Assessing Whitey Bulger’s place when they write the history of the ‘Boston Irish Mob’

“Irish Mob.” Since the capture of James “Whitey” Bulger on June 22, the phrase has fueled purple print accounts, reports from hyperventilating television reporters and anchors, talk radio, and online sites with all the subtlety of a throbbing tooth. I’ll leave the Whitey-as-urban-myth or Nicholson-in-the-Departed-as-Whitey riffs to others who range from those who have cashed in on the “Brothers Bulger” to those whose dogged, courageous reporting revealed the corrupt deal between Whitey Bulger and the FBI. So absurd has it become that a fine columnist actually offered that Whitey’s brother William should have “tried harder” to steer him away from the wrong path.

One has little doubt that the smile Whitey flashed in court the other day has several retired law-enforcement types sleeping fretfully, if at all. They have every reason to wish that Whitey’s younger brother had somehow achieved that feat.

Back to the phrase “Irish Mob” – specifically “Boston Irish Mob.” How accurate is it and where is James Bulger’s historical niche in it? In his seminal book Paddy Whacked: The Untold Story of the Irish American Gangster, the author, journalist, and organized crime chronicler T.J. English tracks the rise of Irish American crime syndicates from the mid-1800s to the present. English, in a Boston Irish Reporter interview with this writer shortly after the book’s publication, said that Bulger came to head the Boston Irish the “usual way” – through street-smarts, cunning, and ruthlessness. However, what always set Bulger apart, English contended, was a combination of intelligence, coldness of temperament, and an almost uncanny ability to “play people” from fellow gangsters to FBI agents and other law-enforcement officers.

While loosely organized bands of thugs sprouted in Boston’s Irish wards by the turn of the 20th-century, the Gustin gang was first to dominate the scene. Their name came not from any of the members, but from a street off Old Colony Avenue in South Boston. Founded by Steve Wallace and his brothers Frank and Jimmy around 1915, the Gustin gang was at first given the nickname the “Tailboard Thieves,” their specialty being hijacking delivery trucks at intersections. Frank soon proved to be the “brains” of the operation, and with Steve providing the “muscle,” the Gustin crew unleashed a string of armed robberies in addition to their trademark hijackings over the next decade.

In 1920, with the passage of Prohibition, a new enterprise – bootlegging – opened up for the Gustin gang. The Wallaces had already cultivated relationships with numerous politicians, high-ranking and street cops alike, lawyers, and informers through bribes and blackmail, so, despite the Irish gang’s long trail of armed robbery, burglary, gambling, assault, and more, none of its members ever spent much time in a cell; they mostly saw countless charges buried or dismissed.

Competing for customers with numerous other bootleggers, the Wallaces and their gang proved brutal, but they knew there were limits when it came to a certain bootlegger named Joseph P. Kennedy, who was amassing such deep political clout and protection that he was playing on a far different level. The Gustin Gang carved out “rum-running” turf in and around their own Southie shore, landing their own shipments and personally delivering the bootleg liquor to local speakeasies as paid-off cops and Prohibition agents looked the other way.

Before long, Gustin Gang members sporting fake Prohibition agents’ badges were hijacking other bootleggers’ shipments and selling them to their own customers.

Although other Irish gangs operated out of Somerville, Charlestown, Dorchester, and Roxbury during Prohibition, the Gustin crew ruled the roost. However, they soon faced resistance and rage from Italian mobsters entrenched in Boston’s North End who determined to end the Wallace brothers’ contempt for any unspoken turf rules, especially after the Gustin Gang hijacked several trucks that were crammed with bootleg beer belonging to Joe Lombardi’s gang, whose headquarters were at the C.K. Importing company in the North end.

Lombardi and fellow gangster Phillip Bruccola persuaded Frankie Wallace to come to sit-down in their neighborhood. Whether out of cockiness, stupidity, or a blend of both, Wallace agreed. He and his lieutenant, Bernard “Dodo” Walsh, strode into the C.K. Importing Company office and were gunned down.

If the Italians thought they had dealt a fatal blow to the Gustin Gang, Lombardi and his crew were wrong. The Irish, under the ham-fisted leadership of Steve Wallace, held onto some of their criminal clout in Boston and environs, but the Italians had sent a message that they were not going anywhere either. Over the next few decades, the Irish gangs battled each other but declined in influence as the Italians garnered more power.

By 1960, an Irish gang resurgence materialized in the form of Somerville’s Winter Hill Gang and the Charlestown Mob. The Winter Hill operation, headed by James “Buddy” McLean, and the Charlestown Mob, led by Bernie and Edward McLaughlin, had been on uneasy terms at best for some time, but the rivalry exploded into the so-called “Irish Mob War” in the early 1960s. According to many sources, the spark to the deadly conflict was lit when George McLaughlin hit on the girlfriend of Winter Hill “associate” Alex “Bobo” Petricone, who, as the actor Alex Rocco went on to play ill-fated Las Vegas mobster Moe Green in The Godfather. Two Winter Hill Gang members beat up McLaughlin so badly that he ended up in the hospital. Bernie stormed over to Somerville to demand an explanation from Buddy McLean, and the names of the men who attacked George. McLean refused, and McLaughlin vowed to make him pay.

In short order, McLean murdered Bernie McLaughlin in the heart of Charlestown. The war ended with Bernie and Edward McLaughlin and their lieutenants, Stevie and Connie Hughes, dead and with George McLaughlin escaping death only because he was imprisoned. McLean was killed, too, by the Hughes brothers before they met their bloody end, and Howie Winter, McLean’s top aide, not only succeeded him, but he also assimilated the shattered Charlestown Mob into the ranks of the Winter Hill Gang.

The Winter Hill Gang, termed the “Irish Mob,” proved far more formidable than the Wallace brothers and their men of the Prohibition era, vying with the Mafia in Boston and throughout the region. Perhaps their greatest illicit success was the fixing of horse races at tracks throughout the Northeast, but in 1979, a federal investigation brought down Howie Winter and twenty-one others on an array of charges. The stage was set for a rising star on the criminal landscape to take over the gang if he had the nerve, the ambition, and the requisite ruthlessness. His name was James “Whitey” Bulger.

To listen to television and radio reports and read most articles that have gushed since Bulger’s arrest and will do so for weeks to come, one might believe that Whitey singlehandedly created the Boston Irish Mob. As with so much else written or said about him, the divide between myth and reality is stark – if the time is taken to bone up on a little history.