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invariably greeted each other with a kiss and that the adult Jared called his father Daddy. Neither Donald nor Jared, no matter their domineering fathers, went into the world with humility. Insecurity was soothed by entitlement. Both out-of-towners who were eager to prove themselves or lay rightful claim in Manhattan (Kushner from New Jersey, Trump from Queens), they were largely seen as overweening, smug, and arrogant. Each cultivated a smooth affect, which could appear more comical than graceful. Neither, by choice nor awareness, could seem to escape his privilege. “Some people who are very privileged are aware of it and put it away; Kushner not only seemed in every gesture and word to emphasize his privilege, but also not to be aware of it,” said one New York media executive who dealt with Kushner. Both men were never out of their circle of privilege. The main challenge they set for themselves was to enter further into the privileged circle. Social climbing was their work. Jared’s focus was often on older men. Rupert Murdoch spent a surprising amount of time with Jared, who sought advice from the older media mogul about the media business —which the young man was determined to break into. Kushner paid long court to Ronald Perelman, the billionaire financier and takeover artist, who later would host Jared and Ivanka in his private shul on Jewish high holy days. And, of course, Kushner wooed Trump himself, who became a fan of the young man and was uncharacteristically tolerant about his daughter’s conversion to Orthodox Judaism when that became a necessary next step toward marriage. Likewise, Trump as a young man had carefully cultivated a set of older mentors, including Roy Cohn, the flamboyant lawyer and fixer who had served as right-hand man to the red-baiting Senator Joe McCarthy. And then there was the harsh fact that the world of Manhattan and particular its living voice, the media, seemed to cruelly reject them. The media long ago turned on Donald Trump as a wannabe and lightweight, and wrote him off for that ultimate sin—anyway, the ultimate sin in media terms—of trying to curry favor with the media too much. His fame, such as it was, was actually reverse fame—he was famous for being infamous. It was joke fame. To understand the media snub, and its many levels of irony, there is no better place to look than the New York Observer, the Manhattan media and society weekly that Kushner bought in 2006 for $10 million—by almost every estimate $10 million more than it was worth. 1 OK Ok The New York Observer was, when it launched in 1987, a rich man’s fancy, as much failed media often is. It was a bland weekly chronicle of the Upper East Side, New York’s wealthiest neighborhood. Its conceit was to treat this neighborhood like a small town. But nobody took any notice. Its frustrated patron, Arthur Carter, who made his money in the first generation of Wall Street consolidations, was introduced to Graydon Carter (no HOUSE_OVERSIGHT_019939