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Fred Wyshak, one of the good guys, hangs it up

Fred Wyshak, who took down mobsters and corrupt pols and cops alike, never sought the spotlight, but it was always on him as he prosecuted the venal and the vicious.

Fred Wyshak
Fred WyshakWendy Maeda/Globe Staff/File 2013

There’s an old saying among prosecutors, or at least there should be, that once the people you put away for life start getting out of prison, it’s time to retire.

Still, it’s purely coincidence that Fred Wyshak, a legendary federal prosecutor, retired just as John Connolly, Whitey Bulger’s FBI handler, won release from prison because he is terminally ill.

In 2008, Wyshak won a murder conviction against Connolly for tipping Bulger off about a guy who might implicate Bulger in a killing. Five years later, after Bulger was captured following 16 years on the run, Wyshak helped put Bulger away for life, which turned out to be a relatively short sentence, as Bulger was beaten to death by another inmate in 2018.


Wyshak has been putting bad bad guys, such as mobsters, and bad good guys, such as cops and unscrupulous opioid manufacturers, away for more than 40 years, having gotten his start in the DA’s office in Brooklyn. He joined a strike force in Newark and nailed the guy who ran the Jersey family on which “The Sopranos” was based.

He joined the US attorney’s office in Boston in 1989. The feds were riding high, having knocked out the leaders of the Mafia family that ran Boston. But Wyshak gradually realized that the most powerful gangster who filled that criminal void, Whitey Bulger, was a protected FBI informant.

Wyshak spent the next quarter century making friends with honest cops and DEA agents who wanted to nail Bulger. He also made enemies in the go-along-to-get-along culture that was typified by, as he told me, “what was going on at the FBI, and to some extent the ways the US attorney’s office was engaged in willful blindness.”

The Bulger case brought him some of his greatest satisfaction and disappointment. The former had to do with taking those deemed untouchable, like Bulger and Connolly, off the street. But Wyshak was appalled by the tactics his Justice Department colleagues on the civil side used against families of Bulger’s victims after they sued the government for being complicit in those murders. He argued for the victims, to no avail.


“It was legal gamesmanship, not good government and justice,” he said. “It was terrible.”

Mafia boss Frank Salemme’s testimony helped him convict Connolly, but Wyshak didn’t believe in the old Faustian rules of blind loyalty to government witnesses. He took great satisfaction in later winning a conviction against Salemme for the murder of South Boston nightclub owner Steven DiSarro.

Wyshak’s biggest disappointment was an appeals court decision overturning the conviction of Massachusetts Probation head Jack O’Brien.

“I felt it was a righteous prosecution that could have eliminated the patronage system that permeates state government,” he said. “I think that opinion set us back 20 or 30 years.”

Wyshak was fearless and stubborn. Brian Kelly, his longtime colleague and predecessor as chief of the public corruption unit, said Wyshak would dig in his heels, defying superiors without regard for implications on his career.

“His stubbornness was his greatest strength,” Kelly said. “He refused to yield when he thought it was right, and he often was.”

Wyshak didn’t oppose the release of Connolly, who is terminally ill, “but if it’s another Sal DiMasi situation, I wouldn’t like it.”


Wyshak said he opposed the compassionate release of former House speaker Sal DiMasi, whose eight-year prison sentence for corruption was cut short in 2016.

“There was a lot of political pressure to agree to that one,” he said. “I opposed it, but I was overruled.”

Five years later, Sal DiMasi’s still walking around, working as a lobbyist, and Fred Wyshak’s walking out the door.

Still shy of 70, Wyshak is young and sharp enough to do other things in the law. But he’s not trying to impress anyone and is typically blunt about his future.

“I’m so sick of being a lawyer,” he said. “I have no desire to practice law, and I could never be a defense attorney. I want to enjoy life. I’m going to sit on the beach and drink martinis.”

Kevin Cullen is a Globe columnist. He can be reached at kevin.cullen@globe.com.