Bernard L. Madoff, who died April 14 at 82, was the mastermind of perhaps the largest Ponzi scheme in history, a reviled symbol of Wall Street greed and, once, one of the most sought-after stockbrokers in high finance.

For years, “Bernie” Madoff was regarded as an investment sage. He had clients, homes and boats strewn about exclusive enclaves around the world. Leveraging the clout he had amassed as a legitimate trader, he lured — and eventually fleeced — thousands of investors who entrusted to him their retirement savings, their children’s college funds and their financial security.

His clients included Holocaust survivor and Nobel laureate Elie Wiesel, filmmaker Steven Spielberg, actors Kevin Bacon and Kyra Sedgwick, U.S. Sen. Frank R. Lautenberg (D-N.J.), and scores of retirees and other private individuals. Banks, hedge funds, universities and charities came to rely on his improbably reliable reported returns.

In reality, there were no such returns. For at least 16 years, and perhaps longer, Mr. Madoff ran a scam in which he paid existing investors with money from new clients.

In 2008, as a financial crisis crippled the U.S. economy, investors began seeking withdrawals of funds that Mr. Madoff did not have. His undoing recalled the downfalls dramatized in Greek tragedies: It was swift, excruciating and, in retrospect, inevitable.

On Dec. 10, 2008, Mr. Madoff informed his sons, Mark and Andrew Madoff, that his business, the family’s extravagant wealth and his investors’ flourishing portfolios were “all just one big lie.” The brothers turned their father in to authorities.

His arrest the next day at his New York penthouse stunned many of the most experienced financial experts. Government regulators, too, seemed caught unawares — a perception that fueled public outrage as estimates of victim losses reached $20 billion in actual original investments and $65 billion in recorded paper wealth.

His exposure triggered years-long efforts by officials — notably Irving H. Picard, the court-appointed trustee for the liquidation of Mr. Madoff’s securities firm — to unravel his scheme and compensate victims. Many investors would recoup only a fraction of the money they had given him.

For Mr. Madoff, the personal fallout was catastrophic. His family largely disintegrated. He was so widely despised for his perceived hubris that, reporting for at least one court appearance, he wore a bulletproof vest.

“I live in a tormented state now knowing of all the pain and suffering that I have created,” he said in June 2009, when he was sentenced to 150 years in prison after pleading guilty to 11 felony charges, including securities fraud and money laundering. “I have left a legacy of shame.”

Mr. Madoff reportedly had a heart attack in prison in 2013. In February 2020, he asked a judge for compassionate release, citing end-stage renal disease and other ailments that had left him in need of a wheelchair and constant care. The request was denied.

His death, at a federal prison medical facility in Butner, N.C., was announced by a Bureau of Prisons spokeswoman. The spokeswoman, Kristie Breshears, did not provide a cause but said Mr. Madoff had tested negative for the coronavirus.

At the time of his death, Mr. Madoff remained a chief villain in the narrative of the 2008 economic meltdown that, ironically, had helped unveil his wrongdoing. His scheme did not feature subprime loans, credit-default swaps or the other complex financial maneuvers that had contributed to the onset of the recession. Mr. Madoff had engaged in the simple, ancient act of swindling.

Creation of a myth

To many clients, Mr. Madoff seemed unimpeachable, an entrepreneur whose grit and ingenuity had fueled his rise from relative rags to extreme riches.

In his early working years, he was a lifeguard and installed sprinkler systems, squirreling away his earnings with the goal of starting a private investment firm. He was in his early 20s when he opened Bernard L. Madoff Investment Securities in 1960.

Mr. Madoff was credited with understanding before many others the potential role of the computer in stock-trading. Through innovative use of technology, he made trading faster and more transparent and helped small investors break into circles that for generations had been dominated by floor traders.

In the early 1990s, Mr. Madoff was appointed chairman of the Nasdaq, the first electronic stock market. His firm became an institution and operated from Manhattan’s Lipstick Building, a landmark in the financial capital of the United States.

As his success grew, Mr. Madoff became increasingly fawned on and, by his design, elusive — so that no one would detect the fraudulent operation that, at some point, he began running on the side. Mr. Madoff dated his scheme to 1992, while government investigators traced its beginning to the 1980s. Other accounts suggested that it started even earlier.

Mr. Madoff did not advertise. Rather than lassoing prospective investors, he turned many away. He had discerned that the fewer clients he accepted, the more desirable his services would appear.

There “was a myth that he created around him that everything was so special, so unique, that it had to be secret,” Wiesel, whose Elie Wiesel Foundation for Humanity lost $15 million, said in public remarks.

Former employees recalled the militaristic authority Mr. Madoff exerted over his office. Workspaces were to be kept spotlessly clean. The decor, on his order, featured black and gray tones described by one visitor as “icily cold modern.”

At the same time, Mr. Madoff sought to project authenticity, emphasizing the family-run nature of his business, which included his sons, his brother, Peter B. Madoff, and other relatives. Mr. Madoff adopted a reassuring motto: “The owner’s name is on the door.”

He promised his investors annual returns of about 12 percent — sizable enough to be impressive but modest enough to avoid suspicion. More than large, the returns were steady. Mr. Madoff became widely known as “the Jewish T-bill,” a reference to his Jewish background, his many Jewish clients and an old moniker for conservative government Treasury bonds.

