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?


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