The Biggest Rat: Whitey Bulger’s Decades of Deceit – Part 5 – Whitey’s Out of Prison and Back on the Streets of Boston



Big RatJames Cagney - you dirty rat


Whitey was thirty-five years old when he hits the street of Boston again. By this time, his brother Billy was a three-term state’s representative, and Billy used his massive influence, much greater on the streets of Boston than it has been in the Federal Prison System, to get Whitey a job; ostensibly as a janitor in the local courthouse. But the only time Whitey showed up for work was to collect his $76 a week paycheck.

            After a few weeks of much needed rest and relaxation, Whitey took up with the mighty Killeen gang; as a street collector and enforcer. While in prison, Whitey read us up on the best criminal minds known to man; especially Niccolo Machiavelli, the 16th Century Italian philosopher and realist, who taught precepts like “The end justifies the means,” and “It’s much greater to be feared than to be loved.”

            The Southie-based Killeens were led by three brothers: Donald, Kenneth, and Edward. And they were in constant battle with the notorious Mullin Gang from Winter Hill in Somerville, led by Buddy McLean. Add to the mixture the murderous McLaughlin brothers from nearby Charlestown, and South Boston’s Mullin gang, and by the time Whitey had been released from prison, there was a Celtic War taking place almost every day in and around Boston.

Of course, there was also the New England Italian Cosa Nostra (the feds call it the Mafia, but, in fact, the Mafia exists only in Sicily), who also had a huge presence in Boston. But in the mostly Irish Southie, the Italians took their cuts from whomever was in power, and stood out of the street battles for control of the Irish rackets.

            While riding shotgun for the Killeens, Whitey became fast pals with Italian-American Steve Flemmi; a murderous thug who constantly resisted offers to be inducted into the local Cosa Nostra. The fact that Flemmi repelled proposals to be “made” should have sent sharp signals to the Italian mob that maybe Flemmi was untrustworthy (men were occasionally killed when they refused their “button”). Letting Flemmi slide was a big mistake for the Italian mob, which, at a later date, they would pay for with their freedom.

            In 1934, Flemmi the oldest of three sons was born to Italian immigrants Giovanni and Irene Flemmi. He was raised in an Orchard Park tenement in Roxbury, Mass. Flemmi’s father was a bricklayer, and his mother was full-time stay-at-home mom. Flemmi was described by a former mistress as “mild mannered and personable.” However, two other of Flemmi’s heartthrobs would beg differently, since Flemmi later was involved in their murders; even pulling out their teeth after they were dead so that they couldn’t be identified.

            After being a terror on the streets as a teenager, Flemmi decided to join the United States Army. Flemmi was only 17-years-old at the time and too young to enlist, so he borrowed the identity of a high school buddy who had reached the age for qualification into the armed services. At the time, the Korean War was in full blast, and Flemmi was a wiz with an army- issued rifle. As a member of the 187th Airborne, Flemmi was said to have killed five Chinese the first time he was thrust into battle. Thus, he received the nickname “The Rifleman”; the name of Flemmi’s autobiographical book.

Flemmi’s Army career ended in 1955, and back on the streets of Boston, he got into the loansharking business with Edward “Wimpy” Barrett, who was a key member of the McLaughlin gang. Backed by the McLaughlins, Flemmi moved up the underworld ladder quickly, and by 1958, he had his sticky fingers in many illegal enterprises, including robbing banks. Flemmi’s base of operations was a convenience store in Roxbury, where he planned various schemes and scores.

Soon, Flemmi came across the F.B.I.’s radar, and in 1958, Paul Rico, the same agent who had busted Whitey in 1955, paid a visit to Flemmi’s convenience store. Rico was on a rampage trying to bust up the Italian mob, and he knew Flemmi, even thought he was ostensibly with the McLaughlins, knew enough Italian mob buddies to be able to provide Rico with inside information on their activities.

For weeks, Rico and his partner, Dennis Condon, did a tag team routine on Flemmi, and soon Flemmi realized he had nothing to lose and much to gain in playing ball with the feds. Rico convinced Flemmi to leave the McLaughlins, and change sides to the Winter Hill Mob. When Flemmi met with Winter Hill’s boss, Buddy McLean, he was shocked to discover McLean had also been playing ball with the feds.

The next seven years, Flemmi played both sides of the fence; giving Rico the dirt on the Italian mob, while protecting his cronies in the Winder Hill Mob. In 1965, Flemmi made it official; he became a paid government informant, on the record, with the codename “Jack from Boston.”

