Trial Diary: Whitey’s World 101

By Dick Lehr, Globe Correspondent

MIAMI – Fred Wyshak, holder of the law enforcement equivalent of a PhD in Whitey’s World, gave jurors a 90-minute primer on three decades of Boston’s underworld in his opening argument against ex-FBI agent John Connolly.

The question was whether the crash course was too much information for jurors.

Wyshak juggled posters – one a timeline and others featuring photographs of the prime-time players in the epic saga – as he sought to provide background on Whitey and the Boston FBI. He introduced a slew of names, dates, and a host of other gangland murders, crimes and misdemeanors from the Whitey years. Richard Castucci. Brian Halloran. Roger Wheeler. Michael Donahue.

Who are these people? (Answer: all were murdered by Whitey and his gang). The history lesson went on and on and you had to wonder whether the jury was overwhelmed by it all. They could have used a line-up card, a Who’s Who. You also had to wonder what they thought of our beloved Boston after hearing exclusively about its dark underbelly.

The graying Boston fed has been designated a special assistant state’s attorney for the purposes of prosecuting Connolly in the 1982 slaying of John Callahan. Dressed in a dark blue suit, his opening statement illustrated the scope and complexity of the story of Whitey and John Connolly’s FBI.

It was a reminder that the Callahan murder is no simple case. No murder case is, but this one is about so much more than a single, specific act. And Wyshak went far beyond the facts surrounding the 1982 slaying to offer a Cliff Notes version of several decades of Boston history. He talked about Connolly growing up in Southie, and his ties to Billy Bulger. Wyshak talked about so many relationships from Boston’s subcultures of crime, politics, and law enforcement, covering so many years that even he, the expert, at times misspoke a name or date. It’s a huge canvas he sought to portray.

Dick Lehr, a journalism instructor at Boston University and former Globe reporter, is co-author of "Black Mass,'' a definitive book on Whitey Bulger's mob and its infiltration of the FBI.

“I know this is getting a little Byzantine,’’ Wyshak told the eight women and seven men who will decide Connolly’s fate. “Try to stay with me.’’

The government is banking that the heavy dose of historical context will help to persuade jurors that Connolly was responsible for Callahan’s murder. Connolly, Wyshak was arguing, knew Whitey was going to have Callahan killed once the agent warned him about Callahan’s possible cooperation with investigators. Connolly had done it before, he argued – leaked info to Whitey that had resulted in murder, and the former FBI agent did it again with Callahan, he said.

Throughout, Connolly sat at the defense table, listening intently. Dressed in a dark blazer and tan slacks, with his hair looking recently trimmed, Connolly appeared in better shape than he did in recent photos showing him wearing an orange jailhouse jumpsuit. He scribbled notes and was mostly expressionless during the prosecutor’s remarks.

His attorney, Manny Casabielle, was not impressed, calling Wyshak’s history lesson mostly irrelevant to the murder charge at hand. “It’s not fair to take a bunch of mud and throw it at someone and hope some of it sticks,’’ he told jurors. “That is not justice."

Dick Lehr is the co-author of the national bestseller “Black Mass: The True Story of the Unholy Alliance Between the FBI and the Irish Mob.’’ He wrote for the Boston Globe from 1986 to 2003.

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