A former hit man who admitted to killing 20 people during his organized crime career took the stand Monday in the trial of mobster James Whitey Bulger. 

John Martorano cut a deal with law enforcement officials in 1999.  He served only 12 years and two months in prison after agreeing to testify against Bulger, his former boss, and Stephen “the Rifleman” Flemmi.  Bulger’s defense team alleges that since being released from prison Martorano has resumed criminal activity but is being shielded by his state police handlers.   

If John Martorano had not become a professional killer he might have been a star football player, having reportedly turned down seven full scholarships after graduating from Milton High School in 1959. Instead, he followed his father, Luigi, into organized crime, working for the Patriarca family and the Winter Hill Gang. 

Born in 1940, by 1960 Martorano had graduated from former alter boy to wise guy; hanging out in Boston’s famed Combat Zone, an adult entertainment district that thrived on prostitution, drugs, human trafficking, and illegal gambling and controlled through violence. 

Boston Herald columnist Howie Carr, a defense witness in the Bulger trial, wrote a book with Martorano called Hitman: The Untold Story of Johnny Martorano.

"I think he just fell under the sway of the Combat Zone," Carr said in an interview. "His father had this place Luigi’s.  He owned it with Sarkis, the famous gambler in Boston and Johnnie just liked hanging around there.  It was the bright lights of the Combat Zone that attracted him."

Aside from his father, one of his teachers in the ways of organized crime was Stephen Flemmi, who in the early 1960’s was a small time hood rising through the ranks of the Winter Hill Gang.   

Martorano’s first hit was on a Patriarca associate who was reportedly planning to testify in a murder case.   The hitman, who would also become known as "The Cook", "The Executioner", and "The Basin Street Butcher" was 24-years-old. In an interview decades after leaving prison on CBS’ 60 Minutes, Martorano said he might be a killer but he was neither a hitman nor a maniac:

MARTORANO: The hitman.  That sounds like to me somebody getting a paid contract.  You couldn’t pay me to kill anybody.  

KROFT: But a lot of people would say you’re a serial killer. 

MARTORANO: I might be a vigilante but not a serial killer. Serial killers you have to stop them. They’ll never stop.  And they enjoy it.  I never enjoyed it. 

Still, Martorano had a fearsome reputation as a hitman. He was the killer that killers called on to get the job done, according to testimony taken during the 2008 trial of former FBI agent John Connolly, Bulger and Flemmi’s long-time protector.

And to kill, Martorano was willing to go considerable distances if necessary, including traveling to Tulsa, Oklahoma in May 1981, where he put a bullet in the head of World Jai Alai owner, Roger Wheeler. Wheeler had discovered a skimming operation taking place under his own roof connected to Whitey Bulger.  

The hitman, who is the prosecution’s star witness in the Bulger trial, was as brazen a killer as he was methodical. Some of Martorano’s victims are rarely recalled.  Some were mobsters caught in a gang war. Others were caught in the wrong place at the absolutely worst time.  Three lost their lives here on Normandy Street on the Roxbury/Dorchester line in 1968.   Their deaths took place against the backdrop of Boston’s deepening racial anxieties.  

On a cold night in January, Flemmi got into a bar fight in the South End with an African American.  Flemmi lost.  He dispatched Martorano, who eventually tracked Herbert Smith to Dorchester. Martorano using a 38-caliber snub nose revolver put a bullet in Smith, but he also killed Smith’s passengers:  17 year old Douglas Barrett and 19 year old Elizabeth Dickson. After news of the murders leaked out, Martorano was a given a new nickname by fellow gangsters.  Sickle Cell Anemia, a sometimes fatal disease that strikes African Americans.  

In 1978 Martorano fled Massachusetts to skirt a race fixing indictment. He resurfaced in Florida while still working for the mob.  The Boston Globe unmaseked Bulger as an FBI informant in 1988.  Eleven years later , Martorano, --after his arrest in Florida - made a deal with Massachusetts, Oklahoma and Florida to turn state’s eviodence against his former boss.  

Since his release, Martorano has expressed remorse for one of his victims: the murder of 19-year-old Elizabeth Dickson in Roxbury.  But, how will the jury in the Whitey Bulger trial view this conundrum: testimony from a man who admitted to murdering 20 people versus a man accused of murdering one just shy of 20?

Martorano’s testimony comes in the early stages of a trial that’s expected to last beyond Labor Day.  By calling him to the witness stand now, the government seems to be making an effort to create distance between an unsavory star witness and the jury’s conclusion to this high stakes legal drama.