Chicago Cubs: What will Theo Epstein’s contract extension look like?

With one year left on his deal, the Chicago Cubs’ biggest offseason deal could be a contract extension for president Theo Epstein.

Prior to the team’s thrilling postseason run, Tom Ricketts, owner of the Chicago Cubs, talked with members of the media about a pressing matter: bringing back president of baseball operations Theo Epstein.

"“We haven’t had a conversation about that, but we’ll certainly get to that pretty soon here and make sure we do the right thing for everybody,” Ricketts told 670 AM The Score in September."

The combination of the Ricketts family and Epstein has been pure gold: the Cubs have become a powerhouse, while Wrigley Field continues to improve this offseason, benefiting both fans and players alike. Not to mention the fact that radio broadcasts are moving to a major sports network in 670 and the team is expected to be active in the market this offseason.

Chicago won 97 games this season, advancing to its first National League Championship Series since 2003 before falling to the New York Mets. Already this offseason, the team has been connected to top-tier free agents such as Zack Greinke, David Price and Jason Heyward – although lesser-known targets seem more likely.

So what’s next for the man pulling all the strings?

There’s little doubt the Chicago Cubs will bring their man back long-term. This is just the beginning of a relationship that’s clearly benefitted both sides since its inception a few years back. And that’s a point that was made by Theo at season’s end, as well.

"“I ended up staying 10 years in Boston,” Epstein said. “It was nine as GM, but 10 years there. That seemed about right, long enough to try to make a difference and try to contribute to winning teams and some championships. We have a lot of work left to do here."

Championships. Winning.

Those are words Cubs fans are, at long-last, becoming familiar with once again.

And it’s thanks to Theo Epstein.

So what will his next deal look like? I anticipate another five-year pact that exceeds the one given to Los Angeles Dodgers president of baseball operations Andrew Friedman last offseason, which spanned five years and totaled $35 million. I’d expect, at a minimum, $40 million – but I imagine Ricketts will give Theo a blank check to finish the job he’s started at the Friendly Confines.

After leading the Boston Red Sox to a curse-crushing World Series title in 2004 and another championship in 2007, Epstein already holds a cemented spot in baseball lore. Adding the defeat of the Curse of the Goat to his resume would make him not just one of the best front office executives in MLB history, but one of the best sports executives in history.

Of course, that comes with a cost. But if there’s anything the Ricketts family has shown us in their brief time atop the Chicago Cubs’ hierarchy, it’s that they’re willing to pay the price for success – and there’s no better man to help guide that ship than Theo Epstein.