South Boston (Southie) is somewhat of an isolated perimeter on the southern part of Boston harbor. It played a significant role in the Revolutionary War. George Washington mounted cannons on a hill in the center of Southie called Dorchester Heights. The cannons arrived there after a 300-mile trek from Boston to Fort Ticonderoga in New York by a party of men led by Henry Knox, a Boston bookseller. There they acquired the cannons the British left behind after they surrendered Fort Ticonderoga and retreated to Canada in May 1775.
In less than two months, Knox and his men moved 60 tons of artillery and disassembled cannons across lakes and rivers, through ice and snow over the 300 miles back to Boston. The British, upon seeing the canons, realized that they were positioned so that they could easily destroy their fleet. They fled from the harbor.
These tough men freed this country. Many would continue in the service of the Revolutionary Army under Washington. They stand in stark contrast to the detritus in this book who came into being long after these heroes depart.
Many years later Southie was populated predominantly by Irish Catholics with a smattering of other Catholic ethnic groups. The Gustin gang disappeared and eventually the Killeen gang ran the gambling, loan sharking, and related criminal activities in this section of Boston that had about five percent of its population.
Their daily number game attracted and exploited poor folk. I recall my grandfather Jim (Pa) Connolly used to play his daily number always hoping to hit the jackpot someday.
In Olden Days
Like countless others, he and my other grandfather, Patrick (Pa) Rogers, had been born in Ireland and emigrated to the United States settling in Southie. There they met their wives also born in Ireland. Their children went to school in Southie. Many lived there throughout their entire lives. My immediate family moved from South Boston to Savin Hill, less than two miles away from my Southie home when I was ten years old.
Southie was very much isolated from other parts of Boston. It made it easy for one dominant criminal gang to control the area. That gang would have little involvement outside that peninsula. Outsiders, sometimes referred to as strangers, were not welcome. They knew the welcome mat was not out for strangers, so they avoided Southie.
The Killeens dominated the gaming area. There were other illegal side businesses like selling liquor after hours which were independent of them. When we were sixteen or seventeen, we would drive over to the Penn Tavern on West Broadway to buy beer after the liquor stores closed.
We all carried fake identification showing us to be a few years older than we were so that we could buy beer. In those days, licenses were on a thick paper and written in ink. We found we could bleach out the ink and write in whatever we wanted. It did not matter at the Penn because no one checked for identification anyway.
It was convenient but more expensive to do this. We would park across the street from the Penn, sit there and a guy would come out of that bar. He would walk to the car – a six pack of beer cost $2.00 – we’d give him the money, he would go back inside and come out with our order.
One night we were hanging around Savin Hill beach and ran out of beer. We drove to the Penn. The guy walked out the front door over to the car. He said the cops were watching the place. We should drive around the corner to the side street. He would bring the six packs out through the alley. We drove the thirty or forty feet required and got the six pack. I guess the cops were instructed only to watch the front door. They could report no illegal liquor came out of it while ignoring the alley transactions.
Illegal drugs were around. As a young attorney in the late 1960s, I had to deal with the son of a police officer from Southie who had become addicted to them. South Boston had its share of the usual inner-city crimes: breaking into businesses and stealing goods off the back of trucks. With lots of guys working the South Boston waterfront, many products were stolen off the ships. It was not unusual to be approached by someone selling brand new products at highly discounted prices out of the trunk of his car. At the edge of South Boston, the Gillette Factory with its highly desired and easily dispensed razor blades was an especially attractive target.
Southie was not a den of thieves. Those criminals I speak about were a small minority. Most of the folk lived normal hard-working lives with some in professions and many sending their sons and daughters into the professions. It was a place where I walked the streets alone as a young boy and rarely had any problems. Although, on two or three occasions, I was set upon and hurt by bullies. Unfortunately, places get the reputation from the worst living there. That was to be Southie’s fate.
Southie produced James Brendan Connolly, considered the most distinguished of all United States Olympians. On 6 April 1896, he became the first winner at the Modern Olympic Games and the first known Olympic champion in over 1,500 years. In addition to his triple jump crown, Connolly won medals in the high jump and long jump.
