On the day of Flemmi's arrest, news spread quickly, and before long, bulletins were broadcast on local television and radio. But Bulger was already far from Boston. He "just happened" to be on vacation with Theresa Stanley, the woman he had lived with for 30 years. Authorities later found out that he had spent the week between Christmas and New Year's in New Orleans.

Stanley apparently didn't like the idea of living on the lam, so Whitey brought her back to Boston in mid-January and picked up his longtime girlfriend Catherine Greig, whom he'd been seeing for ten years while living with Stanley. Greig seemed more willing to play Bonnie to Whitey's Clyde. On January 17, 1995, Whitey surfaced on Long Island, where he bought himself a new car, paying $13,000 by bank check. He and Greig then drove to Grand Isle, Louisiana, where they befriended a poor local couple and their children.

Calling themselves "Tom and Helen from New York," according to the Boston Globe, they first introduced themselves to the couple when they stopped to admire the family's dogs. Bulger and Greig are known to be dog lovers. Bulger's generosity won over the family, and over time he bought them various kitchen appliances and eyeglasses for the children, always paying with $100 bills. The grateful couple invited "Tom and Helen" into their home, often cooking for them. Like a stern but concerned grandfather, Bulger frequently advised the children not to watch violent television shows. It wasn't long before they looked like one big happy family, with Tom and Helen taking the grandparent roles. This was exactly how Whitey wanted it. Investigators believe that he's used this strategy several times to blend into a community and hide in plain sight.

Since 1995, Bulger sightings have been reported in Louisiana, Wyoming, Mississippi, California, and New York. Bulger is on the FBI's Ten Most Wanted List, and on the FBI's Web site, his photo appears underneath Osama bin Laden's. Investigators from the Massachusetts State Police, the FBI, the Boston Police, the Massachusetts Department of Correction, and the state Parole Board are actively pursuing him. Four members of this task force work full-time on finding Whitey.

Bulger is now 75 years old; Greig is 54. Authorities believe that the natural color of his hair has gone from white-blond to white or silver. In the time since the original 1995 racketeering charges were leveled, authorities have filed murder charges against Bulger in the slayings of 18 individuals. According to his FBI's Most Wanted poster, "he has a violent temper and is known to carry a knife at all times."

John Connolly, Bulger's guardian angel at the FBI, retired in 1990, but he maintained contacts with the Bureau and continued to aid Bulger. A federal probe into FBI shenanigans inside the Top Echelon Informant Program began to uncover Connolly's unholy relationship with Whitey Bulger. In 1999, Connolly was arrested and charged with racketeering, racketeering conspiracy, conspiracy to obstruct justice, and obstruction of justice. The government stated that Connolly had warned Bulger of the 1995 indictment against him, giving him ample opportunity to be "on vacation" when officers came looking for him. Connolly vehemently professed his innocence but ultimately received the maximum sentence allowed by law, 8 years and one month to 10 years and one month.

Connolly's supervisor John Morris, who had accepted $7,000 in bribes from Bulger, retired from the FBI in 1995. In October of that year he received a phone call at the FBI Academy in Quantico, Virginia, from Bulger, who ranted and cursed, accusing Morris of double-crossing him. Bulger was also upset because he felt that the FBI was unfairly smearing his brother, Massachusetts State Senate President William Bulger, spreading the rumor that the brothers had been in contact after Whitey had become a fugitive. In 1998, Morris was granted immunity from prosecution in exchange for his testimony in which he laid out the full extent of his and Connolly's cozy relationship with Whitey Bulger and Stephen Flemmi.

After nearly two decades with the Massachusetts State Senate, William Bulger was named President of the University of Massachusetts. During his tenure, he was constantly hounded by rumors and accusations that he was in contact with his brother. As a result of the allegations, he resigned from office in the summer of 2003.