Sherman seems an unlikely provocateur of this unfolding tableau. Noto­riously press shy, he rarely gives interviews, doesn’t have a publicist, and shows no desire to insinuate himself into the media power corridors of Manhattan. “He jokes about the press,” says Sherman’s friend and neighbor Jay Baker, the ­former president of Kohl’s department stores. Though Sherman began reducing his exposure last winter by bailing some clients out of their newspaper positions, he remains the most powerful newspaper investor in the land, managing for clients more than $1.7 billion worth of newspaper stocks—about 9 percent of the New York Times Co., 3 percent of Gannett, and 12 percent of McClatchy.

The morning after his party, however, Sherman did grant an interview. He arrived in tropical attire and eased com­fortably into a leather couch in the wood-paneled bar of the Ritz-Carlton as he sipped decaffeinated coffee from a paper cup. He would soon be off to make his rounds as a trustee of the wine festival, where a charity auction would raise $18 million. He declined to talk about his newspaper investments, save to say, “This business is about judgments.”

In an earlier interview, a spokesman for Private Capital Management offered his assessment of the press sniping over Wall Street’s pressure on publicly traded newspaper conglomerates: Asset managers like Sherman have a fiduciary responsibility to put their clients first, and “these com­panies should have thought of that before they went public.”

When you meet Sherman, it’s clear that Naples’ genteel atmosphere agrees with him. He is a garrulous man with wire-rim eye­glasses, broad shoulders, and a slight paunch. In conversation, he speaks in the friendly, avuncular tone of one who received his break in life and wishes you the same good fortune. He likes to tell stories, his conversation rattling out in brusque, staccato bursts.

“I worked hard,” he says. “I may not have known the answers, but I pride myself on knowing the questions.” Research—80 percent of the game for Sherman—is, he says, “what I love to do.”

Some of his oldest acquaintances marvel at how far he’s come. “Bruce hit his stride later in life,” says Sheindlin, who saw her cousin frequently at family gatherings. “It’s always surprising when someone you knew as a kid grows up to become a man to whom people give millions of dollars to invest and say, ‘We trust you with it.’ ”

Since Sherman felled Knight Ridder, the press has labeled him as reclusive. Actually, he has always operated outside the power orbits of the Ivy League, Wall Street, and the media, and he relishes the freedom that doing business in Naples affords. There, Sherman has carved out his social and financial fiefdom. And it’s some life.

Twice divorced, Sherman finally met a woman of his disposition: Cynthia Kahn, a flaxen-haired media law­yer. They wed in 1999 at the Pierre, in New York City, seven and a half months after Sherman’s second divorce. Kahn, now 51, quit practicing law, and the two wove themselves tightly into Naples’ moneyed fabric of real estate, philanthropy, and politics, becoming major supporters of the Republican Party, Jewish causes, and children’s charities. In 2003, they bought their $9.5 million penthouse at the Regent, a 37-unit high-rise on Gulfshore Boulevard, and commissioned a multimillion-dollar renovation, bringing in Steven Spielberg’s onetime decorator and installing an undulating ceiling crafted from English sycamore.

Bruce Sherman grew up far from wealth. The son of an aeronautical engineer and an elementary school teacher, he was the youngest of three brothers in a 2,400-square-foot house in the Little Neck neighborhood of Queens. Bruce earned average marks at Bayside High School, where he enjoyed his bookkeeping class. He then headed to the University of Rhode Island.

An accounting major, Sherman eschewed 1960s campus politics and joined a fraternity, becoming treasurer. In his freshman year, he took a job servicing the university’s vending machines. It was 1965, and the U.S. Treasury had begun to phase out silver quarters, worth 30 cents, in favor of new ones minted from copper and nickel. Spotting an opportunity, Sherman rifled through the change bins and swapped new quarters for the old.