Whitey Bulger’s Case Epitomizes The Phenomenon of The Monday Morning Quarterbacking By People Not Involved In The Game

I received a comment yesterday from a person who said the last murder Whitey is charged with happened 28 years ago. He said if Whitey committed over 50 murders is it likely he just stopped back then. He asked whether he was suspect in any other murders during the last 28 years.  His question in a nut shell is:  does as serial killer suddenly stop murdering people? Probably not. Is he suspected in other murders? Not that I know of.

A good comment like that got me thinking how much we’ve all become Monday morning quarterbacks when we think of Whitey and his murders. The Monday morning quarterback has the advantage of looking to see what happened after the event and then suggesting she would have done it differently back at the time. You know: “Belichik should not have gone for it on fourth down at the fifty, I knew he’d not make it. I would have kicked.”  The problem with that type thinking is that after the fact we see the results of a decision clearly. Then we mentally move back to a position in time before the fact and assume we knew then what was going to happen afterwards..

This has never been more obvious than in the matters involving Whitey Bulger. I was involved in investigations targeting Whitey’s organization in the Seventies and Eighties without knowing they were connected parts of his empire. I worked closely with law enforcement officers who were targeting him directly. I knew he was reputed to be a leader of organized crime in Southie and had a connection to Winter Hill. I had good reason to believe he was involved in extortion, hijackings, bookmaking, leg breaking, fencing, possibly drugs, and other criminal activities. I assumed he may have had something to do with killing people but no specific people in mind.

Now that the feds have loosened the tongue of some of his cohorts, we hear he was involved in upwards of fifty murders, even though he has been indicted for nineteen. It is commonly assumed among people reading about these matters that his involvement in these murders was well-known back then. It wasn’t.  I knew of no one who knew of his involvement in these murders.

Kevin Weeks who was Whitey’s daily companion and enforcer wrote on page 86 of his book, Brutal, about Whitey saying: “One of the first things Jimmy taught me was to consider the long-range ramifications of whatever we did. The idea of committing a crime was to get away with it.”

Whitey did not publicize himself or his actions. I know this from the cops who chased him. He was extremely disciplined. He liked to operate at night and on rainy days. He’d turn up the music in his condo when he talked to anyone; would not talk in cars; and did not hang around drinking. He was so elusive that pictures of him were as rare as hen’s teeth. As Weeks’ noted, he only told you what you needed to know. Weeks said he never asked him any questions about anything and he was as close to Whitey as anyone.

Whitey may have been able to perform some of his criminal activities because of the help of the FBI, but that was not the only factor. He lived a very controlled life style, as one with a reputation of being a brutal man who was both feared and admired in Southie. Few people wanted to brush up against him. If asked why, none could suggest any specific incident that made them fearful but a general sense that he’d best not be messed with.What we think we know now about Whitey’s murders we did not know before 1998.

It was then the Rat Parade began that we began to hear the stories about the murders. The rats knew about the murders because they were there doing the killings. They say Whitey was with them. The three big rats, Martorano, Weeks and Flemmi, prior to jumping into the feds boat, all operated according to Whitey’s principle that the idea behind “committing a crime was to get away with it.”  That meant they did not go around telling people what they had done. They murdered and kept it to themselves. They left no witnesses, no one who could tell other people. Each murder was encapsulated so that less than a handful of trusted people knew about it, and all were participants who could not talk without implicating himself.

The feds admitted this in giving Martorano a sweetheart kiss of a sentence.  They said they would not have had any knowledge of the murders if he did not confess to them. If they didn’t know, how did anyone else?

Once it appeared the fellow murderers were jammed in by the feds, they figured another way to get away with their crimes and that was by becoming rats. They justify their ratting by saying Whitey was an FBI rat. But that doesn’t hold water for these guys because Whitey never ratted on them. In fact, if you listen to the way some people talk, Whitey didn’t rat on anyone, he took information from the FBI for his own use and gave back, as Flemmi once said, “garbage, we got gold and gave them garbage.”   The real reason they became rats is that none of them could do time, something Whitey always worried about.    

I felt compelled to write this because as I discuss the murders Whitey is charged with committing it is important to keep in mind that they occurred between 1973 and 1985. Other than the people who did them, no one else had any evidence he was involved in these killing until almost 15 years later. Yet we’ve all become Monday morning quarterbacks judging both Billy Bulger and John Connolly harshly, one has been incarcerated, the other excoriated, for not doing something about what they, like the feds, like the rest of us, did not know. Tomorrow I’ll write about Whitey’s involvement in the murders.