WWI produced a large contingent from South Boston in the Yankee Division of the Army, among whom was Michael J. Perkins a Medal of Honor winner. “He, voluntarily and alone, crawled to a German “pill box” machinegun emplacement, from which grenades were being thrown at his platoon. Awaiting his opportunity, when the door was again opened and another grenade thrown, he threw a bomb inside, bursting the door open, and then, drawing his trench knife, rushed into the emplacement. In a hand-to-hand struggle he killed or wounded several of the occupants and captured about 25 prisoners, at the same time silencing 7 machine guns.” My grammar school was named after him.
WWII saw the usual heavy participation of South Boston sons in the war effort. My godfather and uncle, James Patrick Rogers, was killed in a B-17 crash. Three other uncles served, Billy and Bobby Rogers in the Navy and Jim Connolly in the Army.
The war that changed Southie was the Vietnam War. The young wise guys joined up, many went into the Marines, and fought in combat in Vietnam. They came home with thoughts in their minds of improving their lot in life. They had been tailgaters and thieves but having matured in the rice fields, they had a desire for a bigger share of the illegal pot. To get more of the illegal action, they had to move into the territory controlled by the Killeen brothers.
Donald, Kenneth and Edward Killeen had controlled the organized crime in South Boston for many years by the time of the Vietnam War. Those who came back from Vietnam hung around with a group known as the Mullens. The Mullens was a much younger group. They pushed for a cut from the Killeens’ gaming activities; the Killeens pushed back.
The Killeens depended on two tough guys to keep the threats at bay. One was James J. “Whitey” Bulger born in 1929 about whom much would be written. He had gone to federal prison for robbery in 1956. He had been released from prison at age 36 in 1965. He tried to go straight but everything in his body dictated against it. He wanted to be a somebody. All his life he wanted to be something that he really was not.
Whitey was the type of guy who would take credit for a murder when talking to other hoodlums even if he had little to do with it. He murdered few by his own hand. Even so, he had a weak stomach for murder. After a murder took place at which he was present, he would have to lie down and rest, unlike many others he associated with who took pleasure in mutilating bodies. To the time of his death, Whitey reveled in the false idea that he was the number one criminal in Boston. An idea pounded into the public’s mind by some in the media seeking to fry bigger fish. It was almost as if he had to find something to justify his sordid life.
Whitey’s arrival on the scene of the Boston gang wars came extremely late. His involvement in murders pales in comparison to many others. As best we can tell, Whitey did not murder anyone until into his forties, a time when most killers are slowing down. The growth of Whitey’s reputation disproportionate to his actions may be explained by the wrath and anger people had to about political power of his brother, a Massachusetts State Senator. To hurt his brother, Whitey’s criminal life was highly exaggerated.
The other tough guy for the Killeen’s was Billy O’Sullivan. Little is known about his involvement in murders. He was known as a tough guy who carried a weapon and who you never wanted to be on his bad side
The Mullens had their own enforcers: Pat Nee, who called himself an Irishman and a criminal and had served with the Marines in Vietnam; Tommy King, an artist with his fists; Paulie McGonagle; Dennis “Buddy” Roache, whose brother would later become Boston’s police commissioner, and Francis “Buddy” Leonard. All of these enforcers were gifted crooks who hung around a corner in Southie and at a place called the Mullens club. My cousin Roger, though not part of the gang and as tough as any of them, was the bartender at the Mullens club.
The hostilities between the Killeens and the Mullens broke out into the open in 1971 when Kenny Killeen fought Mickey Dwyer, one of the Mullens’ gang. Kenny shot him in the arm and bit off a piece of his nose. The Mullens made a show of strength as they rumbled through the town looking for Kenny. They called out the Killeens. The Killeens would have to respond.
As best I can tell both sides met for a talk. in a bar on Broadway, the main street in South Boston. Two Killeens, Whitey Bulger and Billy O’Sullivan, had occasion to sit down with the Mullens including, Dennis “Buddy” Roache. An argument ensued. Billy O’Sullivan pulled out a gun. He shot Buddy Roache.
Buddy had a different slant on the story. In 1985, he said in 1971 he is in the Colonial Room Lounge in South Boston. He asked two drunks to shut up. He said: “Next think I knew I was down.”
Buddy said he was shot in the shoulder but after complications from a second operation he was paralyzed from the waist down consigning him to life in a wheelchair. It seems Buddy brought the drunks into the story to replace Whitey Bulger and Billy O’Sullivan because he knew his shooting would not go unrevenged. The war was started.