When real estate developer Richard Buccheri agreed to meet James "Whitey" Bulger in the mid-1980s, he had no idea what the notorious Boston mobster wanted from him. But it became frighteningly clear moments after the two sat down in a screened-in cabana.
"He slammed the table. Then he takes a shotgun that was on the table and sticks it in my mouth," Buccheri said, his voice trembling. "He said he wanted 200... he meant $200 thousand."
Buccheri's testimony on Thursday, during the seventh week of Bulger's murder and racketeering trial, was the latest of many accounts of violence and extortion by people who dealt with the longtime leader of Boston's Winter Hill crime gang. Prosecutors are expected to finish making their case as soon as Friday.
The 83-year-old Bulger, Boston's most feared crime boss during the 1970s and '80s, has been charged in connection with 19 murders. He has pleaded not guilty, though his lawyers have admitted Bulger was a drug dealer, extortionist and loan shark.
Buccheri told the jurors that when Bulger removed the shotgun from his mouth, he picked up a handgun and pressed it against the side of his head.
"He said, 'If you don't pay me in 30 days I'm going to kill you and your family,'" Buccheri said. "I agreed to pay. I got out of the screen house alive."
Bulger faces a life sentence if convicted of the charges stemming from a bygone era when machinegun-toting mobsters left a trail of unsolved killings as they fought for control of lucrative rackets including smuggling and race-fixing, killing anyone they thought might talk to authorities. Prosecutors say Bulger himself was an informant to a corrupt FBI agent who ignored his crimes as long as he informed on other criminals.
His attorneys have conceded that Bulger was an "organized criminal," but dispute the prosecution's contention that he was an informant for the FBI. Bulger insists he took information but never gave it.
The FBI listed Bulger and his main partner Stephen "The Rifleman" Flemmi as informants. On Thursday, Flemmi wrapped up nearly a week of testimony, disputing the suggestion by Bulger's attorneys that he has an easy life serving a life sentence in prison after confessing a decade ago to 10 murders.
"If I gave that food to my dog, he'd bite me," Flemmi said in a rare moment of comic relief.
Flemmi, the prosecution's star witness, has delivered vivid accounts of murders he said he saw Bulger commit. Defense attorneys have been trying to undercut his testimony and that of two other close associates of Bulger.
Among the murders Flemmi described were those of his own girlfriend and his stepdaughter. He said Bulger strangled both women because he believed they knew too much about the gang's dealings and risked tipping off police.
Asked by defense attorney Henry Brennan whether he expected a reduced sentence for his testimony, Flemmi said: "I don't know what the future holds ... Everybody hopes that at some point in the future something beneficial will happen to them. I'm still alive and that's the hope."
The two other associates who have testified against Bulger received shorter sentences in exchange for their cooperation with prosecutors. Flemmi drew a life sentence, but he did avoid the death penalty and kept possession of bank accounts, a laundry business, and numerous condominiums.
Bulger's story inspired the 2006 Academy Award-winning film "The Departed," in which Jack Nicholson played a character loosely based on Bulger.
After fleeing Boston in 2004, Bulger spent 16 years in hiding, evading capture even while on the FBI's "Most Wanted" list. Agents arrested him in June 2011 in a seaside Santa Monica, California home where he lived, keeping a cache of guns and $800,000 cash.