The Killeen gang, which ruled Southie, was originally run by four brothers: George, Eddie, Donnie, and Kenny. George was blasted from the scene in 1950, and Eddie was gunned down in 1968. Donnie and Kenny ran their gambling and loansharking business from the Transit Café; a rundown dive on West Broadway. By 1968, Whitey was one of the Killeens top enforcers, and he was mentored by the Killeen’s most feared hitman – Billy O’Sullivan; better known as “Billy-O.”

                By this time the McLaughlin Gang had been decimated by the Winter Hill Mob, and the Mullin gang, named after an old neighborhood war hero, was engaged in daily battles with the Killeens over who was to run Southie’s rackets. The Mullins had a mere 20 men in their gang, and the Killeen’s main strategy was to pick off the Mullins one by one.

Two of the main Mullins were the Irish-born Pat Nee and Boston’s own Paulie McGonagle. One night, Whitey and Billy-O were cruising the streets of Boston, when they spotted, who they thought was Paulie McGonagle, driving on East 7th Street in City Point. They followed McGonagle to his home, and before McGonagle could get out of his car, Whitey pulled alongside and shot McGonagle in the face.

The only problem was it was not Paulie McGonagle Whitey had just killed, but his brother Donnie McGonagle; a hard working guy and a civilian in the Irish gang wars. This was a terrible mistake on Whitey’s part. But it didn’t seem to bother Whitey too much, since, less than an hour later, he and O’Sullivan chowed down several pork chops Billy-O had fried up in Billy-O’s house just a few miles from the scene of the wrong-man hit.

In early 1969, Pat Nee dropped in a Boston bar called the Mad Hatter, which was a hangout for members of all the local Irish gangs, and a place where it was understood nobody was going to get hurt because of gangland differences. Sitting at the bar was Whitey, whom Nee knew only as an ex-bank robber named Jimmy. Nee also knew Whitey was with the Killeens, and he suspected Whitey might have been involved in the Donnie McGonagle shooting; as well as several shootings of others in the quickly dwindling Mullin gang.

Still, the Mad Hatter was a neutral place, where a bloke could have a drink without getting his brains splattered on the bar. So, Nee and Bulger sat at the bar and engaged in small talk; about growing up in Southie and the plight of the Boston Red Sox, who had not won a World Series since 1912.

While Whitey and Nee were shooting the spit, a Mullin gang member named Mickey Dwyer rushed into the bar. Dwyer was an ex-boxer with a beat-up face to start with. But Nee was shocked when he saw that Dwyer was now missing his entire nose, and was bleeding profusely from a hole in the middle of his face all over the Mad Hatter’s floor. Dwyer’s had also been shot in the arm.

Dwyer rushed into Nee’s arms, and told him he had been in the Killeens Transit Café when he had gotten into an argument with Kenny Killeen.

Dwyer told Nee, “That bastard Killeen shot me in the arm, and then he bit my nose off!”

As a couple of Mullin gangster rushed Dwyer to the hospital before he bled to death, Nee told the others Mullins in attendance, “Fuck the Killeens. Let’s go get them!”

At this point, Whitey, the only Killeen in the joint, started having ideas he might be taken out; Mad Hatter, or no Mad Hatter.

But instead, Nee turned to Whitey and said, “Do you have a car?”

After Whitey answered in the affirmative, Nee told him, “Okay, let’s get over to the Transit.”

Several Mullins, including Nee, piled into Whitey’s car, and with Whitey at the wheel, they headed over to the Transit Café – Whitey’s crew’s hangout. But when they got there the Killeens had already vacated the premises.

Nee and Whitey shook hands and bid their goodbyes; both knowing the war was escalating, and they were fighting on opposite sides.

                Sure enough, a few weeks later, Nee was sitting in the passenger seat of a Mullin car as they passed the Mad Hatter. Low and behold, Nee spotted Whitey just about to enter the gang-neutral bar. Since Whitey was technically not in the Mad Hatter, but just outside the front door, Nee split hairs, and he decided “The Mad Hatter Truce” was not in effect.

            Nee ordered the driver to stop the car. Then, he screamed at Whitey, “Hey Whitey, this is for you!”

            Nee pointed a .38 caliber pistol at Whitey, and he commenced firing. Whitey dove to the pavement and hid behind a parked car. Nee fired wildly, as Whitey pulled a pistol from an ankle holster and returned fire. Neither man was able to hit his target, and it’s safe to assume if Nee hadn’t yelled first, Whitey would have been toast, and I wouldn’t be writing this book.

Another time, Nee hid in the bushes in front of Whitey’s mother’s house; waiting for Whitey to make his exit. When Whitey finally did show his face outside the front door, Nee again fired wildly; as Whitey skedaddled back into the arms of his loving mother. Things got so hot for Whitey in the streets of Boston, he sometime hid out at Mom’s for weeks at a time.

