Den of Thieves

The leveraged takeover boom of the 1980s made advance knowledge of deals worth fortunes, and Den of Thieves traces how Dennis Levine, Ivan Boesky, Martin Siegel and Michael Milken exploited it, and how prosecutors brought the scheme down.

Stewart, a lawyer turned journalist, shared the 1988 Pulitzer Prize for Explanatory Journalism, with Daniel Hertzberg, for Wall Street Journal coverage of the 1987 crash and insider trading, and was the Journal's page-one editor while he wrote this book. Kirkus called the reporting damningly detailed and noted that the SEC and Justice Department often appear overmatched and outmaneuvered. Stewart rejects the argument that Milken was unfairly targeted.

That verdict remains the book's main point of dispute. Milken's defenders, including law professor Daniel Fischel in Payback, argued that the prosecution and the press coverage were overzealous, and Milken received a presidential pardon in 2020. Readers should weigh those arguments, but no other book matches this one's detail on how the scheme worked. Pair it with Connie Bruck's The Predators' Ball on Drexel and Bryan Burrough and John Helyar's Barbarians at the Gate on the buyout era. Essential for anyone who will handle material nonpublic information.

1. Deal information is the asset. In a takeover market, knowing who is about to bid is worth more than any analysis, which is why information barriers exist.
2. Small leaks build big rings. The scandal grew from one banker's trades into a network as each participant recruited or traded with the next.
3. Cooperation cascades. Once Levine and then Boesky turned, every relationship they had became evidence, a pattern prosecutors still use.
4. Concentrated power invites abuse. In Stewart's account, Milken's control of the junk bond market gave him leverage over clients and traders alike, Boesky included.
5. Regulators lag the market. The SEC and prosecutors were often outmatched by the firms they were investigating, so firms cannot treat the absence of enforcement as proof of compliance.

The narrative interweaves the careers of the four principals with the investigation that brought them down, moving from the early 1980s to the early 1990s.

1. The rise. Levine, Boesky, Siegel and Milken build careers as takeovers and junk bond financing transform Wall Street, and the value of knowing which company is in play grows.
2. The schemes. Levine trades on confidential merger information through secret accounts; Siegel passes information to Boesky in exchange for cash; and Boesky's dealings with Milken and Drexel include trades and arrangements that later become the heart of the government's case.
3. The unraveling. A tip leads the SEC to Levine, who is arrested in 1986 and cooperates. He gives up Boesky, who agrees to wear a wire and cooperate, setting off a cascade of cases against Siegel and others.
4. The siege of Drexel. Prosecutors pursue Milken and his firm for years while Drexel resists. Drexel pleads guilty in 1988 and collapses in 1990.
5. The reckoning. Milken pleads guilty to securities felonies and is sentenced to ten years in prison, a term later reduced. Stewart closes by weighing what the cases revealed about Wall Street and its regulators.

A #1 bestseller from coast to coast, Den of Thieves tells the full story of the insider-trading scandal that nearly destroyed Wall Street, the men who pulled it off, and the chase that finally brought them to justice. Pulitzer Prize–winner James B. Stewart shows for the first time how four of the eighties’ biggest names on Wall Street—Michael Milken, Ivan Boesky, Martin Siegel, and Dennis Levine —created the greatest insider-trading ring in financial history and almost walked away with billions, until a team of downtrodden detectives triumphed over some of America’s most expensive lawyers to bring this powerful quartet to justice. Based on secret grand jury transcripts, interviews, and actual trading records, and containing explosive new revelations about Michael Milken and Ivan Boesky written especially for this paperback edition, Den of Thieves weaves all the facts into an unforgettable narrative—a portrait of human nature, big business, and crime of unparalleled proportions.