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Inside Operation Trump, the Most Unorthodox Campaign in Political History

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Gabriel Sherman | NY Mag

On the afternoon of March 15, as voters across five states streamed to the polls, Donald Trump’s campaign advisers gathered by the pool at Mar-a-Lago, the billionaire’s private club in Palm Beach. Hope Hicks, Trump’s 27-year-old press secretary, wearing a cover-up over bikini bottoms, her hair still wet from the pool, scanned headlines on her iPhone next to Trump’s square-jawed campaign manager, Corey Lewandowski. That morning, Politico had reported that Trump allies wanted Lewandowski to be fired for roughly grabbing a female reporter while she tried to ask Trump a question at a press conference (an incident for which he has since been charged with battery). Lewandowski didn’t appear to be worried about his job. He was kicking back in a Trump-brand golf shirt, drinking a 16-ounce Monster energy drink, and chatting with deputy campaign manager Michael Glassner, a former Bob Dole adviser, who at age 52 has been seen as the campaign’s grown-up. Dan Scavino, who first earned Trump’s trust as his golf caddie at the Briar Hall club in Westchester and now handles the campaign’s social media, sauntered over in baggy mesh shorts and a baseball cap. “We go to bed and we’re winning, and we wake up and we’re winning!” Scavino said with a cocky smile.

There is perhaps no better representation of the singularity of the Trump campaign than this handful of political outsiders lounging poolside. They fit no one’s description of a dream team. Hardly any of Trump’s staffers arrived at their positions with high-level political experience. The last time Lewandowski ran a campaign was in 2002, when he managed a losing Senate reelection bid in New Hampshire. Hicks and Scavino spent zero time in politics before this. Hicks did PR for Ivanka Trump’s fashion line and promoted Trump resorts. Scavino graduated from caddying to serve as general manager at Trump National Golf Club; he spent his free time as an unpaid disc jockey at a local radio station. Trump’s national spokeswoman, Katrina Pierson, is a onetime Obama supporter turned tea-party activist who once was arrested for shoplifting. His foreign-policy advisers include a former banker who writes a foreign-policy blog that quotes Kanye West and Oprah, and an energy consultant whose LinkedIn page cites as a foreign-policy credential being one of five finalists for a model-U.N. summit.

“I would take capable over experienced all day long,” Trump said. “Experience is good, but capable is much more important.”

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