Fred Wyshak had finally confronted the corrupt FBI agent at the center of the James “Whitey” Bulger scandal at a hearing in Miami in 2008, and he would not let him off easy.
The former agent, John J. Connolly Jr., was denying in open court that he leaked information to Bulger and Stephen “The Rifleman” Flemmi, a tip that allegedly prompted the reputed gangsters to orchestrate the 1982 slaying of Boston businessman John B. Callahan in Florida.
“I had nothing to do with it,” Connolly pleaded.
But Wyshak, a towering assistant US attorney in Boston who was assisting with the state prosecution in Florida, shot back.
“You knew Mr. Bulger and Mr. Flemmi were murderers,” Wyshak said in an epic, heated exchange. “You’ve made some allegations here and I want to see if you know what you’re talking about.”
Come next week, Wyshak will finally have an encounter with the man at the center of the case — Bulger himself.
The trial of Bulger will be the climactic end to what has become a historic prosecution lasting more than two decades by Wyshak and fellow assistant US attorney Brian T. Kelly, now head of the office’s public corruption unit.
Once dubbed Batman and Robin in Boston Magazine, it was they — as younger, aggressive prosecutors — who began to investigate Bulger in the early 1990s and who ultimately succeeded in getting the reputed mobster and his cohorts indicted. And it was their prosecution that ultimately exposed Bulger’s corrupt relationship with Connolly, perhaps the most scandalous episode in the Boston FBI’s history.
It was a battle not only against Bulger, but even against upper echelons of the FBI and the US Department of Justice.
“You had a prosecution team that cared about only one thing, and that was getting to the truth, the facts,” said former US attorney Donald Stern, who held that office at the time the investigation began. “They are dedicated. They didn’t care about politics, or what the FBI thought, or what the State Police thought, they were just determined to unearth the facts — the good, the bad, and the ugly.”
Kelly, now 52, and Wyshak, 60, are also working with Zachary R. Hafer, 37, a fresh face to the Bulger prosecution who has been handling many of the recent court motions, including the successful move to keep Bulger from raising an immunity defense. He has been with the office in Boston for six years and has prosecuted cases ranging from international drug rings to the conviction on money-laundering charges of prominent attorney Robert George.
Legal observers said Kelly and Wyshak’s history with the case will bring not only an institutional knowledge to the prosecution, but also the passion to see it through to a conviction.
“No one knows more about this story than they do, they’ve lived it,” said Anthony Cardinale, a Boston lawyer who represented former Mafia head Francis P. “Cadillac Frank” Salemme during the 1998 federal court hearings that exposed Flemmi and Bulger’s secret relationship with the FBI.
“From a standpoint of career prosecutors, this is the icing on the cake, and it’s the culmination of a lot of work on their part, and I think they’re going to be very happy to end this crazy story,” Cardinale said.
Wyshak was already a seasoned prosecutor who had battled organized crime in New Jersey before coming to Boston. Kelly had prosecuted drug crimes in Southern California.
Wyshak is seen as fierce, quick-tempered in the courtroom. Kelly has what his colleagues call a more smooth, calculated approach.
Together, they began to expose Bulger’s alleged underworld like no one had. Wyshak’s strategy was to levy money-laundering charges in addition to standard gambling counts against area bookies, to get them to flip and talk about organized crime figures. The stakes were raised: The bookies faced years in jail, rather than months. And the strategy worked.
“They were the first to see there was something wrong with the picture here, why wasn’t anyone going after the Winter Hill Gang,” Cardinale said, adding that they defied FBI resistance, and worked closely with local prosecutors and State Police. “It was an interesting combination of forces that finally pushed this thing to a head,” he said.
Bulger and Flemmi were indicted in 1995 as part of an organized crime ring. Five years later, they were named in separate sweeping racketeering indictments that included allegations of murder, following the hearings that exposed their work as FBI informants.
Flemmi has pleaded guilty and cooperated with authorities to escape a death sentence. He is slated to testify against Bulger.
Connolly was ultimately convicted in federal court in Boston of lying to investigators and was sentenced to 40 years in prison in Florida for second-degree murder, in the death of Callahan.
Michael Von Zamft, an assistant Miami-Dade state attorney, said he reached out to Wyshak and Kelly when Bulger’s crew was first implicated in the killing of Callahan, and he later asked Wyshak to assist in the prosecution of Connolly.
He found a yin-and-yang split between the federal prosecutors, with their differing strategies. But he also saw them working closely with local and State Police, confronting Bulger and the FBI.
“They were very offended by this whole thing,” Von Zamft said. “We all felt the same way. These guys were working with the government. Bulger was protected for so long. I know all of that was offensive to Fred and Brian because you have people who believed in the system, and they were seeing people do this to the system.”
Correction: An earlier version of this story had the incorrect middle initial of Zachary R. Hafer.