THE DEFIANT ONE
EARLY IN 1987, when Roberto Durán was in Miami drinking cerveza and salsa dancing, Winter Hill gangster Joe McDonald was released from federal prison. He headed straight to a liquor store in South Boston where James “Whitey” Bulger and Stephen “The Rifleman” Flemmi made their headquarters.
Joe Mac, as he was known by the few who knew him, was pushing 70 at the time. A Navy veteran subjected to unspeakable horror during World War II, he was the man most responsible for organising crime in the working-class city of Somerville in the 1950s. In the 1960s, he escaped from prison and joined the gangland war that erupted on the streets of Boston; a war that didn’t end until dozens of Irish, Jewish, and Italian hoods were dumped in Boston Harbor, decapitated, disappeared, or otherwise declared very much dead.
A convict up for parole in 2050 told me that he was “a very serious man not to be trifled with under any circumstances.” The Boston office of the FBI reportedly had his photograph on the wall with a caption that read “The most dangerous man in North America.” No one can say just how many murders he committed (his career stretched as long as Durán’s) though one of his enforcers said it was up around 30. He was never indicted, never mind convicted, for any of them. “Guys would just disappear. We knew who made them disappear,” he said. “Keep in mind, they were all scumbags and killers. Joe never killed anybody [who] didn’t need killing.”
In the 1970s, he noted a new breed rising in the Boston underworld. They had no code outside of self-interest, no compunctions against drug dealing or killing women. Two of them were brought into the Winter Hill Gang as partners—Bulger and Flemmi. Joe Mac, an old-school gangster with old-school values, warned against it. He was eventually proven right. Bulger was only months away from being exposed as an FBI informant when Joe walked into the South Boston Liquor Mart.
“I’ve been away for four years and I know what you two have been up to. I get my cut, which is four million,” he said. “I want it delivered to my house and I better not hear a
