BOSTON — A woman who survived a gangland hit that left her boyfriend paralyzed and his friend dead choked back tears Thursday at James "Whitey" Bulger's trial as she recalled ducking down in the front seat of a new Mercedes Benz when she heard a hail of gunfire.
Diane Sussman de Tennen, who was shot in the arm, was the first of a series of witnesses who described being wounded or losing a loved one in shootings allegedly orchestrated by Bulger and his gang. Family members of several victims gave emotional testimony describing how they learned their relatives had been killed.
Bulger, now 83, is charged with playing a role in 19 killings during the `70s and `80s while allegedly the boss of the mostly Irish-American Winter Hill Gang. He has pleaded not guilty. His lawyers say he made millions through drugs, illegal gambling and loan-sharking, but they have said his former associates have fabricated or exaggerated his role to get reduced sentences for their own crimes.
Bulger became one of the nation's most wanted fugitives after he fled Boston in 1994. Prosecutors say Bulger had secretly worked as a high-level FBI informant and provided information on members of the rival Italian-American Mafia, once the top federal crime-fighting priority.
Sussman de Tennen said she was in a car driven by Michael Milano – a 30-year-old bartender – on March 8, 1973, when a car pulled up to them at a stop light in Boston's North End neighborhood.
"All of a sudden, there was this noise, a continuous stream of gunfire. ... It was just nonstop," she said.
After the noise ended, she got up and saw Milano, who was leaning forward into the steering wheel.
"I looked at him and I asked him if he was OK, and I got no response," she said.
When she looked in the backseat, she saw that her boyfriend, Louis Lapiana, was seriously wounded. She later learned that he had been paralyzed and spent the next 28 years as a quadriplegic before he died in 2001.
Prosecutors say Milano was killed because he was mistaken for another man who was the intended target.
Milano's brother Donald also testified, crying as he recalled how he was on his way to work when he heard on the radio that his brother had been killed. He had seen him the day before when his brother gave him a ride in his new Mercedes.
"He was very proud of it," Milano said.
Under cross-examination by Bulger's attorney, J.W. Carney Jr., Sussman de Tennen said she did not see who shot at the car.
When Carney asked if she knows who shot Milano, she declined to answer, saying it would be speculation.
"In my mind, I do know," she said.
Former hit man John Martorano testified this week that he shot Milano in a case of mistaken identity. Al "Indian Al" Notarangeli, the leader of a rival group, was the intended target.
Sussman de Tennen said she stayed with Lapiana for two years. She cried as described breaking off their relationship.
She eventually married and had children, but kept in touch with Lapiana for the rest of his life. Her children knew him, and his parents were like a second set of grandparents to them, she said.
"To this day, I am emotionally connected to Louis," she said.
Relatives of several other victims also testified.
Deborah Scully, who grew up in the same South Boston housing project as Bulger, said she was 9 months pregnant in March 1973 when her boyfriend, William O'Brien, was shot and killed. Scully said she was unable to go to O'Brien's funeral because she had just given birth to their son.
Ralph DeMasi, a man who was in the car with O'Brien but survived the shooting, also testified. DeMasi, who was released in March after serving 21 1/2 years in federal prison in an unrelated case, did not want to take the stand but was ordered to do so by Judge Denise Casper.
DeMasi said he had a meeting the day of O'Brien's shooting with Tommy King, a Bulger rival who prosecutors say was later killed by Bulger's gang.
After the meeting, DeMasi said he got a sinking feeling when he saw King get into a car with three other men. He said he told O'Brien – who had given him a ride to the meeting – to speed up if a car came up alongside them.
DeMasi said O'Brien laughed.
"All of a sudden, a car pulls up, people start shooting at us. When it was over, Billy O'Brien was dead. I had eight bullets in me," DeMasi said.
DeMasi said he did not see who shot them.
During cross-examination, Bulger's lawyer asked DeMasi if during his time in prison, he learned that inmates who become government witnesses know they can get "extraordinary benefits," an obvious reference to plea deals struck by Martorano and two other Bulger associates who are also expected to testify against him.
"Absolutely," DeMasi said.
When he asked if the benefits of cooperating were generally known to inmates, DeMasi gave an answer that appeared to reference Martorano specifically. Martorano, who admitted killing 20 people, served just 12 years in prison after cutting a deal with prosecutors.
"Guys are walking the street after they killed 20 people, if they cooperated," he said. "That's the way the government works. You kill 20 people, go testify against somebody, you can walk."
CORRECTION: A previous version of this article named de Tennen's boyfriend as "Louis Lapiano." His name is Louis Lapiana.
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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, thebostonchannel.com)
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 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)
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 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)