James “Whitey” Bulger: 25 Things You Should Know About the Captured Boston Irish Mob Legend


After Osama bin Laden’s death, James “Whitey” Bulger was the Most Wanted Man in America. Then after 16 years on the run, the mythological South Boston ex-con was caught yesterday in California. Jack Nicholson’s character in The Departed was loosely based on Whitey, in the sense that Bulger was both the Hub’s most notorious gangster and most surprising FBI informant. But even beyond the drug-running, extortion, murder, money-laundering, snitching, and Scorsese, the nuances of Bulger’s character are legendary. Noses bitten off, soiled pants, puppy tears–examples culled largely from Dick Lehr and Gerard O’Neill’s Black Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob. File under: couldn’t make this shit up.

1. James Bulger is wanted for involvement in 19 counts of murder and a shit-ton of other charges.

2. As a child, James Bulger ran away from home and briefly joined Barnum & Bailey circus.

3. Bulger was first charged with larceny at 13.

4. As a teenager from the South Boston projects, Bulger became best known as a “dangerous delinquent with a Jimmy Cagney flair, known for vicious fights and wild car chases.” He ran with a gang called the Shamrocks and never graduated from high school, but “always had a car when everyone else took the bus.”

5. Boston cops nicknamed the notorious James Bulger “Whitey” because of his lightning-blond hair. He hated the nickname and insisted that his associates (anyone who didn’t want to die) call him Jimmy.

6. Bulger spent nine years in federal prisons for bank robbery from 1956 to 1965, beginning at age 27.

7. Bulger did time in Alcatraz. Officials sent him there after three months in the hole at an Atlanta jail–he was suspected of planning a prison escape.

8. After his maximum-security stint, Bulger briefly worked as a janitor, but ended up as a bodyguard for South Boston crime boss Donald Killeen. A gangland war erupted between Killeen’s crew and their leading Southie rivals the Mullins, and in the process, a guy named Mickey McGuire got his nose bitten off his face.

9. Also during that crossfire, Bulger’s acolyte Kevin Weeks recalls this story in a 2006 memoir:

“One day while the gang war was still going on, Jimmy was driving down Seventh Street in South Boston when he saw Paulie (Paul McGonagle) driving toward him. [Whitey] pulled up beside him, window to window, nose to nose, and called his name. As Paulie looked over, [Whitey] shot him right between the eyes. Only at that moment, just as he pulled the trigger, [Whitey] realized it wasn’t Paulie. It was Donald, the most likable of the McGonagle brothers, the only one who wasn’t involved in anything.

[Whitey] drove straight to William “Billy” O’Sullivan’s house on Savin Hill Avenue and told O’Sullivan, who was at the stove cooking, ‘I shot the wrong one. I shot Donald.’ Billy looked up from the stove and said, ‘Don’t worry about it. He wasn’t healthy anyway. He smoked. He would have gotten lung cancer. How do you want your pork chops?‘”

10. Bulger was a peacemaker during the Boston busing crisis. Why? Police attention in South Boston was bad for his business.

11. Bulger struck a terrifying presence in South Boston. “When a resident accidentally bumped into him coming around a corner in Bulger’s liquor store, the cold hard glare he got was enough to make him soil his pants.”

12. While Whitey Bulger made a career of crime, his younger brother “Billy” was elected Massachusetts Senate President and later appointed President of the University of Massachusetts.

13. A Boston restaurant proprietor owed $175,000 to a friend of Bulger’s, so one night, Bulger and two mobster cronies went to threaten the owner, Francis Green. When Green cried poor mouth, Bulger reportedly told him, “if you don’t pay, I will absolutely kill you. I will cut off your ears and stuff them in your mouth. I will gouge your eyes out.” Meanwhile District Attorney William Delahunt and another prosecutor sat across the dining room.

14. Bulger didn’t drink or smoke, and worked out daily.

15. Julie and Stephen Rakes were a young hardworking couple from South Boston. They decided to put all their money into starting a liquor store and chose an abandoned Texaco gas station in Southie. At the same time, Whitey Bulger decided he needed a new headquarters and liked their location. A week after the Rakes’ store opened, Bulger showed up in the family kitchen with cohort Steve “the Rifleman” Flemmi and told Rakes they were going to buy the business. “It’s not for sale,” Rakes told him.

16. Then the following ensued:

Bulger had a pocket knife in his hand, which he opened and closed as if to punctuate his words. Rakes’s little girl wandered into the kitchen to see what was going on. [Bulger’s rifleman Steve] Flemmi pulled out a handgun from his waist, put it on the table, lifted the girl onto his lap. ‘Isn’t she cute,’ Flemmi said. The gangster tousled her blond hair. The gun’s hard metal caught the girl’s attention, she reached for it. Flemmi let her touch it, and the girl even put part of the gun in her mouth. –Black Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob

17. Bulger bought Rakes’ store for a brown bag full of $67,000. They’d invested more than $100,000.

18. A neighborhood rumor spread that Whitey Bulger had killed Stephen Rakes because no one had seen the former liquor store owner recently. In actuality, Rakes was on vacation in Disneyworld with his family. “One of Bulger’s henchmen tracked down Rakes. . . and ordered him to come back. Rakes left his family, flew home, and, to quiet the talk, stood next to Bulger, Flemmi, and Weeks at a busy intersection so that passerbys could see that he was alive.”

19. Whitey Bulger was traveling with his common-law wife Teresa Stanley when he was tipped off about his impending indictment. That girlfriend, who he’d lived with in South Boston for 30 years, didn’t want to live as a fugitive. So Bulger drove back to Boston a few weeks later, dropped her off, and “promptly” picked up another girlfriend he’d been seeing on the side. That woman was Catherine Greig.

20. In 2002, White’s politician brother Billy Bulger was called to testify before congressional committee investigating the FBI’s use of mob informants and plead the Fifth.

21. One of Bulger’s fugitive aliases was Thomas F. Baxter, an identity he assumed on the side in the ’70s, “even before the real Thomas F. Baxter of Woburn died in January 1979. Bulger obtained a Massachusetts license with his own photograph and Baxter’s name, birth date, and Social Security number. He renewed it every four years.”

22. On the lam in Grand Isle, Louisiana, a grandfatherly Whitey Bulger wept when a dying puppy was shot in the head as a mercy killing.

23. During that same period on the “Cajun Bahamas,” Whitey went fishing once and tossed back all the small fish.

24. Catherine Greig’s hairdresser was the police chief’s daughter in Grand Isle. Whitey’s girlfriend was a generous tipper.

25. Bulger is also believed to have been involved in one of the biggest art heist’s in history, when thieves dressed as policemen stole thirteen paintings from Isabella Stewart Gardner Museum on St Patrick’s Day in 1990. One of the pieces stolen was a Rembrandt.

Quite a guy!

Other sources:Whitey Bulger’s life on the run,” Boston Globe, FBI’s Most Wanted, a Boston childhood.