PALM BEACH, Fla. — In this exclusive, image-conscious retreat where enormous hedges encircle grand mansions and valets park cars at the supermarket, wealthy residents pay vast sums to shield their private lives from view, even as they crave to be seen at the charitable events and black-tie galas that go on almost daily from November to May, a glittering time known as “the season.”

The messier reality is that the history of this 18-mile barrier island, a playground for the rich for more than a century, is littered with stories of American aristocrats who failed to stay out of the local tabloids. Wall Street barons ran off with maids, star-studded couples scandalously divorced and, not surprisingly, high-priced escorts worked the upscale bars and hotels.

The latest scandalous episode spilled into public view last week when Robert K. Kraft, the owner of the Super Bowl champion New England Patriots and a fixture in this haven of billionaires and millionaires, was charged with two first-degree misdemeanor counts of soliciting a prostitute at a massage parlor in the town of Jupiter, a 30-minute drive away. There, the police said they twice caught Mr. Kraft, 77, on video paying for sex with a woman.

Mr. Kraft has denied the charges. But even the suggestion that a prominent sportsman, businessman and philanthropist might have sought company in a seedy massage parlor up the road has many residents wondering why a man worth an estimated $6.6 billion would risk his reputation so recklessly on a $79-an-hour massage.