Nee got sidetracked for a while by the barroom killing of his brother Peter. Nee tried to avenge his brother’s murder by taking out the known perpetrator; a drunken chap by the name of Kevin Daley. But although Nee ambushed Daly near Daly’s house, shot him five times, kicked him in the face, and spat at him, Daly somehow survived. Daly told the cops who had done him wrong, and Nee was arrested for Daly’s assault.

However, when it was time for Daly to testify against Nee in open court, Daly, hunched in a wheelchair, told the judge his sworn statement that Nee was his shooter was incorrect. Nee took a deep breath and was set loose; back on the dangerous streets of Boston.

While Nee was in prison awaiting trial, Whitey thought his problem with Nee was over. But with Nee back in the game, Whitey figured it was time he did some of the ambushing and shooting himself.

Whitey discovered Nee had abandoned his home in Southie and was hiding out in his girlfriend’s apartment in the Bunker Hill projects in nearby Charlestown. Even though he never left the abode, Nee always had a gun within arm’s reach; just in case.

As was told in the book Whitey Bulger: America’s Most Wanted and the Manhunt That Brought him to Justice, by Kevin Cullen and Shell Murphy, Nee was watching television in his girlfriend’s ground floor apartment with his girlfriend’s young daughter. Nee had a gun hidden under a dish towel on the coffee table.

Nee said, “The light from the TV lit up the window to the apartment, and I could see a rifle barrel pointed at the window. Actually, at me. I saw Whitey’s face. I knew it was him and he had the drop on me.”

As Nee rushed for his gun, the started little girl jumped up.

“She was right in the line of fire,” Nee said. “She was between me and the window. I looked right over at Whitey. He lowered his gun and smiled at me. And then he just disappeared.”

Whitey had just obeyed a gangland rule that you never shoot with little kids in the line of fire.

Nee ran outside the apartment pointing his gun, but Whitey had already jumped into a waiting car. There were several people between Nee and Whitey’s car, so Nee lowered his gun. Whitey’s getaway car burned rubber as it sped away.

“I never regretted not shooting Whitey, because I could have hit anybody, even though I was pretty sure I would have gotten Whitey,” Nee said. “And If I had, a lot of other people would still be alive.”

            By 1972, Whitey figured it was time to make an upwardly mobile move in the rackets. That meant getting rid of the Killeens so he could take over their operations. Whitey figured Donnie Killeen was the toughest and the boss, so he would have to go first. But Whitey discovered something was in the wind, and he may not even have to get his hands dirty.

            On May 13, 1972, Donnie Killeen was hosting a birthday party for his young daughter at his home in Framingham when the phone rang. Donnie answered the call, and it must have seemed important since Donnie kissed his wife and daughter, and told them he’d be back after he took care of some business.

A few seconds later, the partying people inside the house heard loud noises; like exploding firecrackers. Donnie’s wife, Donna, ran outside, and she found her husband slumped dead behind the wheel; with more holes in him than ten pounds of Swiss cheese.

It seemed the murder weapon was an old gangland staple: the Thompson submachine gun, which was also called the “Tommy Gun,” “The Chicago Organ Grinder,” and “The Chopper.” The Thompson submachine gun fires .45 APC cartridges, with a magazine that holds as many as 30 rounds. And by the looks of Donnie Killeen’s body, all 30 rounds may have found their mark.

                With Donnie Killeen six feet under, presumably done in by the Mullin gang, who wanted to take over Killeen’s rackets, his brother Kenny finally decided retiring from the underworld was the smart thing to do. Kenny’s decision was facilitated by a little incident that occurred just days after his brother Donnie had bought the ranch.

            Kenny Killeen emerged onto the patio of his South Boston apartment on Marine Avenue to pick up his morning newspaper. As luck would have it, just as Kenny bent down to pick up the tabloid, a sniper fired a bullet that missed it’s mark, but destroyed the wrought-iron railing of the patio (Remember, Steve Flemmi was called “The Rifleman” because of his expertise in these sort of thing). Kenny darted back inside his apartment before he got the same medicine as the patio’s wrought-iron railing.

            A week later, Kenny Killeen was strolling along City Point when a car pulled up next to him. Whitey leaned out the passenger window; holding a pistol in his hand.

Whitey yelled at Killeen, “Hey, Kenny. It’s over. You’re out of business. No future warnings.”

            That said; Whitey’s car sped away.

Kenny Killeen got the message. He meekly resigned his position as head of the Killeens; effective immediately.

With both Killeens gone, Whitey was now the top-ranking member of the Killeen gang, which was like being a captain in the Swiss navy. So, Whitey figured a meeting with the Mullin Gang might work in his favor. Whitey decided to invite the Howie Winter, head of the Winter Hill Mob, to act as a mediator, so at the meeting’s end, everyone would know who was who and what was what. Whitey figured he’d either emerge from that meeting quite dead, or in a better position than he presently occupied.

