With so much money in town, charity has become as much a high-stakes game as anything that Jacobs and Kraft might have to deal with. A nonstop in-season schedule of fundraisers—giant affairs held at the historic Breakers Hotel or Mar-a-Lago ballrooms, as well as more intimate (relatively speaking) parties at the Everglades club or in private homes—support a wide range of charitable groups, many centered on Boston concerns. These include the Dana-Farber Cancer Institute, Brigham and Women’s Hospital, Schepens Eye Research Institute, and the American Ireland Fund, along with such local mainstays as the American Red Cross, the Norton Museum of Art, and the BCRF. In addition, many Bostonians have their own foundations, funding initiatives in health care, veterans affairs, education, and a host of other causes.

  Socialite C.Z. Guest, poolside, with poodle

All this activity has made for a curious paradox: The rich and successful who head to Palm Beach for some rarefied R&R get caught up in a philanthropic whirl as feverish as anything they might encounter at home. When charity events become the major source of high-society entertainment, being asked to chair or host a fundraiser shows you’ve arrived. “It means you are likely to bring in friends with deep pockets,” which itself is a mark of success, as one observer put it. “And if you agree to host something in your home, you’d better be prepared to show it off, because the photographers are going to be everywhere. Palm Beachers live and die by the shiny sheet.” Friendships have reportedly been fractured over chair appointments, and the planning of table seatings at these elaborate and sometimes competitive affairs requires a diplomat’s nimbleness. The increasing number of year-rounders, who have a vested interest in staying in the spotlight, has only upped the social ante.

To be fair, socializing and consumption in Palm Beach have always been fairly conspicuous, thanks to a winter crowd that was once heavy with such names as Rockefeller, Vanderbilt, and Whitney. And however proper they may have appeared back home, Boston’s Brahmins seemed to find that the Palm Beach sun fermented their spirits substantially. Indeed, its early reputation was so louche that the Rev. Endicott Peabody, legendary headmaster of Groton School, repeatedly advised his charges to “avoid that den of iniquity!”

But after all, Palm Beach was built by big money for big money. In the 1870s, Henry Morrison Flagler, one of John D. Rockefeller’s partners in Standard Oil, began wintering in Florida on a doctor’s advice, but found the facilities less than luxurious. By 1888, he had opened his first Florida luxury hotel, the Ponce de Leon; and eight years later, the historic Breakers (known at the time as the Palm Beach Inn) was constructed.

Palm Beach’s other great entrepreneur was a Bostonian, A. M. “Sonny” Sonnabend, whose holdings included the Biltmore Hotel and the Palm Beach Country Club. He would have been right at home among today’s Boston expats: He was a spectacularly successful turnaround specialist, a Harvard College start, and an international squash champion.

In 1908, Frank Crowninshield, member of a “poor but good” branch of the Boston Crowninshields (he was later editor of Vanity Fair), wrote a tongue-in-cheek treatise called Manners for the Metropolis: An Entrance Key to the Fantastic Life of the 400, purportedly aimed at the nouveau riche millionaires of the West. Crowninshield recommended that these self-made men head to Palm Beach, because society there was “not exclusive, but merry, sumptuous, and expensive.” He also suggested they might meet “many smart men in the gambling rooms.”

Journalist Cleveland Amory, also a member of a Brahmin family, skewered the pretenses of Palm Beach society for Life magazine in 1952. According to Amory, Harry K. Thaw, the coal heir who famously murdered his wife’s lover, Stanford White, in the “girl in the red velvet swing” affair, was dumbstruck upon first seeing Mar-a-Lago. “My God,” he is supposed to have exhaled. “I shot the wrong architect.”

Although most old-line Brahmins were Protestant, the money and influence of the Irish Catholic Kennedys put a crack in the town’s WASP wall. Joseph Kennedy bought his Palm Beach estate in 1933, and it became famous not only as the place where JFK’s presidential run was plotted, but as the “winter White House” and the frequent gathering place of the clan. Last year Kathleen Kennedy told the Palm Beach Daily News how her mother, Ethel, used to take her and her brothers and sisters out of school for two to three months and bring them to the resort.