There comes a point in any wildly successful professional life where money tends not to matter. No, if you’re successful enough in a high profile field, two things emerge as your primary motivators. The first, of course, is happiness. When money is no longer a concern, you can make professional decisions based on, for example, where you’d like to live, how much you’d like to work, and what you enjoy doing.

The other primary motivator for such people? Legacy.

That’s why I’m not convinced that Boston Red Sox General Manager Theo Epstein would completely dismiss the opportunity to come to the Chicago Cubs out of hand.

Sure, the Red Sox can raise his pay. Even if the Cubs couldn’t match whatever the Red Sox offered (they could), is money really going to make Epstein’s decision?

Still, I have no reason to doubt that Epstein is happy in Boston. It is his hometown. His family is there. He’s a hero beyond words to the legions of Red Sox fans. So, if money is out of the equation, and we’re looking only at the happiness motivator, I understand that Epstein would be a longshot to leave.

But what about that other motivator?

Imagine you are Epstein. Your legacy is already impressive, having pieced together the Red Sox team that finally broke the Curse of the Bambino, and won the city’s first World Series in some 85 years. You feel pretty good about yourself. In Boston, you will always be a legend.

The rest of the baseball world will probably remember you. Perhaps even fondly. Of course, the Red Sox spend a whole lot of money in the 2000s, they’ll say, so how much credit goes to you, and how much goes to the owners? Were the Red Sox bound to win it anyway? Were you really the deciding factor between victory and defeat? You might never know for sure. And neither will those who question you.

But if you came to the Chicago Cubs – a franchise perhaps more tortured than your own – and put together a World Champion?

Three words: Hall of Fame.

Maybe more than that. I think you could make a fair argument that the guy who finally won it all with the Red Sox, and then finally won it all with the Cubs, is the best executive in the history of baseball. Setting aside money and happiness (such as it is possible to do so), isn’t that a legacy worth considering?

  • MontelleW

    I dont know whether to be excited or not when i read that – the thought of having Epstein come here and win it all gets me so excited that I salivate, but I hate to get my hopes up in case we end up with a Ned Colletti instead!

    • Brett

      I should emphasize: Epstein is an extreme longshot.

      But I don’t think Colletti is much more likely.

      • CubFan Paul

        i’ve seen talk of Epstein being interested if he were offered the “President” title with a GM under him & that makes Brett’s arguement/point more valid because Epstein isn’t the “Boss” in Boston and could be in Chicago, thats why i don’t think its an extreme longshot

      • dreese

        I have been reading a lot about probable GMs (exciting!!) and I really am hoping Ned Colletti is like Ricketts back-up, back-up.

  • Fishin Phil

    I’m sorry, but I just can’t see Epstein making the move. I’d love to be wrong, but I don’t think I am.

  • TheBigMustafa

    He’s already won two World Series Championships in Boston. He can get to the HOF without the Cubs.

    • Brett

      Of course he can. And might. But doing it with the Cubs not only ensures it, but it places him among the discussion for best of all time. Is he in that discussion today?

  • Spencer

    I agree that his legacy would be cemented if he came to Chicago and won. And that thought for him might be very enticing. But, I think if he left Boston he would be despised by everyone in that city, and that might not be something he wants on his legacy either. Plus, he actually has to WIN in Chicago, which really isn’t something lots of people have done. So I guess there are lots of pros and cons he has to weigh.

  • EQ

    I still think Gillick is viewed as a more reasonable favorite if it’s a prez/GM gig.. Epstein would be great but seems like a dream more than a reality.. hard to imagine him leaving Boston for any reason.. that may be the top GM job in the bigs.

    • Brett

      I think Ricketts views himself as the favorite for the baseball president type gig. And, increasingly, I think he’ll be a good fit.

      • Michael

        Considering this statement alongside your view that Ricketts is methodically going about implementing his vision for the franchise, would you surmise that Ricketts is retaining Kenney while continuing to learn the business side of the franchise with hopes of elevating his level of self-confidence in order to simply not resign Kenney after next year and assume the role himself? That, of course, would position Ricketts as the boss over his hand-picked GM who has had a year in the bag with the franchise, scouts and stats.

        • Brett

          I don’t know about that precise setup, but there are people who believe Ricketts is retaining Kenney only long enough to secure public funding for Wrigley.

