Baseball executive Theo Epstein has conquered one curse, and he’s poised to try and take down another. He may be leaving the Boston Red Sox at a difficult time, but they’re two world championships richer, and he’s about to take the reins of a franchise that’s also no stranger to dysfunction.

The Chicago Cubs‘ past mirrors the Red Sox’s in many ways — from their historic ballparks to heartbreaking defeats — but the Sox have added relatively recent World Series titles to their legacy. That’s something Cubs fans haven’t seen since 1908.

As Red Sox general manager, Epstein engineered an end to “The Curse of the Bambino” when Boston won its first World Series titles in 86 years in 2004 and then was victorious again in 2007. He is now ready to take over as general manager of the Cubs as soon as the two teams can agree on how the Red Sox will be compensated for allowing him to leave before the end of his contract.

Cubs fans and Chicago ticket brokers are left wondering not only if the “Theo Effect” will pay off in wins, but how will it play at the box office?

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“No one here is going that crazy,” Chicago broker Max Waisvisz, owner of Gold Coast Tickets, told TicketNews, “not until we get some big-name players to go with the big name GM.”

Epstein is leaving one bunch of high-priced underachievers for another. The Red Sox missed the playoffs for the second year in a row after an historic September collapse caused them to blow a nine-game wild card lead.

Epstein’s nine-year tenure in Boston ends amid players admitting to drinking beer during games and ownership reportedly leaking stories that former manager Terry Francona’s lack of discipline had cost him control of an unruly clubhouse and, eventually, his job.

The Cubs are in worse shape. The Red Sox, despite their horrible start and finish, did manage to win 90 games. The Cubs, with the sixth-highest payroll in baseball at $125 million (the Sox were third at $161 million), won only 71 games and finished in fifth place in the NL Central. They missed the playoffs for the third year in a row, and attendance at 41,000-seat Wrigley Field dropped by a total of more than 45,000 for the 2011 season compared to 2010.

It may take more than a curse-busting GM to bring the buzz back to the bleachers at Wrigley.

“Bottom line: if you don’t win, people don’t want to come, and you have season-ticket holders who can’t get rid of their tickets either to us or the general public,” Waisvisz said.

While it was said that Babe Ruth put a hex on the Red Sox, keeping them from a title after Boston sold the Bambino to the Yankees in 1920, the Cubs’ woes are supposedly tied to a billy goat and its owner not being allowed into Wrigley to watch the North Siders’ last World Series appearance in 1945.

The dueling curses had Bucky Dent (1978) and Bill Buckner (1986) supposedly thwarting Red Sox’s title hopes, while the Cubs had a black cat (1969) and Steve Bartman (2003) ruining theirs. It’s up to 103 years and counting in Chicago.

“I don’t know, a lot of damage has been done here,” Waisvisz said, referring to the more realistic curse of poor management and bad contracts that have hindered the Cubs.

Cubs owner Tom Ricketts bought the team from Tribune Company two years ago and has vowed to turn things around. His biggest signing so far might be the acquisition of the man who was the youngest GM in baseball history at 29 when he took over a Red Sox franchise with a similar sad history in 2002.

Last week, on the verge of having Epstein agree to a five-year $20 million contract, the Cubs announced that bleacher seat prices at Wrigley for next season will be reduced by more than 10 percent for individual games and more than 14 percent for season ticket holders. However, the team moved up the renewal date for season seats to November 16, about a month earlier than usual, and this year the Cubs are requiring a 10 percent deposit.

“We already took a loss of about 37 percent on our Cubs tickets last year [at Gold Coast],” Waisvisz said. “Bleacher tickets are way overpriced at Wrigley to start with.”

With tiered pricing (different pricing for different games), the most expensive bleacher ticket will have a face value of $78, while the least expensive will be just $17. A poor start coupled with poor April weather hurt bleacher sales in 2011. The Cubs had the third-highest average ticket price ($46.90) in baseball in 2011, according to Team Marketing Report.

“You can get a White Sox ticket for less than half of a Cubs ticket, and they put a better team out there. That’s where people are going to go,” Waisvisz said of the two Chicago teams.

Waisvisz added, “We do well with the rooftop tickets,” which are located across the street from the ballpark and overlook Wrigley. “You get food and drinks thrown in.” (Though these tickets are not sold by the Cubs, the team gets a 17 percent share of initial private rooftop ticket sales.)

So while he helped bounce the Bambino, Epstein may find it’s a long way from billy goat to hero in Chicago.

“I think you get a big buzz with a big player,” Waisvisz said, “not a manager or general manager.”