by Gordon Kerr
His money also bought the support of judges, politicians, law enforcement officers and even the city’s mayor, ‘Big’ Bill Thompson, as he joined with the rest of the O’Banion gang in battles against not just the Capone mob, but also the Druggan–Lake Valley gang, the O’Donnell Brothers and the Gennas.
When Capone’s men gunned down Dean O’Banion in his flower shop in November 1924, Police Captain John Stege had Alterie hauled in for questioning. Alterie is reported to have vaingloriously boasted in full view of police officers and the gentlemen of the Chicago press: ‘If those cowardly rats have any guts, they’ll meet me at noon at State and Madison and we’ll shoot it out.’ Not Gunfight at the OK Corral; more like Gunfight at State and Madison, with Alterie as Wyatt Earp and all his brothers rolled into one. Needless to say, the good Captain Stege was far from amused with such inflammatory statements.
Neither did trying to stage a Western-style shootout on the world’s busiest corner endear Alterie to the rest of the gang who did not need the unwanted attention Alterie’s statement brought on them. Bugs Moran met him at the Friar Inn and ordered him to leave town. Alterie hightailed it to Colorado.
Alterie is often given credit for inventing the ‘one-way ride’ where someone is abducted, driven off and never seen again. It may actually have been Dean O’Banion who invented it, but it is probable that Alterie was there at the time. It happened after a North Side gang hanger-on, John Duffy, smothered his new bride after a violent, drunken argument. Waking next morning to find what he had done, Duffy panicked. He needed money and a car to get out of town quick and Dean O’Banion said he could help. They arranged to meet at a bar called the Four Deuces, a South Wabash drinking den run by the Johnny Torrio/Al Capone mob.
Witnesses saw Duffy being picked up by O’Banion in a Studebaker at around 8.00 p.m. with another man in the car. Duffy’s body was later found in a snow-bank ouside Chicago with three bullets from a .38 pistol in his head. A witness claimed to have seen O’Banion and two unidentified men dump the body but later withdrew his statement.
This was all bad news for Capone as the last sighting of Duffy had been at his club. The last thing he needed was unwanted attention being focused on the club which was a haven for illegal gambling, prostitution and bootlegging.
O’Banion protested his innocence, telling reporters: ‘The police don’t have to look for me, I’ll go and look for them. I’ll be at the state’s attorney’s office at 2.30 p.m. Monday afternoon . . . I can tell the state’s attorney anything he wants to know about me. Whatever happened to Duffy is out of my line. I don’t mix with that kind of riffraff.’
There was no need to go and look for them. They failed to get enough evidence to bring charges. They thought that what had happened was that O’Banion and two accomplices had driven the desperate Duffy out to a remote area. When he had got out to relieve himself, O’Banion or one of the others had approached him from behind and shot him in the back of the head, in classic gangland style. Another two bullets were then pumped into him to make sure he was dead before his body was dumped. O’Banion had obviously wanted to avoid the focus an investigation would bring to his organisation and he also sensed a chance to make things difficult for Capone, an opportunity he never missed.
If Alterie was not entirely responsible for the invention of the ‘one-way ride’, he was the progenitor of the ambush murder. This involved renting an apartment close to the home or office of the intended victim and then staging a surprise attack.
One other claim to fame that is unique to Alterie is that he was probably the only gangster to have carried out a hit on a horse. While Samuel ‘Nails’ Morton was riding it in 1923, it threw him. Morton died of his injuries and Alterie blamed the horse. After Morton’s funeral, he rented the horse, rode it to a remote location and shot it. Jimmy Cagney later re-enacted the shooting in the film Public Enemy.
