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Compensation is the issue now

THEO EPSTEIN What is he worth? THEO EPSTEIN What is he worth?
By Peter Abraham and Nick Cafardo
Globe Staff / October 14, 2011

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The slow process of Theo Epstein moving from the Red Sox to the Chicago Cubs continued yesterday as representatives of the teams discussed compensation.

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.

Epstein’s top assistant, Ben Cherington, and Cubs assistant GM Randy Bush are negotiating the deal, which must be approved at the ownership level.

Once Epstein’s move becomes official, the Red Sox will name Cherington as his replacement. Cherington has been guiding the baseball operations department for much of this month as Epstein dealt with the Cubs and worked out the details on a five-year, $18.5 million deal.

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.

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.

Epstein’s soon-to-be-official departure from the Red Sox did not come as a surprise to author Seth Mnookin, who spent more than a year embedded in the Sox front office researching his 2006 book “Feeding The Monster.’’

He believes Epstein grew tired of the atmosphere in Boston and that his personal ambitions trumped hometown loyalty.

“Theo had two world championships with the Sox,’’ said Mnookin. “Any kind of similar success with the Cubs and he’ll go down as one of the most accomplished general managers in baseball history. It’s a hard challenge to turn down.’’

With the Cubs, Epstein is expected to have a position on par with team president Crane Kenney. That was not available with the Red Sox because of the presence of Larry Lucchino.

“He’s hit a ceiling as far as the actual job he can do with the Red Sox,’’ Mnookin said. “[Red Sox owner John Henry] has enormous respect for Theo and for Larry. Larry is going to be there. What he has done with his end in terms of building the business side and building the fan base is incredible.

“For Theo, what can he do to top what he’s done? Unless they win the Series, the season is perceived as a failure. Unless he can win five in a row or something, there’s nothing he can do to make people stop in the street like they did a few years ago.

“My impression when I was there was that he was frustrated by the expectations that everything would be on a straight upward trajectory.’’

Mnookin believes that Epstein’s move is also being made for personal reasons. Friends of Epstein, including NESN’s Peter Gammons, have made the same point.

“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.’’

Peter Abraham can be reached at pabraham@globe.com. Follow him on Twitter @PeteAbe.

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