Hillary's Worst Mistake

As pointed out by Josh Green in this month's Atlantic Magazine, and as noted by Kevin Drum:

And as a newcomer to national politics, [Obama] needed to establish credibility by making inroads to major donors — most of whom, in California as elsewhere, had been locked down by the Clinton campaign.

Silicon Valley was a notable exception. The Internet was still in its infancy when Bill Clinton last ran for president, in 1996, and most of the immense fortunes had not yet come into being; the emerging tech class had not yet taken shape. So, unlike the magnates in California real estate (Walter Shorenstein), apparel (Esprit founder Susie Tompkins Buell), and entertainment (name your Hollywood celeb), who all had long-established loyalty to the Clintons, the tech community was up for grabs in 2007. In a colossal error of judgment, the Clinton campaign never made a serious approach, assuming that Obama would fade and that lack of money and cutting-edge technology couldn't possibly factor into what was expected to be an easy race. Some of her staff tried to arrange "prospect meetings" in Silicon Valley, but they were overruled. "There was massive frustration about not being able to go out there and recruit people," a Clinton consultant told me last year. As a result, the wealthiest region of the wealthiest state in the nation was left to Barack Obama.

Furthermore, in Silicon Valley's unique reckoning, what everyone else considered to be Obama's major shortcomings — his youth, his inexperience — here counted as prime assets.