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Come Fan with UsMonday, June 22, 2026

The Price To Pay For Theo Epstein

What the Red Sox should be asking the Cubs for in return for talking to their current GM, Theo Epstein.

The Cubs have not won a World Series since 1908, while Red Sox general manager Theo Epstein has put together two teams in the last eight years that have come away with a championship. Prior to that, though, it had been 86 years in Boston without a World Series victory. It's no wonder the Cubs are interested in talking to Epstein about leaving Boston to become their new GM, and it's likely that they are willing to do literally anything to get their hands on him and change their fortunes, short of an actual deal with the devil. That's a theory that should be tested, though: the Red Sox should hand over a list of ridiculous demands to see how desperate the Cubs are, demands such as:

  • The Cubs must pay $51 million to the Red Sox, upfront, just for the right to negotiate with Theo Epstein. This will get the Red Sox back the money spent on Daisuke Matsuzaka's posting fee, which owner John Henry will then use to buy an arena football team -- giving him one more franchise in a sport that no one in New England pays attention to -- to go along with his racing and soccer teams. Unlike the posting fee, however, the Cubs will not get this money back should they fail to convince Theo to join. For once in their organization's life, they'll need to close the deal before it's too late.
  • Epstein is not the Cubs' permanent general manager. In the event that they win a World Series under him, he is to be sent back to Boston where he will be greeted with a hero's welcome, and reinstated in his old position. It may seem like this is being done solely so that the talk-radio crowd is silenced and is once again in awe of Epstein, but... okay, that's really the only reason to do this. The Red Sox win either way, as, if Theo fails to secure a World Series title, Boston's management will look brilliant for letting him walk. Hooray for perception!
  • Terry Francona is to be hired as the Cubs' new manager, and the same stipulations surrounding Theo and a World Series title will apply to Tito as well. Boston will worry about firing whomever his replacement is when the time comes, but that shouldn't be a problem, as they have ways of making managers disappear.
  • Dan Shaughnessy is to be given a luxury apartment in Chicago as well as a cushy writing job at the local newspaper of your choice. He is automatically entitled to any and all curse-related materials for book-writing purposes, as the 2004 World Series victory in Boston has deprived him of that topic for years. If the Cubs do win a World Series, you can keep him. No, really, we insist.
  • John Lackey and Theo are a package deal. There is no way around this. The remaining three years and $48 million on his contract are Chicago's to pay for and live through. Don't worry, it's not all bad -- this is just going to be Theo's reminder to himself that five-year deals for free-agent pitchers are generally a bad idea. You know, for when Matt Garza becomes a 30-year-old free agent in 2014.
  • Promising young Starlin Castro will be Boston's new shortstop. If this is not possible, then the Cubs are responsible for taking Boston's next five-year pitcher contract off of their hands, as the Red Sox will have forgotten how bad of an idea those are without Lackey around to remind them.
  • Get Chris Archer back from the Tampa Bay Rays, and then send him to Boston. Why Archer, you ask? Solely for the purpose of photoshopping his picture and nicknaming him "Duchess," of course:

It pains me that Rays' bloggers might have the opportunity to do this all the time, and I don't.


Rob Neyer: So What Is Theo Epstein Really Worth ... To The Cubs?

  • Speaking of self-serving demands, attached as a rider on this contract between Boston and Chicago: the Cubs have to pay for my new Red Sox gear, as the hat I received as a gift before the 2010 season clearly isn’t working out and needs to be replaced. For however long Theo remains in Chicago, the Cubs are responsible for any and all Red Sox-related purchases I make. (This includes, but is not limited to, the Red Sox themselves. Get-rich-quick scheme, here I come.)
  • And last, but not least, Wrigley Field is to be destroyed. Immediately. It’s nothing against Wrigley, but Boston loves Fenway Park, and hates the thought that any other park could be as old, friendly, or revered as their own. Wrigley, which will celebrate its own centennial just two years after the now 99-year-old Fenway, needs to go before it’s too late. There are future marketing dollars at stake!
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