THE WINTERHILL GANG
Buddy McLean was the first known boss of the Winter Hill gang. Other than being born in 1930 and being adopted by Portuguese parents, not much is known about his early days. What is known is that by 1960, Buddy and his wife (a Portuguese nurse) had two children and were living on Snow Ter. In the heart of the Winter Hill section of Somerville. The neighborhood back then was mostly an Irish and Italian blue collar area with many bars, lounges, and clubs along Broadway, the main street of Somerville. Members and associates of the Winter Hill gang at that time dabbled in everything from numbers and loan sharking to truck hijacking and shakedowns. They usually gathered at a bar known as the Tap Royal, a social club known as the Winter hill Athletic club, a lounge first known as the 318 Club then as Pal Joey's or a Gin Mill known as the Winter Hill café. All hangouts were located on Broadway. It was around this time the boys got noticed by none other than Raymond Patriaca, boss of the New England LCN (La Cosa Nostra). Buddy McLean and his closest associate Howie Winter would make bi-weekly trips to Federal Hill in Providence R.I. to meet with Patriaca and discuss various deals. Buddy McLean was very respected by the New England LCN members. Raymond Patriaca himself was overheard complimenting Buddy and his new found friends from Somerville by a bug the FBI had planted in his office on Atwells Ave. Buddy's hangout was usually the Tap Royal on Broadway.
James 'Buddy' McLean
Buddy used to have a stool in the back against the wall facing the door that was his. Even if the bar was packed and Buddy wasn't there nobody sat on that stool. I made the mistake one time of sitting on it, as i did, about five guys yelled "THAT'S BUDDY'S STOOL!!!" Well, let me tell you, i was up and out of that stool faster than lightning. Cause Buddy was a real tough, tough guy. He used to fight everywhere. The bars, the streets, the nightclubs, even the docks! He once held a job there as a longshoreman. The thing that threw you about Buddy was his baby face. One guy summed it up perfectly when he said this about Buddy, "He looks like a choirboy, but fights like the devil."


Story told by an old associate of James 'Buddy' McLean
Ballou had a crazy streak, he was known to carry a hundred dollar bill in one hand and a longshoreman's hook in the other. People who crossed him were thrown off guard for a second by the sight of the hundred dollar bill, that second's hesitation gave Tommy just enough time to sink his hook deep into their skull. Another who spent time on the Hill was Rico Sacromone, a tough kid from East Boston. He was a personal favorite of McLean's.
Joe McDonald
In addition to Buddy and Howie there was Joe McDonald. Born in 1917 he was a bit older than the rest of the gang members but was very much respected and feared. Sal Sperlinga and other members of the family were active back then. Sid Tindsley, who would later own 'El Sids', a nightclub on Broadway was a hanger on in those days. An ex-MDC cop turned gangster, Russell Nicholson was also an associate. The 6'7" Nicholson was rumored to be Buddy's bodyguard. After nine years on the force, he resigned the night before he was supposed to go before a board investigating his association with known felons. Tommy Ballou, a tough Irish guy from Charlstown spent almost every waking minute in the Winter Hill cafe.
Although the Winter Hill gang was the dominant Irish gang in Boston, they weren't the only Irish gang. In the South End there was Edward 'Wimpy' Bennett and his two brothers William and Walter. Early members of the Bennett gang was Steve Flemmi, his brother Vinnie 'The Bear' Flemmi and Frank Salemme. In South Boston there were tow major gangs, the Killeen gang led from the Transit café by Donald Colleen, included among their rank was James 'Whitey' Bulger. The other crew in Southie were the Mullins gang. The Mullins had such men as Pat Nee, Paul McGonigle and city council president Jimmy Kelly. In Charlestown there were the McLaughlin brothers, Bernie, George and Edward who was known to one and all as 'Punchy'. With help from the Hughes brothers, Steve and Connie, the Charlestown crew were feared.
George McLaughlin
On labor day 1961, two Irish gangsters from Winter Hill rented a cottage on the Salisbury beach. With them were their girlfriends and their buddy from charlestown George McLaughlin. After drinking all day, McLaughlin was highly intoxicated and grabbed the breast of one of the Winter Hill gangsters girlfriend. Feeling he had been disrespected the Winter Hill gangster got into an argument with George. The argument led to the Winter Hill giving George the beating of his life. After stopping when they thought they had killed him, the Winter Hill guys dumped him on the front lawn of a hospital. Knowing the George's brother Bernie was the leadr of the Charlestown gang, the men hurried to Somerville to tell Buddy McLean their side of the story. When George finally got out of the hospital after a month his brother Bernie went to see Buddy Mclean. McLauglin wanted the two men involved dead, and he wanted McLean to set them up.
