Theo Epstein's Chicago Cubs Stint Will Define His Legacy

Theo Epstein's days in the Boston Red Sox' front offices are over, and for good this time. Epstein agreed on a five-year deal reportedly worth nearly $20 million with the Chicago Cubs to become the team's new general manager.

While the news isn't really surprising, as Epstein's potential departure to the Cubs had been rumored since the summer months, it does close a major chapter in the storied history book of the Red Sox. Now that Theo's gone, one of the best decades in franchise history, at least in recent memory, is now a thing of the past.

Before we move forward, let's take a minute to revel in what has been accomplished since 2002. Under Epstein's guidance, the Red Sox have won 932 games and have won 95 games or more games in six seasons. In addition, the team has won 90 or more games in eight seasons.

That success has come from the prospects and players that Epstein either brought up through the farm system or signed in the free agent market. The likes of Kevin Youkilis, Dustin Pedroia, Jonathan Papelbon, Jacoby Ellsbury, Clay Buchholz and so on were all thanks to Epstein and his system. Still, there were plenty of mistakes (mostly on the open free agent market), such as Edgar Renteria, Eric Gagne, Julio Lugo, J.D. Drew, John Smoltz, John Lackey and Carl Crawford, but for the most part, the good outweighs the bad.

Of course, there's the true indicator of a general manager's success: the postseason. Epstein is credited with helping lead the Red Sox to two World Series titles in 2004, which ended an 86-year title drought, and again in 2007. Boston made the playoffs six times in that span and played in four American League Championship Series, winning two of them.

If that isn't a successful tenure with a team, then I don't know what is. Yet that historic period is over for the Red Sox, but the legacy for Epstein is anything but. In many ways, it's just beginning.

Sure, Epstein will go down in history as the general manager who ended the historic Curse of the Bambino in Boston and brought back winning baseball to a city that hadn't seen true success in so many years. But now, Epstein has been presented with another challenge, a task that may be even greater and harder than the one before it.

You ended an 86-year curse, Theo? That's great. Now try ending a 103 year one.

No doubt, this curse will be tougher to end in a city where falling short has become the norm. However, it's not as difficult a task as taking a team like the Kansas City Royals to the top in today's game.

Remember folks, the Chicago Cubs have money, and they are willing to spend it. Last season, the Cubs' payroll was the sixth highest in all of baseball at just over $126 million, so there's definitely capital to work with. 

Still, as Red Sox fans know, money doesn't guarantee victory. If it did, the New York Yankees would be the champs every single season, and the Red Sox would be in the postseason every year (not that I need to point this out, but the Red Sox and their $160 million dollar payoll finished third in the AL East this season and missed the playoffs).

No, it won't be as easy as dolin out the big bucks for Epstein and Cubs ownership. The team will have to make smart moves in free agency and make solid selections in the draft, both of which are things that Epstein has proven he can do, even if they didn't always work out.

If Epstein fails in his new endeavor, he will still be looked upon as a very good general manager, but will still have a smudge on his record for the way his Red Sox career came to a close. But if he can find success with the Cubs and can snap the longest curse in baseball, he will be revered as one of the best all time, maybe even the best.

That's all in Epstein's hands now, and as history has proven, he's certainly capable of doing it.