BOSTON — A businessman testifying in the racketeering trial of reputed gangster James "Whitey" Bulger on Tuesday described terrifying moments in 1982 when, he said, Bulger shoved a machine gun between his legs and threatened to kill him if he didn't pay him $400,000.

Michael Solimando, a construction contractor, said a friend of his, John Callahan, had asked him in early 1982 to invest in a building renovation project in Boston.

Several months later, Callahan was killed. Three weeks after Callahan's death, Solimando said he got a call from Bulger's partner, whom he'd known casually years earlier, asking to meet at a bar.

When Solimando arrived, he was ushered upstairs to a room with the shades drawn where Bulger and an enforcer were waiting. Solimando said Bulger immediately pulled out a revolver and stuck it in his face.

"He said, `We want our money,' and I said, `What money?'"

"According to Mr. Bulger, John Callahan had invested their funds in the building, and all they wanted was their money back now that he was dead," Solimando said.

He said he told Bulger that he did not have any business with any of them and that Callahan had not invested anywhere near $400,000 in the building.

"I was sufficiently scared, I'll tell you that. It was very scary at the time," he said.

"I remember saying if I knew John had business with you people, I wouldn't be in business with John," Solimando said.

Bulger, 83, is accused of participating in 19 killings in the 1970s and `80s, including the killing of Callahan. He has pleaded not guilty. Bulger was one of the nation's most wanted fugitives after he fled Boston in 1994 after being tipped by a former FBI agent that he was about to be indicted. He was finally captured in California in 2011.

Solimando is one of several witnesses called by prosecutors who are trying to show that Bulger played a role in the murders to preserve his status as a ruthless gangster.

Solimando said that at the bar encounter, when he told them he couldn't pay, the enforcer handed Bulger a machine gun, which Bulger shoved under a table toward him.

"It was pointed in my stomach and groin," he said.

Solimando said Bulger then warned him not to go to the FBI, state police or Boston police. He said Bulger told him: "We're going to know the minute you open your mouth."

Solimando said Bulger said that if he went into the witness protection program, he would kill his sister and his brother-in-law.

When Assistant U.S. Attorney Zachary Hafer asked Solimando if he could identify the person who put a handgun in his face and a machine gun between his legs, he pointed to Bulger seated at the defense table. Bulger stared intently at him, as he did through much of his testimony.

Solimando said he returned for a second meeting with Bulger and others and showed them documents that proved Callahan didn't have that much money invested in the building. But he said Bulger wouldn't listen and insisted on some "good faith money."

After making two payments of $20,000 each to Bulger, Solimando said he and his brother-in-law sold jewelry, cars, stocks and other items, and got some money Callahan had stashed in Switzerland. Solimando said he paid a Bulger associate the remaining $360,000 and did not report the extortion to law enforcement out of fear. About $180,000 to $190,000 came from his own money, Solimando said.

"It was either that or get killed," he said.

Bulger has denied the prosecution's contention that he was a longtime FBI informant who ratted on members of the rival New England Mafia and other criminals.

Assistant U.S. Attorney Brian Kelly told Judge Denise Casper that prosecutors expect to wrap up their case next week. Bulger's lawyer, J.W. Carney Jr., said the defense case could go through August. But Carney, who submitted a witness list that had been pared down from more than 80 to 37 witnesses, said he may eliminate additional witnesses.

Testimony began June 12.

Loading Slideshow...
  • James "Whitey" Bulger

    Gangster. Informant. Fugitive. These are three words that best described Bulger's life in crime. Born in South Boston, he rose to be a powerful figure in organized crime, and was allegedly involved in drug dealing, extortion, loan-sharking, gambling and other illegal activities. Prosecutors allege that he cemented his place atop the underworld through violence, charging him with 19 murders in the 1970s and 1980s. During those years, however, he was also an FBI informant. HIs relationship with the FBI was corrupt and in 1994 the agent he worked with tipped him off about a looming indictment. Bulger skipped town and became one of the most wanted men in America. Finally, in 2011, he was found living under an assumed identity in Santa Monica, Calif. with longtime girlfriend Catherine Greig. This June 23, 2011 booking photo provided by the U.S. Marshals Service shows James "Whitey" Bulger after his capture in Santa Monica. (AP Photo/ U.S. Marshals Service, File)

  • Bulger, through the years

    These 1984 file photos released by the FBI show James "Whitey" Bulger. (AP Photo/FBI, file)

  • Bulger, through the years

    These 1953 file Boston police booking photos provided by The Boston Globe show James "Whitey" Bulger after an arrest. (AP Photo/Boston Police via The Boston Globe, File, WCVB-TV,

  • Stephen "The Rifleman" Flemmi

    Flemmi was one of Bulger's closest associates in the Winter Hill Gang. He's serving life in prison for 10 murders and is expected to testify as a witness against his former boss, Bulger. In this Sept. 22, 2008 photo, Flemmi is testifying at the trial of corrupt FBI agent John Connolly. (AP Photo/J. Pat Carter, File)

  • Hit man John Martorano

    The prosecution intends to put John Martorano, a hit man who's admitted killing 20 people, in the witness box against Bulger. He served 12 years for the killings. This photo shows him testifying on Sept. 17, 2008 about FBI agent John Connolly, the crooked agent who worked with Bulger when he was an informant for the bureau. (AP Photo/Marice Cohn Band, Pool, File)

  • Whitey Bulger and Kevin Weeks

    Bulger, left and henchman Kevin Weeks strolling on a walk around Castle Island in South Boston in this undated photo. Weeks is one of several former Winter Hill gang members expected to testify against Bulger.

