Prescott Bush, the father and grandfather of future Presidents, was the eight-time club champion on the golf course at the Round Hill Club, one of eight country clubs in Greenwich, Connecticut. Bush was a staunch believer in standards; he required his sons to wear a jacket and tie for dinner at home. He was tall, restrained, and prone to righteousness; friends called him a “Ten Commandments man.” In the locker room at Round Hill, someone once told an off-color joke in front of his fourteen-year-old son, George H. W. Bush, and Prescott stormed out, saying, “I don’t ever want to hear that kind of language in here again.”
In Greenwich, which had an unusually high number of powerful citizens, even by the standards of New York suburbs, Prescott Bush cast a large shadow; he was an investment banker, the moderator of the town council, and, from 1952 to 1963, a United States senator. In Washington, he was President Eisenhower’s golf partner, and the embodiment of what Ike called “modern Republicanism.” Prescott wanted government lean and efficient, but, like Nelson Rockefeller, the New York governor whose centrism inspired the label Rockefeller Republican, he was more liberal than his party on civil rights, birth control, and welfare. He denounced his fellow-Republican Joseph McCarthy for creating “dangerous divisions among the American people” and for demanding that Congress follow him “blindly, not daring to express any doubts or disagreements.” Bush could be ludicrously aristocratic—he had his grandchildren call him Senator—but he believed, fundamentally, in the duty of government to help people who did not enjoy his considerable advantages. He supported increasing the federal minimum wage and immigration quotas, and he beseeched fellow-senators, for the sake of science, education, and defense, to “have the courage to raise the required revenues by approving whatever levels of taxation may be necessary.”
Long after Bush died, in 1972, his family stayed central to the community of Greenwich Republicans. His son Prescott, Jr., known as Pressy, served as the chairman of the Republican Town Committee; alumni of the Bush Administrations still live around town. Each year, the highest honor bestowed by the Connecticut Republican Party is the Prescott Bush Award.
When Donald Trump ran for President, he was hardly a natural heir to the Greenwich Republican tradition. In the eighties, he bought a mansion on the town’s waterfront, but he did not often observe the prim Yankee ethic inscribed on the Greenwich coat of arms: fortitudine et frugalitate—courage and thrift. Locals were embarrassed by the house’s gilded décor, and, after he and his wife Ivana divorced, she sold it. When George H. W. Bush called for a “kinder, gentler nation,” Trump responded, “If this country gets any kinder or gentler, it’s literally going to cease to exist.” In early 2016, even before Trump was asserting his right to “locker-room talk,” he was denounced in Greenwich Time, the town’s daily newspaper, by Leora Levy, a prominent local fund-raiser. “He is vulgar, ill-mannered and disparages those whom he cannot intimidate,” she wrote. Levy—the latest winner of the Prescott Bush Award—was lending her support to Prescott’s grandson Jeb Bush, the former governor of Florida.
But not everyone in Greenwich was excited about Jeb. Jim Campbell was the chairman of the Republican Town Committee. The Campbells, like the Bushes, had deep roots in town. Jim prepped at Exeter and graduated from Harvard and Harvard Law School, before working in Europe and returning home as a real-estate executive. On a fall evening, Campbell attended a reception for Jeb Bush at the Belle Haven Club, a private tennis-and-boating club overlooking Long Island Sound. Jeb was expansive and mild, which struck Campbell as precisely wrong for the political moment: “He gave a whole talk about a woman named Juanita in South Florida, and how ‘immigration is love,’ and I just looked at the people I came with and said, ‘Does he think he’s already the nominee? He’s running in a tough Republican primary, and just because we’re at the Belle Haven Club doesn’t mean we’re all voting for him.’ ”
At home one night, watching television, Campbell happened on a Trump rally in Iowa. “I’m not a hard-core conservative—I’m a Republican from Greenwich,” Campbell said. “But I listened, and he had that line that he would use: ‘Folks, we either have a country or we don’t.’ And I felt the chill—like Chris Matthews with the little Obama zing up the leg. I’m, like, ‘Oh, my God, this is a really good line.’ ” To Campbell, Trump was describing immigration in ways that resonated: “Could somebody finally say that we’re allowed to enforce the law at the border without being called a racist? I lived in Switzerland for ten years. Do you think I was allowed to go around without a passport?”
Campbell tapped out a text message to a friend: “Trump live - can’t turn the channel. Unbelievable. I don’t think any R can beat him.” Campbell watched the rally for forty-five minutes. “He was mesmerizing,” he said. Not long afterward, he saw a Republican debate in which Trump described the invasion of Iraq as a mistake. For Campbell, the acknowledgment came as a catharsis. “Of course it was a big, fat mistake,” he told himself. “He says everything I think.”
In early 2016, Campbell attended a dinner for Republicans at the Delamar Greenwich Harbor, a Mediterranean-themed boutique hotel that is popular with local finance executives. After a dinner speaker mocked the notion of building a wall and imposing tariffs, Campbell raised his hand: “I said, ‘With all due respect, why is it that we’re not allowed to support a candidate who supports the things that you just ticked off?’ ” Campbell knew that his question would cause a stir, but he had decided that it was time “to let everybody know who I was supporting.” When the event was over, he discovered that he was not alone: “I had four guys make a beeline for me, Wall Streeters, all saying, ‘What can we do? Can I sign up? Are you organizing?’ ”
In February, 2016, with Jeb still vying for the nomination, Campbell endorsed Trump. “I just think there’s a lot of people supporting Donald and don’t want to say so,” he told a local reporter. That spring, as Connecticut Republicans prepared to vote in their primary, political observers predicted that John Kasich, the moderate governor of Ohio, would prevail in towns and cities from Greenwich to Fairfield—a stretch of American bounty known as the Gold Coast. Instead, Trump largely dominated the region.
Four years later, Trump signs are still scarce in Greenwich (population 62,600), but his supporters are easy to find. There is the first selectman—the local equivalent of mayor—and the chairman of the Greenwich finance board, as well as an ardent backer who serves in the state House of Representatives. Some local Republicans helped fund Trump’s Inauguration, and some joined his White House, including Linda McMahon, the former professional-wrestling executive who headed the Small Business Administration, and Hope Hicks, Trump’s longtime communications adviser. (She once captained the Greenwich high-school lacrosse team.) Others in town have abandoned their objections to Trump. Leora Levy, who called him vulgar in the local paper, took to applauding his “leadership” and quoting him on Twitter, where she adopted some of his rhetorical style. “AMERICA WILL NEVER BE A SOCIALIST COUNTRY!!!” she posted. “WE ARE BORN FREE AND WILL STAY FREE!!!” Last fall, Trump nominated her to be the American Ambassador to Chile.