The Curious Case Of Compensation For Theo Epstein

The scoreboard in the bleacher seats displays the interleague matchup at Fenway Park in Boston, Massachusetts between the Chicago Cubs and the Boston Red Sox. (Photo by Elsa/Getty Images)

The Cubs and Red Sox are working out compensation for the Cubs' hire of Theo Epstein to be their general manager. The teams, in uncharted waters, have yet to come to an agreement.

Theo Epstein is going to be the new general manager of the Chicago Cubs. We know this because we have seen many tweets, television reports and articles both in print and online on this topic.

There has been no official announcement from the Red Sox that Epstein is leaving; one report said it was "business as usual" along Yawkey Way in Boston. We have seen no announcement from the Cubs that they have officially brought Epstein in; no news conference has been scheduled and the team isn't talking.

What's the holdup? Epstein is still under contract to the Red Sox and ownership is demanding some form of compensation for letting him go. This sort of thing has been done for non-players in the past -- just a couple of weeks ago the Marlins sent a couple of middling prospects to the White Sox so that they could sign Ozzie Guillen as their manager.

With both teams in uncharted waters, I thought it would be useful to examine what they want. Thursday night, it was reported that negotiations had hit a "bump". Two further reports, one from Chicago and one from Boston, lay out some of the issues.


A major league source said late Thursday one of the holdups is the Cubs' insistence on paying only cash for compensation while the Red Sox are adamant on receiving a player or a package of players.


The Red Sox are expected to get either cash or two or three minor league prospects in return for their general manager, who is still under contract to them for one more year. The quality of those prospects could be tied to how many front office staffers are allowed to accompany Epstein to Chicago.

Who could these players be?


Triple-A Iowa outfielder Brett Jackson, a first-round pick in 2009 currently playing for the U.S. national team, figures to be at or near the top of Lucchino's list. Jackson is one of a trio of prospects the Cubs probably would deem untouchable, along with Class-A outfielder Matt Szczur and Double-A right-hander Trey McNutt.


The Cubs’ farm system is largely bereft of talent, but there are several players who could interest the Red Sox. Outfielders Brett Jackson and Matt Szczur are highly regarded. Righthanders Alberto Cabrera and Jay Jackson are possibilities. Chicago’s top pitching prospect, Trey McNutt, dealt with injuries this season but could be on the table.

The two writers are mostly in agreement there. Further...


While Epstein can't play a role in the de facto trade of himself, it's obviously in his best interests to keep the best prospects in a farm system already thinned out by last January's Matt Garza deal.


There are no indications that the Red Sox will be able to unload a bad contract on the Cubs - ahem, John Lackey - as part of the compensation package.

Although, surely Boston would love to do that.

There are also no indications that this deal won't get done. Given the dysfunction revealed surrounding the Red Sox, Epstein's reported desire to leave and the reports Thursday that Ben Cherington has already been told he'll be Boston's next GM, it seems clear that John Henry and Larry Lucchino want Theo gone. And if Cubs chairman Tom Ricketts doesn't get this done, given the bliss Cubs fans are already showing about this move, angry mobs with torches and pitchforks might descend on his Wrigley Field office. It probably won't involve Brett Jackson, Szczur, McNutt or Cabrera; it could involve Jay Jackson plus perhaps another lower-level prospect and some cash to finalize this unique deal.

There's one last thing from the Boston article worth mentioning. It quotes Seth Mnookin, who wrote a book about the Boston front office in 2006:

"It’s a double-edged sword for him, working in Boston," Mnookin said. "He’s the only GM in the country who can’t have a peaceful dinner out if he wants.

"Chicago won’t be the same. It won’t be the same story line in Chicago as it is in Boston. He won’t be the guy who grew up a few blocks from the ballpark.

"The attention, the scrutiny, it won’t be a 365-day thing for him. There won’t be the public expectations and the media expectations."

Once the teams settle on compensation, Epstein will find out that expectations from Cubs fans and Chicago media will indeed be sky-high for him. He'll be a celebrity of the first order in Chicago and the pressure on him will be immense. Be careful what you wish for.

Latest News

In This Article

Log In Sign Up

Log In Sign Up

Forgot password?

We'll email you a reset link.

If you signed up using a 3rd party account like Facebook or Twitter, please login with it instead.

Forgot password?

Try another email?

Almost done,

By becoming a registered user, you are also agreeing to our Terms and confirming that you have read our Privacy Policy.


You must be a member of to participate.

We have our own Community Guidelines at You should read them.


You must be a member of to participate.

We have our own Community Guidelines at You should read them.




Choose an available username to complete sign up.

In order to provide our users with a better overall experience, we ask for more information from Facebook when using it to login so that we can learn more about our audience and provide you with the best possible experience. We do not store specific user data and the sharing of it is not required to login with Facebook.