Whitey Bulger's Wily Girlfriend Catherine Greig

To her friends, Catherine Greig, a five-foot-six, blue-eyed, bleached blond beauty, was a smart woman with a kind heart, a silver tongue, and a boob job worth flaunting.

Back in the day, the dental hygienist lived in a gray one-story house with a white picket fence in Quincy’s upper-middle-class Squantum neighborhood, an eight-minute drive from South Boston, with her two toy poodles, Nikki and Gigi. She was a fixture at the local beauty salons and had her teeth cleaned once a month.

“She was just a decent young woman and highly intelligent,” said Anna Palazzolo, who was friends with Greig’s sister Margaret. “She was hard working, self-sufficient, and educated. She was established on her own.”

Her much older boyfriend, James “Whitey” Bulger, was an established man himself. One of Boston’s most prolific crime bosses from the '70s to the mid '90s—and until his capture last week, perhaps the most famous fugitive in America—he was the feared head of South Boston's murderous Winter Hill Gang, alleged to have killed 19 people, including two women. He did time in Alcatraz, and served as a confidential informant for the FBI in a controversial arrangement that allowed him to maintain his criminal enterprise. Known for his violent temper, Bulger carried knives and guns, brazenly taunted local and federal law enforcement, and had a thing for the ladies.

“They were opposites in a way,” said Kevin J. Weeks of Bulger and Greig. Weeks is the author of Brutal: The Untold Story of My Life in Whitey Bulger’s Irish Mob and the newly released, Where’s Whitey?, a fictional account of Bulger’s life on the run. Weeks was perhaps closer to Whitey than anyone else in Boston. “[Whitey] could have a temper and she was kind of docile," he told The Daily Beast. "She was funny too, she always had a good comeback. In a very nice way she could take you apart with her tongue without you even knowing it. She would sometimes leave [Whitey] speechless.”

The couple had been on the lam since February of 1995, when they vanished after a tip from former FBI agent and convicted murderer John Connolly, just ahead of Bulger’s federal racketeering indictment. It was the beginning of a 16-year manhunt that spanned the globe, and some people wondered whether Catherine Greig would get out of it alive.

The next time authorities set eyes on the elusive couple was last week in Santa Monica where they were passing themselves off as Charles and Carol Gasko. (Charlie was a nickname Bulger was called by a former girlfriend.) The 81-year-old gangster, who inspired the Martin Scorsese crime flick The Departed, and the 60-year-old Greig were living the life of retirees in a modest two-bedroom apartment less than a one-hour drive from FBI headquarters in Westwood.

“I was shocked she was still alive,” said retired Massachusetts state police detective Bob Long of Greig, who investigated Bulger in the 1970s and `80s. “I would have bet money she was disposed of already."

Like her boyfriend, Greig's life has long been shrouded in mystery. She and her twin sister Margaret were born in Boston in April of 1951. While in her early twenties, she married Robert “Bobby” McGonagle, who died of a drug overdose in 1987, and whose two brothers, Donald and Paul, were suspected to have been murdered by Bulger.

Weeks, who was a teenager when he met Bulger and eventually became one of his top lieutenants, believes that Greig met the gangster through mutual friends in the early '70s when she was in her late twenties and he was known as a ladies man. “He was very attractive to women at that time,” said Palazzolo. “He had a lot of power. He was a handsome man. I remember he bought a girl a $650 pair of shoes. I saw the price tag at the bottom of her shoe. She said Whitey had bought them for her. There was a lot of talk he would take girls on trips.”

Bulger eventually sold his townhouse and moved into Greig's gray house in Squantum. But even as the couple was living together, Bulger was leading a double life. He was involved in a long-term relationship with Teresa Stanley, who he had lived with back in the 1970s when she was a 26-year-old single mother with four young children.

“Teresa was absolutely beautiful,” said Weeks, who struck a plea deal with federal prosecutors in 2000 and implicated Bulger in at least five murders before pleading guilty to racketeering and other charges. “No one in Hollywood had anything on her. Guys used to walk into walls staring at her. But Whitey never wanted to get married. He said if you are going to be a criminal, don’t get married. It is not fair to the family and kids. Whatever you do affects them.”

Weeks said Stanley learned about Bulger’s relationship with Greig in 1994—when Greig went to Stanley's home and introduced herself. “Catherine had enough of being the second woman in his life. She showed [Teresa] where she lived with Jimmy. I think she was tired of Jimmy having a dual life with Teresa and her. It was like, ‘hey, choose.’”

At first, Bulger chose Stanley, fleeing Boston with her on December 23, 1994 after Connolly, the retired FBI agent, tipped him off that he was about to be indicted. Bulger was going Christmas shopping with Stanley at Neiman Marcus in Boston when he told her they had to leave town on a “little trip.” They drove across the country in his Mercury Grand Marquis and were returning two weeks later to Boston because no indictments had been filed against him, when Bulger heard the news on the radio that close associate Stephen "The Rifleman" Flemmi was picked up by authorities. He turned the car around and drove to New York instead.

