Whitey Bulger’s Handler – When Silence Does Not Help

When after more than two hundred years Ireland slowly came out of its “to hell or Connaught”  days, it discovered that some of the male descendants of those who had lived through this era in the hostile, boulder strewn, barren lands of the west had gathered themselves into opposite extremes.  A man in one of these groups would be seen luxuriating in a brooding silence often in front of a three-quarters filled pint of Guinness nary uttering one word from sun up to sun set as if intent on solving the most vexing problems of creation; a man from the other group at the far end took all the words left unsaid by the former, added  the many that seemed to overflow inside him, multiplied it by a hundred, as if possessed of an uncontrollable impulse to engage in endless chatter even if the only audience was the man in front of the neglected Guinness pint or just the pint itself.

On Fridays I try to write about John Connolly.  Today I will talk about one of his most obvious characteristics.

John Connolly descended from the voluble side of the spectrum.  He was no stranger to hyperbole.  He loved an audience.   His friend FBI ASAC Dennis O’Callaghan who testified for him at his trial said it was impossible to have a short conversation with him.   Dick Lehr in Black Mass tells of meeting him on a cold February morning walking down the street.  Connolly immediately launched into a tale about how the FBI successfully bugged the Italian eatery, Vanessa’s, in the Prudential Center, a matter that had never been publicly disclosed.  Connolly knew Lehr was a reporter for the Boston Globe.  John Ford who became a friend of Connolly’s testified that when he was a clerk in the Boston FBI office he heard the office staff talking about Whitey Bulger being an informant for Connolly.  He became concerned with the loose lips so he went to Connolly to express this.  Connolly was not the least bothered and then told him that aside from Whitey, Stevie Flemmi was also his informant.

Connolly was not only talkative but he was indiscreet.  He felt a compulsive need brag about things.  There’s little problem with that in social settings but when you’re involved in a serious life or death business then it can cause trouble.  Some people like Connolly have been described as having verbal diarrhea or logorrhea, often engaging in incessant chatter so that their words run ahead of their thoughts, they say things just to keep the silence at bay sometimes letting loose thoughts they intended to keep to themselves.

John Morris, Connolly’s supervisor, testified that whenever they had a dinner or social gathering, Connolly, Whitey and Stevie would arrive together.  Connolly was continually meeting with them, especially Whitey.   It all provided for a very explosive atmosphere when a person some would describe as a braggart with secretive knowledge engages in a conversation with people whose livelihood depends upon knowing the secrets of the other side.

The law makes no distinction between the voluble and the silent.   As a defense lawyer my advice to every client was to stay silent when confronted by a police officer.  I’ve never known anyone who helped himself by talking.  As a prosecutor I knew that silence was deadly to me because the bread and butter of prosecution are admissions.  A person uttering what she thinks is something inconsequential may find herself undone by a prosecutor who patiently patches together her insignificant utterances with other factors that turn them into admissions.

I’ve criticized Connolly for his in-court silence both at the motion hearings and at his trial in the face of damnable evidence.  I can guess how it came about.  His lawyers advised he remain silent, the traditional advice of a defense lawyer.   It was reported that when approached by investigators for the FBI Connolly refused to be interview.  He provided some information through his lawyer.  US Attorney Donald Stearn  testified that when approached by his office Connolly through his lawyer refused to cooperated.  He took the Fifth Amendment on two separate dates  when called upon to testify.

How is that to be explained?   How is it to be justified?  How does silence help when you have a story to tell?   That is what those who now seek to defend Connolly must explain.  They must tell us why he did not defend himself when he should have done this.

When FBI director Louis Freeh visited Boston in early August 1999 to explain an investigation that was ongoing into the activities of the Boston FBI office with respect to its handling of informants, Connolly faxed a statement to local newspapers stating:  “At no time during my entire career did I engage in any conduct in violation of those policies or existing laws” and he maintained  that all his actions with Whitey were “done with the full knowledge, approval and direction of my superiors in the Department of Justice.”

Yet when the fat was on the fire he sat silently and let himself be consumed.  He sat down when he should have stood tall.  How then is he a victim?

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