Theo Epstein to Cubs: Why He Will Ultimately Regret His Move to Chicago

With the very foundation of the Boston Red Sox seemingly crumbling around him, former Red Sox general manager Theo Epstein got out of Dodge by signing a five-year deal worth between $15 million and $20 million with the Chicago Cubs.

It's obvious why the deal was attractive to Epstein as he will likely have a title in Chicago even greater than general manager (with full personnel power), plus he was able to escape from a mess that he was very much responsible for in Boston.

Despite the Red Sox's epic collapse down the stretch, Epstein was likely always going to be beloved to some degree in Boston as he was the general manager responsible for ending "the curse" and bringing a World Series championship to Boston in 2004.

With his move to Chicago comes great expectations, though, and he probably won't be given a great amount of time to turn things around for the stagnant Cubs. In all likelihood Epstein will be given a blank check to go out and sign the players necessary to make the Cubs contenders.

That may mean a player like the St. Louis Cardinals' Albert Pujols or the Milwaukee Brewers' Prince Fielder will be on his radar. That's all well and good, but let's not forget about some of Epsteins's high-priced free-agent flops in Boston.

Starting pitcher John Lackey and outfielder Carl Crawford both come to mind as players that performed well below what their tax brackets would suggest this past season. Despite all of the talent on the team, the Red Sox were unable to bounce back from their poor play.

The Cubs certainly aren't as talented as the Red Sox, though, so a free-agent bust would be incredibly detrimental to the development of the team. Epstein is caught between a rock and a hard place in that he has to improve the team quickly, but be mindful of his spending at the same time.

Epstein obviously deserves some credit for building the Red Sox two World Series winners, but it seems to me like those teams were just the perfect storm. David Ortiz, one of the biggest contributors, was little more than a marginal player in Minnesota. Some may call acquiring him a masterful evaluation by Epstein, but I tend to call it a bit lucky.

There is no question that Epstein will need far more than luck to rebuild the Cubs, though. Epstein hasn't made the greatest personnel decisions in recent years, and his skills will truly be put to the test in Chicago.

Hopefully Epstein enjoys a challenge because he probably won't get more than a couple years to turn the Cubbies around before the faithful get restless. If Epstein succeeds in Chicago, then I'll be willing to admit that he's a great GM, but that has yet to be seen.