Henry Gomez was a public relations executive at cable's Home Box Office network when he called eBay in 1999, thinking "it might be cool to sell some Sopranos stuff" on the "hot new auction site."
Early in their discussions, Jennifer Caukin, the woman at eBay with whom he worked on the promotion, mentioned the company was hiring a communications director and invited him to apply.
Gomez met Meg Whitman, then eBay's CEO, for dinner in Boston in February 2000, and he went to work for her the next month. A decade later, he is the closest adviser to the Republican nominee in her gubernatorial campaign.
He is in many ways an unlikely fit for the job. He has limited political experience and is a Democrat.
Despite speculation he could be destined for a high-ranking appointment within a Whitman administration, he professes no interest in working in Sacramento.
"I'm not doing anything in Sacramento," Gomez said. "I'm heading home after the campaign."
In mid-September, at the San Francisco offices of the online review site Yelp, Gomez paced between the ping pong and pool tables at one end of a sprawling lounge, and the stage on the other end, where Whitman addressed a young and skeptical crowd. He wore blue jeans and a blazer, his arms folded in front of him and his shirt two buttons undone.
"It was a good solid day," he said later, over coffee at a cafe off Mission Street.
One reason Gomez is valuable to Whitman and her political consultants it that he, more than anyone else, tells her when it's not a good day.
Gomez, 47, oversees Whitman's speech writing and press operations and represents the candidate in internal strategy talks. He was with her when she met Jeff Randle, the first consultant she hired. He situated the campaign office in Cupertino, and he assembled the rest of her team.
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