When McLean refused, McLaughlin stormed out of his house. Later that night, McLean awoke to his dogs barking. When he looked outside he saw men by his car. After chasing them off by firing his gun he found dynamite strapped under the hood. McLean had had enough. The day after, Halloween, Buddy McLean shot Bernie McLaughlin in front of around one hundred people at 12 noon in City Square Charlestown. Because McLean went to prison for two years on a weapons charge the war didn't continue until 1964. The first official killing is said to have been on March 15, 1964 when George McLaughlin killed 20 year-old William Sheridan in Roxbury. That is untrue though, not only did Sheridan have nothing to do with the dispute, he was also the wrong man. After getting into an argument at a party, George left only to return with a gun. He sought out Sheridan who he wrongfully thought was the man he had argued with and shot him dead. The war was on, in the end 48 men would lose their life. All because one man could not keep his temper in check and his hands to himself.
On May 3, 1964 ex-con Frank Benjamin was having a beer at Walter's Lounge. The bar was owned by Wimpy Bennettt but was run by his brother Walter. The Bennett gang were allies of Buddy McLean and of the Winter Hill gang. Someone forgot to tell Frank Benjamin. After having too many drinks, Benjamin bragged about how he was going to take out the whole Winter Hill gang starting with McLean. When Vinnie Flemmi had heard enough he shot Benjamin. Because he shot Benjamin in front of 20 potential witnesses they had had to burn the bar down. Flemmi wanted to cut the head from the dead Frank Benjamin and leave it on Punchy McLaughlin's doorstep. After realizing the gun he had used to shoot Benjamin had come from a cop, Flemmi decided to get rid of the head and bury it in the woods. On May 4, the body of frank Benjamin was found in the trunk of a stolen car in South Boston minus his head. On May 12, the Charlestown crew struck back. They killed Russell Nicholson, the ex MDC cop turned Buddy McLean bodyguard. On August 20, 1964 the Winter Hill gang killed Wilfred Delaney and Harold Hannon. McLean had a woman set up Willie Delaney. When he showed up with Harold Hannon and saw McLean with a few of his men in the apartment he knew he was in trouble. Before killing them McLean held a blowtorch to their genitals to get information from them. After getting the information he needed he strangled them both and dumped them in Boston Harbor. On September 4, 1964 the body of Ronald Dermondy was found in his car at a red light in Watertown.
The story surrounding Dermondy is a strange one. According to underworld folklore Dermody was in love with a woman simply known to everyone as Dottie from Dorchester. Dottie however was going steady with an other guy. Dermondy went to George McLaughlin with what he thought was a great idea. If McLaughlin would kill  Dottie's boyfriend leaving him free to marry her, Dermody in turn would kill Buddy McLean for him. As a token of good faith he would kill McLean first. On September 2, Dermondy burst into the Capitol café on Broadway in Winter Hill and shot a man he thought was buddy McLean. Unfortunately for Dermondy, it wasn't. He had shot a petty thief by the name of Charlie Robinson. When McLean put two and two together he had his friend Joe Barboza take out Dermondy.
Joe Barboza
Barboza who ran his own gang out of the corner of Bennington and Brooks St. in East Boston was another ally of McLean. Throughout 1964 and 1965 the killings continued. On October 20, 1965 Punchy McLaughlin was killed while waiting for a bus to go to his brother George's trial, he was on trial for the murder of William Sheridan. Joe Barboza and two of his guys caught McLean cold. They shot him nine times, two of the shots were in the genitals and another found  his face. Eleven days later and four years to the day when Bernie McLaughlin had been killed, Buddy McLean was shot and fatally wounded while leaving the Tap Royal and walking by Pal Joey's nightclub and the Capitol theater.
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The killers were the fearsome Hughes brothers, Steve and Connie. Many people thought that with McLean and Punchy McLaughlin both dead and George McLaughlin on death row, that the war was now over. Those people were wrong. On May 25, 1966 Connie Hughes was killed while driving on Route 1 in Revere. On September 24, his brother Steve Hughes was shot by Barboza and his crew while driving in Middleton.
