Carr is a good story-teller. I enjoy reading his works on the Bulger Gang. Something about his writing makes the story of corruption at the FBI and the decline of organized crime in Boston more accessible than the plethora of other books written about Bulger. Even though Carr admits that much of the material comes from the original Black Mass by Lehr and O'Neill, Carr manages to add enough material for this book to stand out. That is not to say this book is without its problems. Foremost is Carr's bizarre fixation on Billy Bulger. Carr's stinging sarcasm and open hostility towards Bulger means that the book is heavily biased - and that is saying something for a book on Bulger. When viewed from this angle, it appears that Carr reverts more towards sensationalism than documented fact. The result is that his book becomes more like a trashy tabloid than non-fiction.
I have read a lot about Whitey Bulger. I can make up my own mind what a sleazy guy he was. I cannot say the same for his brother. Carr certainly tries to portray him as just as rotten as Whitey; but it is difficult for the reader to accept when considering Carr's acerbic prose. The sarcasm and insults bound nearly every page. In some places I actually felt sympathy for the man! Was he really that much worse than his peers of the era? Were the scandals of Billy Bulger worse than or comparable to the Big Dig scandal? Judging from Carr's book, I have the impression of a career politician who knew how to seize power, hold on to power, and how to use power - for good or bad.
By focusing half of the book on Billy Bulger, Carr makes his book on Whitey stand out. Let's accept the fact that a book on Whitey will sell across the country. A book about a local politician will sell locally. It is an interesting ploy; and Carr does a great job at sensationalizing Billy Bulger's career. Everything that Billy Bulger ever said or did is presented to the reader in the worst possible way. I still do not understand some of the scandals Carr described - and I read the book twice. I know enough that Bulger was not charged with anything. Being related to Whitey does not necessarily make someone evil.
Carr then tries to connect Billy and Whitey beyond a sibling relationship. He tries to insinuate that the two helped one another climb their career leaders. I had a hard time pinpointing this in the book; but it really comes down to the central argument is that Billy Bulger was responsible for John Connolly becoming an FBI agent; and then instructing Connolly to protect his brother. That argument is the basis for the book and the reason for bringing Billy into such prominence in the book. This is based on the testimony of hitman, John Martorano who claims Whitey once told him that his brother had instructed Connolly to keep Whitey out of trouble.
That argument adds an entire new dimension to the Whitey Bulger Saga. I do not believe that Connolly or Morris ever indicated that Billy Bulger was responsible for the corruption of the Boston FBI or Whitey's criminal rampage. However, it is a valid argument. It also does a good job in explaining why the Boston FBI latched onto two petty criminals (Whitey and Steve Flemmi) and catapulted them to the pinnacle of organized crime in Boston.
However, Carr has significant problems in his story. One he bogs the reader down in irrelevancy. For example, he had at least painfully long chapters on Billy Bulger's St. Patrick's Day Breakfasts. The only possible purpose is to show Billy's slow downfall. It is irrelevant. Second, he slips into more seedy tabloid journalism. He repeats every rumor and portrays it as fact. He does not cite his sources well, so readers do always not know where the claims originate. I caught onto this near the end of the book when he was describing Whitey's flight and how corrupt FBI agents and friends of Agent Connolly were panicking on how to protect themselves. What other agents? I have read enough books to discern that only Connolly, Morris, and Rico were actively corrupted. By casually indicated that the entire office was paid by Whitey and actively protecting him seems to border on libel. A second reading found more instances. Carr enjoys repeating the claims that Whitey was a gay prostitute in his early years and that was how he first met Agent Rico. The insidious claim being that an FBI agent was investigating homosexuals or worse, seeking companionship with homosexuals in gay districts. Then he goes on to talk about Whitey and Flemmi raping high school girls at a seedy gym - afterwards paying off their families. Carr actually cites a memoir by a Boston hoodlum, whose avowed purpose was to embarrass Whitey and Flemmi. It got to the point that when I saw Carr citing something I immediately became suspicious....
Overall, I enjoyed the book. I appreciate the sideshow into corrupt politics. I enjoy the fresh take on Whitey. Carr has excellent skills. He shows how two petty, but violent, criminals rose to the top of the underworld and stayed there with the help of the FBI. Carr's description of the collapse of both the Winter Hill Gang and the Mafia was brought about in an effort to place two uninspiring thugs at the top. That story alone makes the book worthwhile. The problem is the distaste and hatred Carr displays towards the subject. Nearly every other book on Whitey shows a more detached unemotional story. Carr writes with obvious emotion and that leads him to rumor and hearsay.