  • Former FBI Agent John Connolly

    Agent Connolly was the FBI handler working with Bulger and his righthand man Stephen Flemmi. Bulger and Flemmi were enlisted as informants, supplying information about the Italian mafia in Boston. But Connolly went rogue and let the Winter Hill Gang off the hook for their own crimes. In 2008, Connolly got a 40-year sentence for helping Bulger's gang murder a businessman in Florida they feared would be a witness against them. Connolly is not expected to testify in Bulger's trial. (Photo by George Rizer/The Boston Globe via Getty Images)

  • Catherine Greig, Bulger's girlfriend

    This undated photo from the U.S. Marshals Service shows Catherine Greig, the longtime girlfriend of Whitey Bulger, who was captured with him, on June 22, 2011, in Santa Monica, Calif. Greig lost her bid to reduce the 8-year prison sentence she received for helping Bulger during his 16 years as a fugitive. A three-judge panel of the 1st U.S. Circuit Court of Appeals said Friday, May 17, 2013, that it found no basis to change the sentence that Greig received after she pleaded guilty to conspiracy to harbor a fugitive, identity fraud and conspiracy to commit identity fraud. . (AP Photo/U.S. Marshals Service, File)

  • H. Paul Rico

    Rico was an FBI agent in Boston who knew a young Bulger and Stephen Flemmi. Later, Rico left the bureau and began working as head of security at World Jai Alai. There, he was reconnected with Flemmi and Bulger, who allegedly skimmed money from the company. He was accused of participating in the murder of Roger Wheeler, a World Jai Alia executive who discovered that gang members were skimming of the top. Rico died in custody in 2004 before gong to trial.

  • William Bulger, the politician brother of the gangster.

    In this May 8, 2003 file photo, William M. Bulger, then-President of the University of Massachusetts, addresses the attendees at the National Public Service Week Recognition Dinner on the campus of Bridgewater State College in Bridgewater, Mass. He's the younger brother of Whitey Bulger and was forced out of his university post because of a controversy about his relationship with his fugitive sibling. For years, he was one of the state's most powerful politicians, serving as the president of the state senate. (AP Photo/Robert E. Klein, File)

  • U.S. Attorney Jeremiah O'Sullivan.

    The late U.S. attorney Jeremiah O'Sullivan is seen in this photo. Attorneys for Bulger contend that the former federal prosecutor gave the Winter Hill Gang boss immunity. Former members federal attorney's office in Boston may be called to testify, including Robert Mueller, who became FBI director and William Weld, who became Massachusetts' governor. (Photo by Barry Chin/The Boston Globe via Getty Images)

  • Edward G. Connors, murder victim

    Connors worked with the Winter Hill Gang, but was not a full-fledged member, according to statements from Stephen Flemmi. He got whacked in a Dorchester phone booth in 1975, according to Flemmi, because he spoke to openly about his role in the killing of James O'Toole. Flemmi said that he and Bulger were ordered to shoot Connors by Howie Winter, who was then the head of the Winter Hill Gang.

  • James "Spike" O'Toole, murder victim

    O'Toole was a South Boston gangster who, according to Winter Hill gang members, tried to kill Stephen Flemmi's brother Vincent Flemmi. Soon after O'Toole completed a prison sentence in 1973 for being an accessory after the fact to a murder, John Martorano ran him over in his car. O'Toole died and Martorano said he was ordered by Bulger to kill him.

  • Edward Brian Halloran, murder victim

    Halloran was a federal informant killed allegedly by Bulger and a masked man in 1982. Halloran's friend Michael Donahue, who had no criminal record, was also killed outside the restaurant where the two had dined.

  • Roger Wheeler

    Roger Wheeler was an Oklahoma businessman who bought World Jai Alai, only to find out that the Winter Hill Gang was siphoning money from the company in a scam. He was killed in 1981 in Tula, because Bulger and his crew feared he'd be a witnesses against them. Rogue FBI agent John Connolly was convicted of helping with the fatal shooting of Wheeler. <em>Correction: An earlier version of this slide incorrectly stated that Wheeler was killed in Florida.</em>

  • Widow and son of an alleged murder victim

    Patricia Donahue, widow of alleged murder victim Michael Donahue, stands with her son, Tommy, outside federal court in Boston, Monday, June 3, 2013, after a pre-trial hearing for accused mobster James "Whitey" Bulger. Jury selection begins Tuesday. (AP Photo/Elise Amendola)

  • Steven Davis, victim's brother

    Steven Davis, the brother of Debra Davis, a woman allegedly killed by James "Whitey" Bulger, stands near the Neponset River where his sister's body was found in Quincy, Mass., on Thursday, June 21, 2012. Davis has been one of the most vocal of the victims' relatives. (AP Photo/Stephan Savoia)

  • Victims' families

    Two sisters of Paul McGonagle leave a plea hearing for Catherine Greig, the longtime girlfriend of reputed Boston mob boss James "Whitey" Bulger, outside the Federal Courthouse in Boston, Wednesday afternoon, March 14, 2012. Paul McGonagle is among the 19 murders Bulger is accused of committing. (AP Photo/Stephan Savoia)

  • The prosecution

    The charges against Whitey Bulger are being prosecuted by the office of the U.S. attorney for the district of Massachusetts. That office is led by U.S. Attorney Carmen Ortiz. The case is being tried by a team of assistants that includes Fred Wyshak and Brian Kelly.

  • The defense team

    Defense attorneys J.W. Carney Jr., left, and Henry Brennan, right, leave federal court in Boston, Monday, June 3, 2013, after a pre-trial hearing for accused mobster James "Whitey" Bulger. Jury selection begins Tuesday. (AP Photo/Elise Amendola)