A Cat, A Beauty Queen And Whitey Bulger

In the end, it only took a stray cat, an ex-beauty queen, and a racist comment to topple the last New England mob boss. These indeed were the three major factors behind the 2010 capture of James “Whitey” Bulger, the one-time Irish gangster, FBI informant, and aging fugitive.

To clarify: Bulger and his girlfriend were animal lovers who had adopted a stray feline; South Boston-raised Bulger had shot his bigoted anti-black mouth off publicly about President Barack Obama. Both items caught the eye of a one-time Icelandic beauty queen who lived near Bulger, in Santa Monica.

Subsequently, the FBI, stung by criticism about its inaction in pursuing Bulger, launched a TV campaign broadcasting its one time partner’s countenance and true identity. The agency also offered a $2 million reward to any successful tipster. When her Santa Monica neighbor’s face popped up during a TV broadcast, the now-enlightened beauty queen, hungry for the cash, called authorities.

Soon after, an FBI team arrived at Bulger’s comfortable (and rent-controlled) lair to capture him. The news of the Bulger arrest flashed worldwide in hours—and the odd configuration of events created one of the biggest underworld-related media storms of all time.

But despite the endless publicity, the actual apprehension and trial were comparatively insignificant in the annals of New England crime. There was far more to the Boston underworld than just Whitey—and many more fascinating people and events in its history than those connected to Bulger.

Indeed, Whitey had won the title of “Underworld Boss” only by default. He’d achieved that status in the years of the mob’s decline—a collapse which he personally had hastened. (Bulger had played a small (but overrated) role in helping crush his mafia rivals.) But Bulger had ceased to be a public threat or even a gangster years before his final collar.

In reality, he was merely a toothless—if still vicious—criminal anachronism, destined for jail and oblivion. In power and reputation, he never matched the first mafia dons of New England. Admittedly, never again would a New England mob boss go down so publicly—mostly because the infrastructure of organized crime was long gone. The power and glory days of the Mafia and the New England underworld lay back 40 years prior to 2010, at the least.

But the facts behind the final Bulger downfall raise a fascinating question. How did the most powerful set of underworld organizations in New England history sink so low so fast? These gangster enterprises had, for 50 years, annually generated millions of dollars. They fielded ruthless operatives who could maim or kill innocent and guilty alike with impunity. The dons and bosses could make or break political, administrative, and commercial careers, and throw statewide elections with ease.

In the 1960s, the Mafia, alone, was powerful enough to be a worthy opponent of U.S. Attorney General Robert Kennedy and his FBI. Those mid-century Mafiosi wielded great power in labor management, politics, gaming, entertainment, transportation, construction, and dozens of other areas. But by 2000, the Mafia was mostly just a joke punchline. And in 2010, in the person of Bulger, the entire cast of characters was represented by an octogenarian, seedy informant and serial killer (whose victims included innocent men and even some women).

The 110-years old New England underworld saga is an amazing one—and with an odd bookend.