          • Jeff

            From things I’ve read, and taking hints from what Rickett’s has been saying, I think Kenney is team president in name only. He handles some of the business, and has a relationship with the Chicago politicians, so I do some validity to what you’re saying about the funding Brett.

            Ned Colletti gets a hell no, Theo Epstein is a great choice, but I don’t think he’s going to leave Boston, whether the motivation was money or prestige, I think he’s happy there. I do support Ben Cherington. I think he fits the Epstein mold without the hype and expectations that Theo would bring. He was GM of the Sox for a bit while Epstein was taking his sabbatical, so he has experience in the kind of environment that Chicago is. I never thought I’d be so excited to see the Cubs interview and talk about a bunch of stuffy white guys in suits, but here we are.

  • Toosh

    I’m thinking that maybe making the Hall of Fame someday is not something that GMs think about much. If ever.

    • Brett

      Not if you’re John Mozeliak. But if you’re Theo Epstein and you’re specifically pondering a move to the Cubs? I guarantee, under those circumstances, the Hall of Fame would enter into your mind.

      • Toosh


        • Brett

          Well, at least you’ve supported your position with well-explained line of reasoning.

          I’m convinced.

  • hansman1982

    I dont want him…the butt chin reminds me too much of Tom Brady…

  • Toosh

    Sorry, Brett. I just find it hard to believe that a successful, young GM would spend any time thinking about maybe getting chosen for entry into the Hall of Fame. And for you to guarantee it, no matter what the circumstances, is ridiculous.

    • Brett

      Nobody is talking about him doodling “HOF-4-Eva” in his spiral-bound notebook every day. I’m saying – and, yes, I *guarantee it* – that when it comes to thinking about leaving Boston to join the Cubs, of COURSE the HOF would enter his mind, even if fleetingly. In what universe wouldn’t it?

  • Toosh

    In the universe where, when people are in the midst of a successful career, they say to themselves “Hmm, I’ve been pretty successful so far. If it continues, maybe I’ll make The Hall of Fame”. Sorry, I don’t see Epstein thinking that. Looks like we agree to disagree.

    • Brett

      I disagree to disagree.

  • Lou

    I don’t think he’ll come here. But then again, neither will Rick Hahn, Andrew Friedman, nor Brian Cashman. Think Beane will get a shot or an executive. Like I’ve said, Shapiro from Cleveland or I’ve also heard, Beinfest from Florida. Though don’t know much about Beinfest.

    • hardtop

      Rick Hahn would rather sit in a “cell” on the Southside than be the GM for a top 5 market team? I’m not sure I buy that? Same with Freidman: if he believes he’s good at what he does, than why would you stay with Tampa or go to Houston when you could have a huge payroll on one of the countries most popular teams? I’m not saying you’re wrong; I just would like to here your reasons for making this declaration with such certainty?

      • Lou

        It’s all about fit and how scenarios play out internally within teams. Rick Hahn could potentially be a GM for a top-market team. Why would the Sox let him go and rebuild the Cubs on the North Side after grooming him to be GM with their team? Lots of internal problems going within that team (the White Sox). I see Kenny Williams relinquishing his role within the Sox as GM and Hahn taking over that position as Williams takes on another spot. Look at all the bad contract decisions he’s made. That being said, Reinsdorf still likes Williams. If the Red Sox win another WS, why would they let Epstein go? He’s basically revered there. He could easily move up to head of baseball ops there (he would want another challenge given that he’s done all he could as GM), giving Cherington, another person groomed to be GM, the position. After all, Cherington’s been with the Red Sox for 10+ years. As for Friedman, same thing. If you’re a owner with a close, special relationship with him, why would let him go? Teams covet certain players. Well, teams covet certain personnel. Simple as that.

  • hansman1982

    If the past two years are correct I think the GM search will drag until the very first part of November and it will be a great pick after Cashman, Friedman and Epstein are ruled out.

    For those of you who doubt Epstein would come here to try to win a WS and cement his legacy, I don’t think that Brett is saying that would be Epstein’s only motivator just a part of the puzzle. I am also guessing that you have never been at the pinnicle of success in your respective career nor does your career field have a HoF.

  • Toosh

    True on both points.

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