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“I wouldn’t call it conversation,” Gelb said. “It’s this sort of breathless monologue that you can only engage by interrupting. Dick is an advocate. He almost always has a case to make.” Holbrooke’s forcefulness is tempered by an endearing vulnerability—the nakedness of his ambitions and pleasures and insecurities. He takes pains arranging the seating chart for official dinners. Between government jobs, he worked as an investment banker, and, according to USA Today, he’s worth at least seventeen million dollars, but he still looks as if he’d dressed in a hurry. He reads voraciously, writes quickly and well, and consumes large quantities of schlock entertainment. (Holbrooke is especially fond of “There’s Something About Mary.”) His great advantage over most colleagues and opponents is his analytic and synthetic prowess, which allows him, for example, to break down the reasons for the Taliban’s successful propaganda campaign in the tribal areas while connecting it to imperial British history in the region. As for his flaws, he seems remarkably unaware of them. Holbrooke cannot be kidded about the trait for which he’s best known: his ego.

—from “The Last Mission,” George Packer’s Sept 2009 New Yorker profile of Richard Holbrooke. Photograph by Brigitte Lacombe.