His classmates recall him as a bright, focused student with a forceful personality. Mark Rotenberg, who lived a floor below him in their fraternity house, remembers Sherman once yelling down from his upstairs window, “Hey, Rotenberg, why are you so ugly?”

“He was a real New Yorker,” Rotenberg says, “very opinionated.”

Eager to begin working, Sherman interviewed with Big Eight accounting firms during his senior year. “I wanted to get started. I didn’t know you were supposed to go to Europe for six months and hack around,” he says. He accepted an offer from Arthur Young for $9,500 a year, married a girl he attended high school with, and settled into a $219-a-month apartment in Flushing, Queens. Then came the birth of their first daughter; a new house in Kings Park, on Long Island’s North Shore; daily commutes to and from Manhattan; and night classes toward an M.B.A. at Baruch College.

At 29, Sherman got a life-changing call from a headhunter representing Miles Collier, the then-30-year-old grandson of advertising tycoon and industrialist Barron Gift Collier. He was looking to recruit a personal financial adviser. Sherman’s middle-class Jewish background contrasted with the Collier heir’s patrician reserve, polished at Yale and Columbia Business School. Still, Collier was impressed with Sherman’s tenacity and firm grasp of finance, and soon he offered Sherman a job. It was 1978, and the two wings of the Collier clan had decided to partition the family’s jointly owned assets, including agricultural land, cattle ranches, and a newspaper, the Naples Daily News. Sherman soon joined the board of the News and later recommended that the Colliers sell the paper. At the time, national newspaper chains were crisscrossing the country buying up family-owned papers. Sherman realized the Colliers could make a killing, and in 1986 he engineered a sale to E.W. Scripps for a record $170 million. It was a surprise, however, to the newsroom.

George Cecil, the News’ editor at the time, recalls a phone call from his publisher summoning him back from vacation. “It was a great shock. The sale was a closely held secret in an industry that doesn’t keep secrets,” Cecil recalls.

It was Miles Collier who staked Bruce Sherman when he was ready to go out on his own. Private Capital Management was founded in 1986 with $50 million from Collier. Today, Sherman manages about $24 billion. While hedge fund managers have become captains of 21st-century commerce sailing the seas of high risk, Sherman trolls the backwaters of finance. Like Warren Buffett, Sherman is known as a value investor, conducting exhaustive research before buying large positions in firms that generate lots of cash—the kind of disposable capital that can reduce debt, fund acquisitions, or repurchase stock. Sherman typically holds positions for three to five years, waiting for their stocks to rise or agitating for a sale, aiming for a hefty gain. In the past nine years, in fact, Buffett’s holding company, Berkshire Hathaway, has acquired three companies from Sherman’s portfolio. Since 2003, 42 other companies in Sherman’s portfolio have been sold to new owners, including Harrah’s Entertainment, which went to private equity giants Apollo Management and Texas Pacific Group for $17.1 billion in 2006.

Sherman’s big years came between 1999 and 2004, when assets under his management exploded from $4.4 billion to a high of $31 billion. (He sold P.C.M. in 2001 to Legg Mason, the Baltimore-based financial institution, for $1.4 billion but has remained firmly in charge of the portfolio.) Sherman’s long-term track record is impressive: With the help of its president, Gregg Powers, P.C.M. reaped a $1 billion return on Qualcomm, an undervalued telecommunications concern, in the 1990s tech boom. P.C.M.’s returns have averaged close to 20 percent almost every year since its founding. Sherman charges a 1 percent management fee on all assets, spread across more than 5,000 accounts, a company spokesperson said.

His early career exemplifies the instincts and style that built his fortune. In the late 1980s, the Colliers were looking for undervalued properties. In 1988, Sherman found a great target: Local Financial Corp., an Oklahoma bank that had assets of $800 million. He lined up majority owners behind a $26 million offer and marched into the bank to tell Edward Townsend, the bank’s C.E.O., that the Colliers had bought the bank out from under him. “I didn’t want to sell,” Townsend remembers, but Sherman’s stealth attack gave him no room to maneuver. “Bruce is very good at that. He’s the kind of guy who might terribly out-trade you.”