I just reread this book now that I have 14-more years of financial world experience. I enjoyed the first half which primarily deals with the financiers and their transactions, but the second half gets bogged down following the regulators who seem hell-bent on making big arrests of powerful people and advancing their fame and careers more than they care for the actual rule of law.
Most of the financiers introduced are truly repugnant characters, in particular guys like Dennis Levine, Marty Siegel, and Richard Freeman. Levine comes across as a conniving weasel who was basically inept at arbitrage and was able to hide this fact from the ignorant (not everyone) by cheating. Siegel was portrayed as a smug crook who turned crybaby as soon as he had to take his medicine. I can't decide if I disliked Levine or Siegel more. Freeman is the most interesting. He seems clearly guilty of insider trading, and pretty much escaped severe prosecution thanks to his benefactors (Robert Rubin) at Goldman Sachs, along with most of his personal wealth.
While Stewart does some exceptional research, it is also clear that he is engaging in a lot of speculation. The most obvious example is the numerous recounted conversations between all the characters, which is of questionable accuracy and few of which are verifiable beyond what the author was able to extract from a large group of people whose honesty is suspect. This includes all the attorneys, corporate chieftains, and in my opinion it especially includes all the government agents and prosecutors.
There is a lot of myth surrounding Milken, and unfortunately most of it is inaccurate. For one, Milken has always been very guarded of his privacy. Its easy to assume he is this way because he has something to hide, which is a poor argument many people love to put forward these days. For the most part Milken has shunned interviews and has made a best effort to not get involved with the press.
Most of his closest associates remained loyal to him, and he was essentially fingered by the lying criminal Boesky for an accounting irregularity involving $5.3 million in commissions, which is hardly a master-mind criminal gain considering the multitrillion dollar scope of Drexel's operation. By fingering Milken Boesky, who clearly was guilty of insider trading, got off with a mere 3-year sentence and was able to retain some $25+ million at the expense of the people he hurt. To support Boesky's claim, agents entered the home of a young female employee and basically got her to admit guilt through coercion (fear) for something she probably did not actually understand. Unlike Boesky, Milken was never convicted of insider trading, nor was there any clear evidence that he had engaged in it. In fact, Judge Kimba Wood conceded that 4 out of the 5 convictions had zero negative economic impact, however Stewart clearly allows his personal opinions to vilify Milken and paint him out as some genius criminal. So in hindsight, the sum negative economic impact of what Milken was charged for was actually less than $320,000. Considering his operation was trading roughly $1 billion per day, there is clearly an unfair bias present throughout the book.
Milken is arguably the most brilliant financier of our age, and having financed some 3,200 companies, it is unlikely anyone will outperform him anytime soon (if ever). He was largely responsible for economic improvement in the US in the 1980's. He has always been a strong proponent of sound capital structures and responsible use of leverage. Companies that were suffering from inept managers were easy targets for takeover and restructures using Drexel financing. Beyond just junk bonds, Milken employed a vast range of financing methods that provided essential capital, which allowed companies to grow, hire, and prosper. Once it became evident that the Milken tap was shutting down (1987-1991), the market responded negatively as would be expected.
There was much to be gained from Milken's downfall. Drexel's success certainly created a lot of ill will among the old and established Wall Street banks. Since Drexel via Milken was the dominant financier, the destruction of Drexel and the ruin of Milken sent their multibillion dollar financing into the hands of the very competitors who clearly stood to gain. Stewart conveniently ignores this whole side of the equation, which is not fair. It is a good example of the many biases that plague this book. Then we also have the likes of Rudy Giuliani behind the prosecution, and here Stewart tries to argue that Giuliani had such noble intentions and cared so much about the rule of law as opposed to his making a big name for himself and advancing his public career (all this just before he successfully ran for NYC Mayor).
If you are really interested in Milken, the book is worth reading so long as you understand that a lot of the information that is presented as hard and irrefutable fact is actually rather questionable, especially in hindsight. Reading the book for the second time, it felt dated and given that it was released fairly shortly after all the events concluded, is clearly guilty of hype and sensationalism.