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Madoff is behind bars and isn’t talking. But a Fortune investigation uncovers secrets of his massive swindle.
The employees were transfixed. Standing on the mid-Manhattan trading floor of tie Bernard L. Madoff Investment Securis in late 2007, a half-dozen staffers stared up at the ceiling-mounted TV as CNBC aired a report on the mysterious Palm Beach death of a hedge fund manager who had been leading a double life. The police, it appeared, were even considering the possibility that he had been murdered. “Bernie,” someone casually asked as Madoff happened to walk by, “have you heard of this guy?”
Madoff glanced at the screen, blanched, and exploded: “Why the fuck would I be interested in some shit like that?” The employees recoiled. “I never saw him react like that before,” says a Madoff trader who witnessed the outburst. “It obviously hit a nerve.”
Then there was the man who ran the floor, Frank DiPascali, Madoff’s chief deputy on 17. He was a 33-year veteran of the firm, with a rough Queens accent and a high-school education, but nobody was quite sure what he did or what his title was. “He was like a ninja,” says a former trader in the legitimate operation upstairs. “Everyone knew he was a big deal, but he was like a shadow.”
There were other mysteries, as we shall see. But even after it detonated five months ago in a fireworks display of betrayal and recrimination, Madoff’s scheme — possibly the biggest investment fraud in the nation’s history — has remained among the hardest to penetrate. Most commonly, white-collar cases begin with a quiet, behind-the-scenes investigation, followed by a series of deals with junior employees, who are squeezed by prosecutors to cough up details about their superiors. Step by step, the prosecutors move up. Finally comes the denouement: the ringmaster hauled into court in handcuffs.
But with Madoff every aspect of that traditional narrative has been inverted. The case began with his flabbergasting confession, which set off the investigation. Madoff claimed he committed his crimes all by himself, but because they spanned decades and continents, a fog of suspicion immediately engulfed Madoff family members who worked at the firm, as well as employees and business associates.
Now that fog may be about to lift. Fortune has learned that Frank DiPascali is trying to negotiate a plea deal with federal prosecutors in which, in exchange for a reduced sentence, he would divulge his encyclopedic knowledge of Madoff’s scheme. And unlike his boss, DiPascali is willing to name names.
According to a person familiar with the matter, DiPascali has no evidence that other Madoff family members were participants in the fraud. However, he is prepared to testify that he manipulated phony returns on behalf of some key Madoff investors, including Frank Avellino, who used to run a so-called feeder fund, Jeffry Picower, whose foundation had to close as a result of Madoff-related losses, and others. If, for example, one of these special customers had large gains on other investments, he would tell DiPascali, who would fabricate a loss to reduce the tax bill. If true, that would mean these investors knew their returns were fishy. (Lawyers for Avellino and Picower declined to comment. Marc Mukasey, DiPascali’s attorney, says, “We expect and encourage a thorough investigation.”)
The emergence of this potential star witness may well stand assumptions about the case on their heads: Some people widely assumed by the public to have been involved in the fraud may not have been, and a small group of Madoff investors who appeared to be innocent victims may not have been entirely innocent after all. But then, few things about the life of Bernie Madoff turn out to be as they seem.
Before it all went to pieces, Bernard L. Madoff Investment Securities appeared to be a charmed firm run by a tight clan. People believed in Bernie. Nasdaq made him its chairman; the SEC appointed him to industry panels; Congress invited him to testify. New York Senator Charles Schumer stopped by the office in the run-up to the Iraq war and gave a rousing talk on the trading floor. Everywhere you looked, there were signs that Madoff — and by extension his firm — had special status. Bernie was even able to arrange with his friends the Wilpons, owners of the New York Mets, for staffers to play charity softball games on the field at Shea Stadium.
If Bernie was the center of the firm’s solar system, the nearest planet was his brother Peter, the head of compliance and de facto chief operating officer for the Madoffs’ original, legitimate trading business. They were a savvy pair with a long-established dynamic. “They were the ultimate good cop/bad cop duo,” says Christopher Keith, a former chief technology officer of the New York Stock Exchange who worked for the Madoffs on a side project (and who acknowledges that he clashed with them). Peter was the hands-on brother, the one immersed in detail, and most of all, the designated tough guy. “Peter was like five miles of bad road,” Keith says.
Bernie’s role was to glide in at the end and make peace, says Keith, who compares him to the biblical Solomon: “He was the type of person who was sort of above the fray — the wise man.”
Peter, now 63, was tethered to his BlackBerry. A lawyer by training, he was the driving force behind the firm’s technology innovations. Though he couldn’t write code, he could discuss software algorithms with surprising facility.
Bernie didn’t have a BlackBerry. He didn’t even use e-mail — he could barely turn his computer on. His PC was configured essentially just to give him financial news, says Nader Ibrahim, who used to work on the technology help desk at Madoff’s firm. “It was set up in a manner that the computer never shut off,” Ibrahim explains. “So the format on the screens, how his windows were set up, and everything like that would just come up the same way. If he were to touch the stock menu and something [unexpected] came up in front of his system, he would get all flustered and call us.”
Bernie and Peter were the first generation of the dynasty. The second was dominated by another set of brothers, Bernie’s sons, Mark and Andy, now 45 and 43. Andy was the more cerebral one, with a better understanding of complex technological issues. But many viewed him as haughty and unapproachable, though those who know him say a kind person is concealed behind the reserved exterior. Andy survived a bout of lymphoma a few years ago (he is now in remission), and when he returned to the office, he ceased working on the firm’s original trading operation and focused on other projects, such as the Madoffs’ foray into energy trading, a business neither the company nor Bernie was involved in…
