Whitey: The Life of America’s Most Notorious Mob Boss by Gerard O’Neill and Dick Lehr

I bought this book before I knew of its predecessor “Black Mass” written by the same authors and now a motion picture. For some reason I have picked up quite a few books on the New England mob this year. In this book, I feel like I have finally been able to see the Bulger story in its entirety and to better understand how the FBI utterly failed in its role as shepherd for its CI program.

The book outlines the Bulger family history from their initial immigration from Ireland to Newfoundland, Canada and then on to Boston Massachusetts. Like many poor neighborhoods, the bonds between family groups of any single ethnicity can be very tight as people rely on one another to make ends meet.

The Bulger clan is tight and although they all took different roads in life – from State Senator to America’s Most Wanted Man, they all continued to support one another. Whitey spent the majority of his life incarcerated up until John Connelly, his former neighbor became his FBI handler. He did time at Walpole in Boston as well as Alcatraz. Whitey did not waste his time while incarcerated. He was a voracious reader and highly intelligent. A lot of planning went into everything he did and he had a lot of time to examine past errors.

There were so many conflicts of interest in this relationship it’s a wonder that it lasted as long as it did. Connelly was younger than Whitey and looked up to him. He felt indebted to Whitey due to a childhood bullying incident where Whitey had run interference for Connelly.

In addition, once the graft train had pulled out of the station with Connelly firmly aboard and Whitey giving generously, there was no stopping it. In fact, Whitey had such a handle on this that when Connelly started lavishly spending by purchasing a luxury boat which was obviously way outside of his FBI pay check, that Whitey made him return the boat.

In exchange, Connelly provided Whitey with tip offs on everything: when indictments might be handed down, criminal investigations into Whitey as well as his associates, information on opposing gangs and what they were up to in terms of territory and operations. In addition to Connelly, Bulger had state police, local Boston PD and politicians and other city, county and state officials in pocket.
As for Whitey’s 13 years on the run as the second most wanted fugitive, moving up to number one after the death of Osama Bin Laden, I was curious as to how he was able to hide so successfully. The answer in short – easily. Despite the FBI’s press releases that they were all over it or nearly had him, they were not even really looking for the first 12 years.

They had at most one or two agents on the case at any one time. They had hundreds of tips coming in – many very viable that with manpower would have resulted in easy captures. The truth was they decided to focus on Europe and they never wavered from that idea. The truth was, Whitey moved around for about 3 years, had an extensive array of false i.d.’s and then settled with his girlfriend in California.

In the end, the capture was easy. But not due to the FBI. A tipster had to call the FBI three times to finally get someone to take her seriously. His neighbors liked him but were able to make it easy for the FBI to take him down peacefully. He was also a man in his 70’s and from the reading of the book, was starting to get worn down by life on the run.

Whitey Bulger was a bad dude but the FBI look like a bunch of incorrigibly corrupt Keystone Cops. It doesn’t give me any peace to think that this agency is in charge of tracking down the bad guys.
For those without a lot of information about Whitey Bulger and a knowledge base that covers the bare bones of the case, this is a good book, knowledgeably written that provides many details that help explain the heinous nature of Bulger’s criminal enterprises and then the reason he was able to evade capture for so long.

I haven’t seen the movie but I suggest the book first which might help put some of the movie into perspective. Boston, the Irish mafia, a worldwide chase….what’s not to like? And it’s all true.


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