Flemmi testified that his friendship with Bulger was born out of similarities in their personalities. Both men were healthy and didn't drink or party.
"He didn't drink. He didn't smoke. He worked out regularly. We both had that in common,'' Flemmi told the court.
That friendship soured when Flemmi was arrested and indicted and began serving three life sentences for murders plus 30 years for gun charges. Meanwhile, Bulger became a fugitive living the life of a retiree near the beach in Santa Monica, Calif.
On Thursday, the two former Boston crime lords saw each other for the first time since 1994 and exchanged expletives. Flemmi snared "Motherf***er" to Bulger. The mob boss on trial responded in kind. "F*** you too."
Today Flemmi's testimony was more reserved and centered largely on another aspect of his life that he shared with Bulger. In 1974, both men became FBI informants.
Flemmi was the first to make a deal with the FBI. His handler was FBI agent Paul Rico. That deal paid off rather quickly when Rico, according to Flemmi, tipped him to an indictment that named him in the murder of William Bennett and the attempted bombing of a lawyer named John Fitzgerald.
It was 1969. Rico called him and said: "You and your friend should leave town,'' Flemmi told the court. Flemmi did, moving to Montreal. His "friend" and codefendant Francis "Cadillac Frank" Salemme fled to New York, but was arrested by the FBI.
Salemme was sentenced to 15 years in the case while Flemmi remained a fugitive until 1974 when Rico called again.
"He said, 'The coast is clear,'" Flemmi told the court.
The witness against him, Flemmi explained, had mysteriously gotten cold feet after a visit from hitman Johnny Martorano.
"What happened when you came back?" the prosecutor asked?
"The case was dismissed,'' Flemmi answered. "The witness didn't show up."
Flemmi then told the court he became part of the Winter Hill Gang leadership during a time of mob wars that left Boston's streets stained with blood. The gang's leadership wanted total control over loan sharking, bookmaking and extortion, Flemmi told the court.
They even had a scheme to bribe jockeys to fix horse races at Suffolk Downs.
"Murders?" Wyshak asked.
"Definitely murders,'' Flemmi answered.
Often the mobsters lined a room with plastic before killing someone. "We wanted to stop the blood from going all over the place because we had to clean it up," he said.
By 1974 the men had something else in common. They both became FBI informants as a way to increase connections in law enforcement because it was "good for business."
"It's always good to have connections in law enforcement, law enforcement sources that know what's going on in order to survive,'' Flemmi told the court.
The Italian mob had local police sources. The Winter Hill Gang would have higher-placed sources.
"If they want to play checkers, we are going to play chess,'' Flemmi remembered on the stand.
The Italians wanted Flemmi to become a made man.
"I declined," Flemmi told the court.
But Cadillac Frank Salemme did not, Flemmi testified, saying: "Eventually he became the New England boss."
With the help of the FBI the Winter Hill Gang became powerful. The FBI even had a meeting with the mobsters at the South Boston home of Bulger's mother.
"You weren't meeting him to talk about the Red Sox?" Wyshak asked.
"No,'' Flemmi testified. "Criminal activity."