But Teresa had already had enough of the fugitive life. So after a short trip to New York, Bulger dropped her off and picked up Greig. “Teresa missed her kids from a previous marriage,” said Weeks. “Teresa wasn’t mentally prepared for a life on the run.”

Weeks said he drove Greig, who was carrying only a few small bags and had left her toy poodles with her sister, to Malibu Beach in Dorchester, Massachusetts sometime in February to meet up with Whitey. “I made sure I had no tails on me,” he said. When they parted ways, he and Bulger “shook hands and he said he would be in touch.”

“When [Greig] went away with him they clearly had a talk that they weren’t going on vacation,” said Dick Lehr, a former Boston Globe reporter and co-author of Black Mass: The Irish Mob, The FBI, and a Devil’s Deal. “At some levels, she knew what she was getting into. Teresa was probably surprised she was dumped for a younger woman. It was just a ripple in the story that it wasn’t Teresa, but her.”

It took months before agents realized that Greig had disappeared with Bulger. They didn't even know she had left Boston until they dropped by her house and spoke to some of her neighbors.

Robert Stutman, who investigated Bulger in the '70s and '80s as the head of the Drug Enforcement Agency’s Boston office, said he didn’t know much about Greig until she went on the lam. “Everybody I know who knew them said she was in love with him, period,” he said. “People do crazy things for love. It is like going into the witness protection program. You give up everything and that is exactly what she did. There are some women who are attracted by power. That would certainly be the guess of a lot of people I know.”

For a life in hiding, Bulger made a good choice with Greig. “She would be a big asset to him,” said Weeks. “Catherine can move around and she is computer savvy. She is sharp. She can cook and be social without drawing too much attention to herself.”

Two years after they disappeared, Greig was charged with harboring a fugitive. While on the lam, federal authorities said Greig used the aliases Priscilla E. Chandonnet, Helen Marshall, Catherine McGonagle, and Carol Shapeton—and was armed and dangerous.

Over the years, there were thousands of tips and potential sightings of her. She was allegedly spotted in Louisiana, London, Canada, Italy, and Los Angeles. One tipster told authorities that he saw her getting her hair done at a salon in Fountain Valley, 35 miles south of L.A., in 2000.

In 2010, the FBI changed course in its attempt to track down the slippery fugitives. In April of that year, the bureau took out an ad in Plastic Surgery News, a newsletter delivered to 6,000 plastic surgeons worldwide. The ad described Greig as a plastic surgery aficionado who had her breasts done in 1982, and had undergone liposuction, a facelift, and eyelid surgery. The following month, the bureau posted an ad in a newsletter put out by the American Dental Association because of Greig's habit of getting her teeth cleaned so frequently.

Unbeknownst to the FBI, the couple was living a non-descript existence in Santa Monica where they shared a $1,145 two-bedroom apartment in the Princess Eugenia complex on 3^rd Street. They easily blended in among the aging hippies, well-groomed yuppies, and Hollywood actors.

“They seemed like a sweet old couple,” said musician Josh Bond, who lived in the apartment next door. “They were always wearing white.”

Bond spoke to the gangster regularly. “I would always talk to him about music,” he said. “He liked my playing. He gave me a cowboy hat because the music is country blues.”

One day, Bulger showed up at Bond's door with a beard trimmer and gave him advice on how to maintain it by “running hot water over the comb before combing it.” He also gave him stationary, shoelaces, a light for his bike, and a half-empty bottle of Grand Marnier. “He said he didn’t drink. He bought it for someone and he didn’t finish it.”

Greig baked him a loaf of bread.

Santa Monica neighbor Barbara Gluck, a former New York Times photographer, saw a different side. She said Greig was always warm and friendly, but Bulger was not. He had a short fuse and would sometimes berate her when she spoke too much to Gluck. “He would yell, ‘stop talking to her,’” she said. “He had a rageaholic energy. She would stand back and roll her eyes.”

Their life of leisure came to a screeching halt last week when the FBI decided again to launch another campaign targeting Greig, this time focused on daytime TV viewers. The public service announcements ran in 14 cities where they knew the duo had ties (though, ironically, not on local Los Angeles television) and on national networks.

On June 21, federal agents received a tip that the couple was living in Santa Monica. Within hours, agents using a ruse lured Bulger to the garage of his apartment where he was arrested. Greig, who was inside the apartment, was taken away through the back of the building.

Inside the apartment, federal agents discovered over $800,000 in cash, more than 30 firearms including handguns and rifles, several knives, and several pieces of fake identification.

The following day, the couple appeared in a Los Angeles federal court. Bulger, nearly bald and sporting a white beard, cracked a smile when he saw a throng of reporters rush into the room, mocking them by pretending to scribble notes into a notebook. When asked by U.S. Magistrate Judge John E. McDermott whether he had time to read the charges against him, Bulger replied in a strong Boston accent, “I got them all. It will take me awhile to read all of these.”

Greig, whose bleached blond hair is now white, sat quietly by his side. She stared straight ahead, her blue eyes betraying nothing. Her face was washed clean of makeup. When McDermott called her to the podium and asked if she understood the claims against her, she politely answered, “Yes.