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Well, I don't know about the "first of the generation" thing, but maybe the first that doctor had seen. You get vaccinated as an infant, but the vaccine wears off.
According to the NYTimes, there were 18,957 reported cases of pertussis in the United States in 2004, up from 9,784 in 2003. The CDC says in the US, 5000-7000 cases are reported each year.
First in a generation??? WTF? I see people with whooping cough all the time at the lab. It's usually a pretty nasty cough, very chesty and barky sounding. If your roommate does indeed have whooping cough, the doctor should be keelhauled for sending him out in the world like that. It's VERY contagious and can be fatal. I don't know about your area, but here we are required to report any positive results to the state. if you have any symptoms seek help immediately! It's a simple nasopharangeal swab culture to test for it.