Around baseball, there’s a belief Ricketts might hit a home run, possibly even persuading Epstein to leave the Red Sox after nine seasons and two World Series parades. It’s easy to see the downside with an organization that last won it all in 1908, but the perception outside Chicago is different.

“People in baseball talk about it like it’s the Holy Grail right now,” one major league executive said. “You have a chance to break a curse that’s longer than the one the Red Sox ended. You can distinguish yourself in ways that aren’t available elsewhere.”

Epstein is 37, and he essentially already has done it all for the Red Sox. Does he want to stay in his hometown and try to operate an assembly line for fans who become more demanding with each playoff trip? Could he be seduced by the chance to do it again at Wrigley Field?

That’s what Ricketts is waiting to find out, and some close to Epstein believe he’s intrigued. Epstein has said he’s “completely focused on the Red Sox of 2011” but has not dismissed Ricketts’ interest …. [E]xpect Ricketts to call Red Sox owner John Henry or Epstein a day after the Red Sox’s season ends.

Rogers says he’s also heard that Epstein is “bored in Boston,” which would make Chicago the ultimate pick-me-up. Even if it isn’t Epstein, Rogers expects Tom Ricketts to take him time and make a real run at the “long-shots” (Epstein, Brian Cashman, Andrew Friedman, and Billy Beane) before moving on to the second tier of candidates, even if it means not having a new regime in place until November.

Cafardo is less bold than Rogers, but leaves the door open on Epstein-to-Chicago:

There will be denials from here to Timbuktu, but the baseball community has not dropped the Theo Epstein-to-Chicago talk. And until Cubs owner Tom Ricketts selects a new president of baseball operations or general manager – or Epstein agrees to a contract extension with the Red Sox – the rumors likely won’t die.

The Sox have Epstein under contract for another year, but it isn’t clear whether he is free to leave for a bigger job ….

As one AL GM pointed out, “The Cubs job is the prize because it’s a great city, and the owner seems to want to spend the money to make it right.’’

In other words, though Epstein may not ultimately come to the Cubs, it isn’t insane to speculate that he might. The Cubs job, despite the organization’s recent (and long-term) struggles, is profoundly attractive to both established GMs and up-and-comers. Flatly ruling anyone out without more justification than “why would he leave Team X for the Cubs?” is naive.

That all said, while Epstein remains the prized pig for the Chicago Cubs, I can’t shake the feeling that he is wisely using the Cubs’ opening as leverage to squeeze more money, a better title, or both, out of Red Sox ownership. So, although it may be premature to flatly rule Epstein out, other than vague whispers and a thin denial of interest, there is little reason to believe Epstein would actually pack up his bags and leave Boston.

But, if he is interesting, I’ll gladly help him pack.

  • Internet Random

    As I’ve said before, it’s very, very difficult to ignore piles of money.  Couple that with the chance of making a large, indelible mark in the history books, and I think we’d be fools to rule out Epstein.  Is he the most probable candidate?  Not right now, but that doesn’t make it highly unlikely either.

  • Baseballet

    Epstein and his hair would probably only be willing to come to the Cubs if he would be okay with GM’ing a bad team for a few years.  Even if you added Fielder and CJ Wilson to this year’s team, the Cubs still wouldn’t be a top candidate for a World Series.  And our AAA team doesn’t seem to have any stars-in-waiting to help make the Cubs relevant in the near future.  (It’s going to be a while before the Shawonometer Jr. starts tracking Dunston Jr.’s major league batting average.)

    Is he willing to wait for his first gray hair in order to win his next World Series?

  • EQ76

    The key thing I heard was “He might be bored in Boston”..

  • Baseballet

    I see from Wikipedia that Epstein has a twin brother Paul.  Why don’t we just get him as GM?  It’s like getting RFK instead of JFK.  Not too shabby.  Theo also has a sister, Anya, who wrote for the TV show “Homicide: Life on the Streets” so she knows a little something about tough situations going down on the mean streets.  Let’s get her managing in the dugout, taking care of business.

  • T Wags

    I dont know much about Theo Epstein other than he’s wildly successful for the Red Sox and that i would love to have him in our front office by November. Having said that, from what i’ve read online i get the impression that he is in fact bored in Boston and wants to run his own show/ move onto a new challenge and dear God I hope I’m right. Money is very powerful and Tom Ricketts has a lot of it and wants to win as much as any of us do. Also, you know there’s a little voice in the back of Theo’s head saying “You do realize that if you go to Chicago and kill that billy goat the Hall Of Fame is waiting…” Not to mention Legend status in Chicago Sports which I’m assuming is pretty awesome. Just ask Ditka and Jordan….

  • hansman1982

    So which is better – Boston not making the playoffs or Boston winning the WS this year for our chances in landing Epstein?

    • Brett

      That is a very interesting question right there. I could see either way.

      • hansman1982

        God, you are a lawyer…

        HA, I think it would best for them to make it and get beat out in 5 games in the ALDS – this way he doesnt appear to be running from a collapse and Tom will have plenty of time to woo him.

        But going with one extremem or the other – WS for me.

    • T Wags

      I honestly believe the end result of the Red Sox’s season will have zero effect on what Theo decides to do. At this point he has nothing to prove in Boston. If they win it all again will it really feel as sweet for him as the first or even second one did? I doubt it. All that will do is drive up expectations even more, and he may feed off those expectations i dont know. If they dont make the playoffs (which is very unlikely) and he hears the outcry from disappointed fans, he may take that as a challenge for next year or he could be thinking “Wtf do you want from me i gave you 2 WS championships after you suffered for 86 years, give me a break.” If i had to choose one though I’d say missing the playoffs which will give us a bigger time window to woo him away..

    • Dan0mite

      I was jut gonna make a post about this. The Sox are 3.5 back of the Yankees and only 3.5 ahead of Tampa for the wild card. The Sox are struggling and the Rays are picking up steam it is a real possibility that the Sox don’t make the play offs. I think that could help the Cubs.

      The fans and owners may be mad that the Sox crashed and burned so late in the season. Also, without the playoffs Theo won’t have to be fully focused on the 2011 Red Sox. Ricketts may have a bit more time to lure Theo away.

  • Matt

    I just had that very conversation with a co-worker. I worry that if Boston does not make the playoffs, Epstein may be worried about his appearence in Boston of “running away” from the Sox after falling out of the race in the final weeks.

    • T Wags

      Good point Matt. Nobody wants to ruin their hometown image… And i didn’t know the wildcard race was that close i guess it’s been awhile since I’ve looked at the standings. After all, I am a Cubs fan… smh

    • hardtop

      then he should take the job now…  while they are still in the wild card, that way he can say:

      “sheeit bitch, who be runnin away? we were leadin the damn wild card race when i left, i gots nuffin to run from! damn, fooz!”

      • EQ76

        I had no idea Theo spoke in ebonics.  He just gained some serious street cred on that one.

  • Cubs_Fanatic

    I’d be happy with Theo. I mean he couldn’t do worse than Hendry. So I’m all for this.

  • DaveB23

    Not sure how reliable of a source Rogers is, but if he’s right about Ricketts being willing to wait in order to make a run at the top-tier candidates (Theo, Friedman, Cashman) even if it means waiting until November, this is great news.
    Hopefully that means Ricketts would also be willing to give up his self-appointment of the President of Baseball ops role, if that’s what it took to land Epstein…