For years, Mr. Madoff rebuffed investors, journalists and government regulators who questioned his results. “It’s a proprietary strategy,” he said in 2001 to Erin E. Arvedlund, then writing for Barron’s magazine and later a Madoff biographer. “I can’t go into it in great detail.”

In retrospect, many experts agreed that the consistency of his returns in a volatile market should have engendered greater skepticism.

Other red flags included the outdated computing system that Mr. Madoff used for his record-keeping and steadfastly refused to replace. His trading statements, produced on a typewriter-ribbon printer in an era of laser machines, looked rather phony in hindsight, at least one investor observed.

In November 2005, Harry Markopolos, a derivatives expert and investment manager, submitted to the Securities and Exchange Commission a memo about Mr. Madoff titled “The World’s Largest Hedge Fund Is a Fraud.” The SEC investigated Mr. Madoff’s firm at least five times before his arrest. But the scheme went on.

In prison, during an investigation by the SEC’s inspector general, Mr. Madoff said that he was “astonished” that regulators had not more fully verified the trading he reported. He said he knew that he would one day be exposed.

“As I engaged in my fraud, I knew what I was doing was wrong, indeed criminal,” Mr. Madoff said at the time of his guilty plea. “When I began the Ponzi scheme, I believed it would end shortly and I would be able to extricate myself and my clients from the scheme. However, this proved difficult, and ultimately impossible, and as the years went by, I realized that my arrest and this day would inevitably come.”

Success, wealth, ruin

Bernard Lawrence Madoff, one of three children, was born April 29, 1938, in New York City. Detailed information about his family was not widely available. His father, Ralph Madoff, wrote on his marriage license that his occupation was “credit.” A family acquaintance recalled that he was perhaps a stockbroker or an account representative, Fortune magazine reported. Both he and his wife, the former Sylvia Muntner, appeared to have had tax and other legal problems involving their finances.

Bernard Madoff attended the University of Alabama before transferring to Hofstra University on Long Island, where he received a bachelor’s degree in political science in 1960. A year earlier, he married Ruth Alpern, his childhood sweetheart. He attended but did not graduate from Brooklyn Law School, having thrown himself into his investment business.

Besides his innovations in computerized trading, he helped develop and popularize a concept known as payment for order flow, in which brokers are paid a penny or more per share for routing business to market makers such as Mr. Madoff’s firm. By the 1990s, the practice had become common, and highly controversial. Critics described the payments as kickbacks.

“People would like to apply pejorative-type terms,” Mr. Madoff said at the time. “I think people that use that kind of terminology are unhappy they are losing business.”

The practice, which is not illegal, continues to be widespread and helped Mr. Madoff make his fortune. Besides his penthouse apartment in Manhattan, his assets included homes in the Long Island community of Montauk and in Palm Beach, Fla., yachts, and shares in private jets.

He also collected watches. He had at least two wedding rings, the New York Times reported, so that he could match the metal of the ring to the timepiece, gold or platinum, that he had selected for wear.

In addition to his business interests, Mr. Madoff operated with his wife the multimillion Madoff Family Foundation that gave money to medical, cultural, educational and other causes. When he confessed his crime to his wife, she was said to have replied with a question: “What’s a Ponzi scheme?”

Ruth Madoff said publicly that she and her husband attempted suicide by taking sleeping pills on Christmas Eve in 2008, when he was under house arrest. Eventually, she said, she ended communication with her husband.

Their son Mark Madoff hanged himself in 2010, on the second anniversary of his father’s arrest, amid lawsuits seeking recovery of Madoff family assets to repay victims of the fraud. Before an earlier suicide attempt, his widow wrote in a book, Mark Madoff left a letter to his father. It read in part: “Bernie: Now you know how you have destroyed the lives of your sons by your life of deceit.”

In 2012, Peter Madoff, who had been chief compliance officer at Bernard L. Madoff Investment Securities, was sentenced to a decade in prison after pleading guilty to charges related to the avoidance of taxes and false filings to regulators. He maintained that he had not been aware of his brother’s Ponzi scheme until shortly before it was revealed to the public. He was released from home confinement in 2020.

In 2014, Mr. Madoff’s son Andrew died of mantle cell lymphoma. A complete list of survivors was not immediately available.

In the years since his arrest, biographers have set out to uncover some tragic flaw that Mr. Madoff possessed, some hardship he had undergone or some pathology that might be diagnosed to explain why he did what he did.

The efforts to fully understand his crime were inconclusive. In email exchanges with Diana B. Henriques, a reporter who covered his downfall in the Times and later wrote a book about him, he cast blame on unsavory clients who, he said, had pushed him into losses that he could not withstand.

Reversing the usual description of his relationship with his investors, he claimed that it was he who had “foolishly trusted” them.

At his sentencing, the judge described the fraud as “extraordinarily evil” and recounted a scene in which Mr. Madoff assured a grieving widow that her money was safe with him.

“I’m sorry,” the defendant said before the courtroom.

He added, “I know that doesn’t help you.”

Matt Zapotosky and former Washington Post writer Tomoeh Murakami Tse contributed to this report.