He would help old ladies cross the streets of South Boston and give turkey dinners to his working-class neighbors at Thanksgiving.
But authorities say he also would put a bullet in the brain of anyone who double-crossed him and that his mood would brighten after spilling someone else's blood.
For years, James "Whitey" Bulger was viewed as a Robin Hood-like figure on the streets of South Boston, valued by his neighbors who saw him as a tough guy who kept drug dealers out of their neighborhood.
That image was shattered when authorities began digging up bodies.
Bulger was charged in 19 murders, but fled in 1995 after a former FBI agent tipped him that he was about to be indicted. The public would only later learn that Bulger had been an FBI informant for years, all while allegedly committing a long list of crimes.
Bulger, now 81, was finally captured Wednesday in California, 16 years after he disappeared from Massachusetts, embarrassing the FBI and triggering an international manhunt.
"You could go back in the annals of criminal history and you'd be hard-pressed to find anyone as diabolical as Bulger," said Tom Duffy, a retired state police major who was one of the lead investigators in the criminal case against Bulger.
"Killing people was his first option. They don't get any colder than him," said Duffy.
Bulger, nicknamed "Whitey" for his bright platinum hair, grew up in a gritty South Boston housing project. He became one of the most notorious criminals in Boston while his younger brother, William Bulger, became one of the most powerful politicians in Massachusetts, leading the state Senate for 17 years.
Along with Stephen "The Rifleman" Flemmi, Bulger led the violent Winter Hill Gang, a largely Irish mob that ran gambling, loan-sharking and drug rackets in the Boston area.
He became an FBI informant in the 1970s, providing information on his gang's main rival, the New England Mob. At the time, bringing down the Mafia was one of the FBI's top priorities.
In the working-class neighborhood of Southie, Bulger's neighbors knew he had been in and out of prison for various crimes, but he used a mix of charm and intimidation to create an image of a tough but generally harmless gangster.
"If there was an elderly woman carrying a bag of groceries across the street, he would take the groceries and carry them for her," said Duffy. "People liked that about him. It gave them the psychological feeling that their neighborhood was being protected when he was around."
Paul Sassone, 44, said Bulger once gave him money to replace his muddy sneakers.
"At first, I didn't know who he was," Sassone said. "Then he started naming people that I knew and stuck out $60 and said, `Get you some new shoes.' I swear to God, that's what he said."
To law enforcement, Bulger was one of the most ruthless killers they had ever known.
"I think he enjoyed killing," said Massachusetts state police Det. Lt. Stephen Johnson. "We know from people who were there that post-murders, he would act super-relaxed. His associates said he would be in a good mood for a long time after he killed someone."
John McIntyre, a 32-year-old fisherman from Quincy, was allegedly killed by Bulger in 1984.
Investigators say former Boston FBI Agent John Connolly Jr. tipped Bulger that McIntyre had talked to U.S. Customs agents in an investigation of Bulger's involvement in a failed plan to send guns to the Irish Republican Army aboard a Gloucester fishing boat.
Flemmi testified during a civil lawsuit filed by McIntyre's family that Bulger lured McIntyre to a party, chained him to a chair, interrogated him at gunpoint for five hours, then tried to strangle him with a rope. When that didn't kill him, Bulger asked, "Do you want one in the head?"
"Yes, please," McIntyre responded.
The first bullet failed to kill him, so Bulger shot him a few more times, according to Flemmi.
Bulger is also accused of strangling Flemmi's girlfriend, Debra Davis, carrying the 26-year-old down the stairs as he choked her. Flemmi testified that Bulger said she had to die because Flemmi had told her that he and Bulger were FBI informants.
Bulger associate Kevin Weeks testified that Bulger also strangled 26-year-old Deborah Hussey, the daughter of Flemmi's common-law wife, because she had a drug problem and used their names whenever she got in trouble.
In both cases, Bulger insisted on pulling out the women's teeth so they would be difficult to identify, said Flemmi.
"The scope of his criminal activity was like a tornado. It cut a wide swath and it damaged and destroyed people's lives," said William Christie, an attorney who represents the McIntyre family.
Authorities said Bulger went on the run after being warned by Connolly, who was convicted in 2002 for protecting Bulger and Flemmi.
Bulger became one of the nation's most-wanted fugitives, with a place next to Osama bin Laden on the FBI's "Ten Most Wanted" list and a $2 million reward on his head.
One of the more bizarre episodes involving Bulger in Boston came in 1991, when he won a one-sixth share of a $14.3 million state lottery jackpot, worth $1.9 million paid in 20 annual installments. The ticket was purchased at a South Boston liquor store in which Weeks _ who also won a one-sixth share _ held the lottery license, according to city records.
Federal prosecutors seized Bulger's lottery winnings in 1995 after he fled, though claims were later made on it by a sister of Bulger's and relatives of his alleged victims.
An inspiration for the 2006 Martin Scorsese film, "The Departed," Bulger is only about 5-feet, 8-inches tall and 150 pounds. But he only had to give a look or raise his voice to instill fear in people.
"He had a menacing voice, and everybody knew he knew how to pull a trigger without remorse," Johnson said.
"He enjoyed the dog-and-pony show he would put on when he was extorting someone," Johnson said. "There wasn't anyone who said no."