George Allen

Having a solid standing among the digerati doesn't mean you'll make a great politician. It also doesn't mean you're necessarily all that tech-savvy. Take the example of George Allen, who sat on the board of directors for a handful of high-tech start-ups in his home state of Virginia and was deemed one of the senators most friendly to the tech industry when it came to his political positions.

That, however, didn't prepare Allen for the potential dangers of the Web 2.0 revolution. While running for re-election in 2006 in a tight race against Jim Webb, Allen was videotaped using an obscure racial slur at a campaign rally, and it hit the Internet almost instantly. Allen lost his bid for re-election: The politician who was named CNET News' most tech-friendly senator in our 2006 Technology Voters' Guide, in effect, saw his political career ruined by a YouTube video.