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.”