On Thursday night, Uber CEO Travis Kalanick got a rare chance to play the good guy when he was honored by the Iraq and Afghanistan Veterans of America for his work on behalf of veterans. 

A day later, Kalanick was back in his more familiar role as provocateur and pugilist par excellence. At a dinner he hosted in Manhattan Friday night for members of the New York media elite, one of his top executives, senior vice president of business Emil Michael, suggested that the company should devote a fraction of its multi-billion-dollar war chest to digging up dirt on critical journalists in order to smear and discredit them.

According to Buzzfeed, which reported Michael's remarks, he enthusiastically described how $1 million dollars -- a pittance to a company reportedly valued at more than $20 billion -- could be used to hire four investigative reporters and four "oppo" researchers of the sort used by political campaigns. The muckrakers would focus their efforts on targets like Pando Daily editor in chief Sarah Lacy, who recently declared she had stopped using Uber in protest of its stances toward women and user safety.

The Buzzfeed report also claimed that another Uber official accessed the profile of Buzzfeed reporter Johana Bhuiyan in contravention of the company's privacy policies. 

Michael was quick to apologize, although he didn't pass up the chance to get in one more dig at the Sarah Lacys of the world:

The remarks attributed to me at a private dinner -- borne out of frustration during an informal debate over what I feel is sensationalistic media coverage of the company I am proud to work for -- do not reflect my actual views and have no relation to the company's views or approach. They were wrong no matter the circumstance and I regret them.

As for the violation of Bhuiyan's profile, Uber says it has safeguards in place to prevent misuse of users' account data. But it's not the first time the company has been accused of taking advantage of its visibility into users' movements. Earlier this year, venture capitalist Peter Sims announced that he had quit using Uber after learning that his whereabouts had been projected onto a screen at a party as a demonstration of Uber's so-called "God view."

The idea of angering journalists or VCs isn't the kind of thing that would cause much soul-searching for Kalanick, who pursues a strategy of what he calls "principled confrontation" with the powers that be, from taxi drivers unions to city councils. 

The danger for Uber is that, in picking fights with what he views as elite cliques, he ends up alienating the masses. It's not only reporters who worry about their privacy. In a recent Pew survey, 91 percent of respondents expressed concern about how companies use their personal information. If Uber squanders its users trust pursuing petty vendettas, it won't be able to buy it back, no matter how much capital it raises.