Power Trip

Donald Trump and the Power of Disappointment

He thought the presidency would compensate for his fragile ego. He was very wrong.

Garrett Graff
GEN
Published in
7 min readOct 17, 2018

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Photo by Chip Somodevilla/Getty Images

TThe world was laughing at Donald Trump. He had taken the stage at the United Nations in September and opened with one of his signature Trumpian boasts, bragging that he “has accomplished more than almost any administration in the history of our country.” And the world’s diplomats laughed, their guffaws migrating across the room as the U.S. president’s remarks were translated into the diplomatic corps’ native languages.

It was, to this president, his worst nightmare. Donald Trump has always feared being the punch line — and he’s spent much of his life being the butt of jokes from the elite, the fancy Manhattanites who still see the brash developer as a florid, classless braggart. His presidential run was fueled to some degree by the infamous White House Correspondents’ Dinner in 2011, where President Obama led Washington’s elite in laughter at Trump’s expense, needling his hit TV show, The Apprentice, which had reinvigorated Trump’s stalled business empire and rebranded the bankruptcy king as a business savant. The black tie–clad newsmakers and journalists laughed at Obama’s mere ironic mention of Trump’s “credentials and breadth of experience.”

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Garrett Graff
GEN
Writer for

Journalist and Historian. Director, Aspen Institute Cyber Program, Contributor to WIRED, CNN, and Longreads. Author, "The Threat Matrix" and "Raven Rock."