Well, it's possible that a Villanova alum could win a medal for the first time since the 2000 Sydney Olympics: her name is Dotsie Bausch (Dotsie Cowden when she was at VU). Prior to today, I had no idea that Bausch existed, let alone that she was a 1995 Villanova graduate who is about to compete at her first Olympics in track cycling at the age of 39. A latecomer to the sport, Bausch began as a hobby rider at 26, and now, 13 years later, she's an Olympian. That's absolutely incredible. She's also a survivor, whose story of conquering her demons and becoming an Olympian should make you proud to be an American, as well as a Villanovan.
Note: The fact that Dotsie Bausch is on the US Olympic Team makes her the only Villanovan on Team USA in 2012, the first Villanovan I can think of who didn't play a varsity sport that made the Olympics, Villanova's first cycling Olympian and means that there has been an American on Team USA in every single Olympics since the 1948 London Games (USA boycotted the 1980 Moscow Games, but Don Paige and Mark Belger were on the team).