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Minute 14:59

By Rachelle Bowden in News on Jul 21, 2005 8:10PM

2005_07_payton_rancic_point.jpgChicagoist's best friend in New York used to room with Alex Michael from the first season of The Bachelor. Aside from being really arrogant and self-centered, Alex spent every waking moment riding out his 15 minutes of reality TV fame. Calling girls on their birthday, making special appearances, etc. And since we like never hear of Bill Rancic actually working on the Trump Tower, but always hear about him doing promos and charity events, we're guessing that's what his deal is too.

So, you were wondering what exactly Bill's been doing these days? Not really? Well, we're going to tell you anyway. Or at least what he was doing last night. In what seems to be the most random matchup ever, Bill played a game of Monopoly against Connie Payton, Walter Payton's widow. Despite Bill's so called "real estate experience", he lost!

The event took place at a Lincoln Park opening of a Bank of America branch and raised $5,000 for the Walter and Connie Payton Foundation, a charity that benefits neglected, abused and underprivileged children. Hey, maybe they could buy some homeless Chicago students some school supplies!

A reader sent us these photos of the event, there's more after the jump -