Theo OK with doing business with Boston

Theo Epstein said he talks to Ben Cherington all the time and would feel comfortable making a deal. Getty Images

Baseball executives since the 1930s have moved from franchise to franchise to revitalize downtrodden teams. Such is the case in Chicago, where Theo Epstein hopes to perform the same magic that produced two world championships in Boston.

In order to rebuild the Cubs, Epstein and general manager Jed Hoyer will make some crucial moves over the next six weeks in trying to acquire 5-to-8 young players for starters Ryan Dempster and Matt Garza.

No team in baseball needs starting pitching more than Epstein's former club. The two franchises have completed two minor deals in the six months since Epstein left the Red Sox, but with some acrimony over the compensation issue Boston received for Epstein, some wonder if the two franchises could complete a blockbuster deal involving players Epstein once drafted.

"I don't know what the next three weeks will bring but we already made two deals , one complicated (compensation ) and one pretty easy (Marlon Byrd for Michael Bowden)," Epstein said before the Cubs hosted Boston on Friday. "We talk (with Red Sox GM Ben Cherington) all the time, so it always makes it easier to do a deal when you have a good relationship with the other party."

The Red Sox have a treasure trove of good young prospects at the lower levels that the Cubs would love to get their hands on, and clearly the Red Sox need pitching now in order to win the toughest division in baseball. Ten to twelve clubs will be watching all of Dempster and Garza's starts, and scouts are split on who they would prefer in a trade.

"Stuff wise, it's Garza hands down -- that's who you want," said an American League talent evaluator. "Dempster brings a whole lot more to a team than just pitching every five days. You really are going to be fine with either one depending on what you have to give up. "