            The meeting was set for Chandler’s Restaurant in the South End of Boston. Chandler’s was a well-known Irish mob hangout, where numerous meetings had taken place in the past to determine specific territories for the myriad of Irish gangs.

Representing the Mullins was Pat Nee, Paulie McGonagle (still very much alive), and degenerate-killer, Tommy King. Representing himself was Whitey. Whitey ‘s capable hitman, Billy O’Sullivan, had been taken out by the Mullins in 1973, so as far as the Killen gang was concerned, Whitey was the boss and basically the only member of note.

Howie Winter was considered the top Irish mob boss in Boston, so he sat at the head of the table. To his right was Mafioso Joe Russo, from the North End, who was there to make sure the right decisions were made as far as the Italians were concerned. But it was Howie Winter who ran the show.

Knowing Whitey’s cunning, it’s hard to believe he had not known he had become, throughout the years, one of Howie Winter’s favorite Irish gangsters. Winter knew the Killeens were extinct, so he offered Whitey a position as head of the Southie faction of the Winter Hill Mob. Winter was so enamored with Whitey’s leadership skills; he even offered to bankroll a bookie operation in Southie, where he and Whitey would split the profits.

This basically put the Mullins, who would soon lose that gang name, under Whitey’s leadership. This didn’t sit well with Nee, McGonagle, or King. But since Winter was the big Irish boss backed by the Italians, there was nothing they could do but accept the arrangement.

Whitey gladly took the bargain, but he knew he would have to deal with the disgruntled ex-Mullins in the not-too-distant future.

With Paulie McGonagle and Tommy King technically in Whitey’s crew, Whitey convinced King it was McGonagle, for the betterment of the crew, who had to go. Figuring Whitey was the boss and it’s a bad thing to go against the boss, in 1974, King agreed to take part in the McGonagle hit.

After Whitey enticed McGonagle into his car, Tommy King, sitting in the back seat, put two bullets in the back of McGonagle’s head. They buried McGonagle’s body at Tenan Beach, which had a great view of Downtown Boston. But not anymore for Paulie McGonagle.

A few days later, McGonagle’s car was found near the docks in Charlestown. To throw the law off the scent, Whitey conveniently left McGonagle’s wallet floating nearby his killing; far from where McGonagle’s body was actually buried. It wasn’t until 2000, when Whitey’s underling, Kevin Weeks, began singing to the law about who was buried and where, that McGonagle’s remains were located.

Whitey never liked any loose ends, and Tommy King was a loose end.  

King and Whitey had once gotten into a bar room brawl, and King was cleaning the floor with Whitey when other gangs member pulled King off the bloodied Whitey. This incident was the impetus for Whitey to indorse King’s death warrant; in blood.

In 1975, right after Bulger signed up as a full-fledged government informant, with the only stipulation being that he not kill anybody, Whitey, who had his fingers crossed when he made the deal with the F.B.I., decided to take care of the Tommy King situation. Whitey enlisted killers John Martorano and Steve Flemmi, who by this time was spending a lot of time with Whitey.  

Whitey called King, and he said he needed King for the hit of a Boston hoodlum who needed to go. Whitey picked up King at a neighborhood bar, and he enticed King into the front passenger seat (known as the death seat for good reasons). John Martorano sat in the back seat, and Flemmi followed in a car close behind; driving the back-up car, if needed.

While Whitey and King were making small talk, Martorano shot King several times in the back of the head. Whitey and his boys then buried King’s body in the marshes near the Neponset River, in Quincy. In 2000, it was also Kevin Weeks who led the police to King’s body.

King had been a hot head of sorts who hated cops, and who frequently let the cops know he hated cops. On the same night Whitey killed King, he also killed King’s friend Buddy Leonard. The Leonard killing was a red herring to throw the law off the track.

Before he was whacked, King had told a Boston police detective, who was giving him grief, that if the detective didn’t lay off, he would kill the bull as easily as he had killed numerous civilians. The detective knew that King was not too bright. But he also knew King had the reputation of easily killing people who had pissed him off. So, the detective took King’s threats seriously; as well he should. As a result, the detective went to Whitey, and he pleaded his case. The detective knew Whitey was smart enough to understand killing an officer of the law was bad for business.

Whitey told the detective not to worry, and that he would take care of the King situation. What Whitey didn’t tell the detective was that King was already dead and buried.

A short time later, Whitey contacted this detective, and he told him King would no longer be a problem. By doing it this way, Whitey figured he had at least one Boston detective who owned him a serious favor; in addition to the F.B.I. who was eating pablum out of Whitey’s treacherous hands.



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