Howie Winter
Although Buddy McLean had been a capable leader the Winter Hill gang did not reach it's peak until Howie Winter took control. Winter realized it was time for the boys from Somerville to play in the big leagues. He began by consolidating all non-LCN criminals and all non-LCN rackets. The late 60's and early 70's brought new faces to Winter Hill. Along with Sal Sperlinga, Joe McDonald and Sid Tildsey there were newcomers John and James Martorano, William Barnoski, Edward 'Brian' Halloran, James Simms, James Flynn and two up and coming gangsters Whitey Bulger and Steve Flemmi. Bulger after being released from prison in 1965 hooked up with the Killeen gang. He started out as an enforcer for them, collecting debts and basically being muscle. The other dominant gang in the area, the Mullins, were constantly at war with the Killeens.
After the killing had gone on for a few years Bulger decided he had had enough. On May 13, 1972 48 year old Donald Killeen was leaving his Framingham home when a gunman shot him in his car. Killeen went out just as his two brothers before him had, gangland style. With Killeen dead Bulger assumed the lead role in the gang. Bulger though, fearing for his life wanted the bloodhshed between the two gangs to end. He hooked up with Howie Winter who mediated peace between the two South Boston gangs. Bulger in return brought all of South Boston rackets under his control, incorporating a lot of Mullin gang members into his group as well. For the time being Bulger controlled South Boston, while Howie Winter controlled Bulger. After taking over South Boston Howie Winter turned his attention to shaking down every bookmaker, loan shark, and drug dealer who didn't come under the control of LCN. From Lowell to Cape Cod, the boys from Somerville made a grab for everyone. In 1968, prominant Lowall bookmaker Jackie mcDermott was told to met Howie Winter at the Holiday Inn on the Charlestown--Somerville line.

The message was simple, you have to pay rent to Winter Hill for the right to stay in business. Not having a problem with this Jackie promptly agreed. Not everyone crossed over that easily. Medford bookmaker Joe 'Indian Joe' Notarangelli did not feel he had to pay rent to anyone. On April 18, 1973 while eaing in the Pewter Pot in Medford, a hitman brandishing a machine-gun mowed Indian Joe down. His brother Alfred 'Indian' Angelli owner of a North station nightspot named 'Mothers' was killed on February 22, 1974.
Between 1966 and 1976, the Winter HIll gang killed 13 men. The weapon of choice in all being machine-gun. Not all were business. After getting the better of Whitey Bulger in a bar-room fight in 1975, Tommy King was never seen again. He is rumored to be buried under the Neponset bridge. In the early 70's Howie moved the base of the organization to a garage at Marshall Street in Winter Hill. The garage was fronted by gang member Gearge Kaufman. Around this time, Howie also began demanding that bars and lounges in Somerville and Cambridge install his pinball and vending machines. A crime he would later be convicted of.
By 1975 the Winter Hill gang was the second largest criminal organization in Massachusetts. Being second meant they had to pay the first group, the Patriarca LCN (La Cosa Nostra) family a tribute. Every week Howie would meet with Jerry Angiulo at the Nautica Café and give him $20,000.  Jerry Angiulo, the underboss of the Boston's LCN and overall boss of Boston gladly accepted it. The boys from Somerville were now very much in the big league now. It was time to set their sights higher, on bigger crimes. Starting in 1974 and continuing to 1976, the Winter Hill gang with help from master race fixer Anthony 'Fat Tony' Ciulla began fixing horse races. From Massachusetts to New Jersey, the group bribed jockeys and made millions. Fat Tony was arrested and eventually rolled on the Winter Hill gang ratting them out. With Fat Tony as star witness the government was eventually able to put away many Winter Hill gangsters. Howie Winter, William Barnoski, Sid Tildsey, James Simms, Joe McDonald and James and John Martorano were all charged with the crime.
Two people not charged were Whitey Bulger and Steve Flemmi. The reason why they weren't charged would come out 16 years later, they were both FBI informants. Winter, Barnoski and James Martorano would serve time for their crime. Sid Tildsley would be shot and killed on Somerville Ave. and Simms, McDonald and John Martorano would all go on the lam. The year was 1976, the bulk of the Winter Hill gang was either in prison, on the run or dead. Left behind were two men who would take the lead, Whitey Bulger and Steve Flemmi.
Part One