The individual who seems to have lost most in the collapse of Bernard Madoff's $50 billion fraudulent financial empire is a 95-year-old Boston philanthropist, Carl Shapiro.

Mr Shapiro has been a personal friend of Mr Madoff for more than 50 years, and had entrusted much of his fortune and nearly half of the assets of his charitable foundation to the shamed New York investor. More than half a billion dollars is missing, according to a family spokesman.

The revelation that the money has disappeared into what Mr Madoff has described as a "giant Ponzi (pyramid selling) scheme" is a personal betrayal for Mr Shapiro, who was so close to the financier that he has frequently been described as one of his "go-to" men, credited with setting up meetings with other potential Madoff investors in the blue-blooded golf clubs in New York and Florida to which both men belonged.

Introductions were said to have been made in the hallowed and exclusive premises of the $250,000-a-year Palm Beach Country Club in Florida, the venerable Old Oaks golf club in wealthy Westchester County, New York, in the Atlantic golf club in the Hamptons, and at the Boca Rio golf club in Boca Raton, Florida, an area filled with immensely rich retired people.

Such was former Nasdaq chairman Mr Madoff's reputation as a safe pair of hands with other people's fortunes, would-be investors were said to spend years trying to get onto the client list of Bernard L Madoff Securities, spending hundreds of thousands of dollars on membership fees for the clubs he frequented just for the chance of meeting him.

The minimum starting investment was a million dollars, and Mr Madoff's mystique only grew because he turned down many of the people so eager to invest with him.

There is no suggestion that Mr Shapiro had any inkling of the alleged financial irregularities that Mr Madoff admitted to his two sons last week, leading to his arrest on fraud charges last Thursday. According to the Boston Globe, the Carl & Ruth Shapiro Family Foundation has lost about $145 million.

Carey O'Donnell, a spokeswoman for the Shapiros, has told the Wall St Journal that the couple had at least an additional $400 million of their personal fortune invested with Mr Madoff. Analysts say that it could represent up to half their wealth.

"All I can say is that this is an awful, awful time for us," Ruth Shapiro told a reporter from The New York Times over the weekend.

Mr Shapiro made his fortune making women's clothes under the brand Kay Windsor Inc, which he set up in 1939. When he sold the business to Vanity Fair Corp in 1971 it was one of the largest clothing manufacturers in America. Introduced to Mr Madoff by Robert Jaffe, his son-in-law, Mr Shapiro was among the original investors in Mr Madoff's company when it launched in 1960.

Mr Shapiro and his wife set up their charitable foundation the following year, in 1961, and over the decades have been big donors to the Boston Museum of Fine Arts, the Boston Symphony Orchestra, Brandeis University in Boston which Mr Madoff also supported through his own charitable foundation, the Beth Israel Deaconess Medical Center and the Brigham and Women's Hospital where the Carl J. and Ruth Shapiro Cardiovascular Center opened this spring.

Building work is due to start next week at Boston Medical Center on the Shapiro Ambulatory Care Center, a nine-floor, $135 million facility paid for in part with $15 million from the family foundation, according to the New York Times.

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