The Chicago Cubs have only the abysmal Minnesota Twins and San Diego Padres to thank for keeping themselves out of the basement of baseball following Tuesday’s 5-3 win over San Diego. Sitting at 17-32 after an encouraging early May start has Theo Epstein and Jed Hoyer sticking to their guns without making any quick-trigger decisions.

But thanks to the worse-than-expected start, the only thing hotter than summer weather in Chicago could be the seat under Epstein’s $15 million bottom.

Two months into the season, one has to wonder, did Epstein really know what he was getting himself into?

Epstein is dealing with the animal that is the Chicago fanbase. It’s been too many years to count since the last World Series for Chicago. Just one World Series in between barely holds the fans over on the South Side.

Chicago Bears fans still have copies of the Superbowl Shuffle stuffed into VCRs in the basement. And Derrick Rose’s torn ACL ruined any chance of a return to the Michael Jordan era for the Bulls.

The Cubs’ struggles this summer come in the midst of one of the most frustrating years in Chicago sports. Patience is thinner than a reincarnated Charles Barkley on Weight Watchers, even though it was supposed to be expected that the Cubs wouldn’t compete for three years.

Epstein has never had to deal with such pressure. Boston doesn’t compare to Chicago, especially when the Red Sox were playoff, and eventually championship, ready upon Epstein’s arrival. The Cubs couldn’t be farther from that case.

The Cubs’ best player, presumably Starlin Castro, would be lucky to be the fourth best offensive weapon on the Red Sox—with a position change required due to the presence of Nomar Garciaparra. 

Manny Ramirez, Johnny Damon and Garciaparra all were waiting for Epstein to build around. Derek Lowe and Pedro Martinez anchored the staff. With the signing of David Ortiz, the Red Sox were set for a run for multiple years.

Epstein’s latest test in Chicago includes Castro, Bryan LaHair and…I’ll stop there. Whoever the third best offensive weapon is may be worse than Lance Armstrong riding his bike in the Indianapolis 500.

Winning a title in his first year gave Epstein plenty of years to get back in 2007. He won’t be blessed with that opportunity here. The Cubs are more than Anthony Rizzo away from a title. Brett Jackson continues to show why he couldn’t win the starting center field job over Tony Campana and career utility infielder Joe Mather.

Expect even more roster turnover next year. This is a challenge Epstein’s never had before. And there’s no emotional attachment to succeed as there was in Boston.

He already has two championships with his dream job in Boston. How motivated is Epstein actually going to be to bring one home to Chicago when doubt begins to creep in 2014? Is he mentally prepared to handle the criticism as the losses mount?

While every other leader has been forced out, Epstein won’t wait for that to happen. One year of criticism for poor signings—John Lackey and Carl Crawford—and a September collapse was enough for Epstein to gladly walk away from his dream job.

Who knows how many losing streaks will mount before he wants to run away from this one.

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