Alterie’s ranch sometimes came in handy. In January 1925, the newspapers in Denver, Colorado, were agog with the news that notorious gangster and member of the Dean O’Banion gang, Louis Alterie, who was wanted by Chicago police in connection with a jewel robbery, was hiding out at a ranch near Castle Rock. When the local County Sheriff went to the ranch to investigate, he was welcomed by a six-foot tall man who introduced himself as Leland Varain. Varain told the sheriff that Alterie had been there but had left. A week later, the Chicago police removed Alterie from its wanted list and Alterie emerged from his alter ego and met reporters from the Denver Post. The sheriff was not pleased to find out he had been duped. In the Post, Alterie was described as ‘Six feet tall, weighs around 200 pounds, extremely dark. From the carefully combed, jet-black pompadour to the spats encasing his shoes, he is a picture of sartorial splendor. . . . Deep chest, wide shoulders, and body mounted on slender legs, and his heavy arms and diamond-covered hands finish the picture.’
In 1935, Alterie was subpoenaed to appear as a government witness in the case against Ralph Capone, Al’s brother, who had been indicted for tax evasion. He observed the usual Mob niceties by at first refusing to say anything in the dock, even to the detriment of a hated Capone. However, a threat of imprisonment for perjury loosened his tongue and he testified against Ralph.
Like every other member of the North Side gang, the end of Prohibition and the Depression hit Alterie hard. In 1932, he lost his beloved ranch as well as just about everything else – the diamonds, the flashy outfits and the expensive car.
When they arrested him on suspicion of the kidnapping of a Chicago bookmaker, Edward Dobkin, he pointed out to the authorities that he would not be as poor as he currently was if he was a kidnapper. He was acquitted when Dobkin refused to identify him.
A few months later, he wounded two travelling salesmen after a drunken brawl with an exboxer called Whitey Hutton, at the Denver Hotel in Glenwood Springs. He was fined and put on probation.
He moved to Santa Fe, but eventually returned to Chicago where he resumed his control of the Janitors’ Union of which he had been president in the good old days. He responded to any resentment with threats of violence and maintained his position, once again improving his fortunes.
Louis ‘Two Guns’ Alterie was involved in some 20 gangster killings during his time as an O’Banion enforcer and was himself gunned down by a blast of machine-gun fire from a nearby first-floor apartment window on 18 July 1935 while walking to his car with his wife. She was walking behind him and escaped unharmed. As he lay on the pavement, fatally wounded, with nine bullets in him, he gasped to his wife: ‘I can’t help it, bambino, but I’m going.’ He died shortly afterwards. His killer, who, ironically, had used the method that Alterie himself had invented, was never caught.
‘Two Guns’ was buried in an unmarked grave under the name of Leland Varain.
James ‘Whitey’ Bulger
It would have been sometime in the late 1950s or maybe early 1960s. Mist drifted in over San Francisco Bay, blurring the rocky island on which the forbidding outline of Alcatraz Federal Penitentiary stood. Not that it mattered in solitary confinement which consisted of windowless steel boxes, into which prisoners were thrown clad only in their underwear. If you slid open the viewing panel on the door of one particular box, you would have seen a strange sight – a man crouching, his weight resting on just his elbows, his knees and his toes, permitting only the smallest areas of his skin to touch the icy-cold steel floor. In this way, he could stop the seering cold from entering his body, sapping his energy. To him, it was a way of preserving some dignity.
The man was James ‘Whitey’ Bulger, although you would have been ill-advised to call him ‘Whitey’ to his face; it was a name he detested. Bulger was serving time for armed robbery following a series of bank robberies in Massachusetts, Rhode Island, and Indiana. He had already been in the federal penitentiary at Lewisburg, Pennsylvania, but when guards learned of an escape plan, he was transferred to Alcatraz, America’s most famous, or infamous, maximum-security facility. It was Bulger’s bad attitude there that got h
im thrown into the hole.
By the mid-1960s, however, Bulger was out, exercising his particular brand of mayhem across South Boston, and by the time the seventies came around he ruled the Boston underworld. His reign lasted until the mid-nineties.
Where is he now? That is a very good question. He could be sitting on a train next to you, quietly reading an evening paper, or he might be the guy you bought a drink for in the bar last night. Since he went on the run in 1995, the only place you would be certain of seeing Whitey Bulger would be on America’s Most Wanted list in which he has featured a record 12 times and in whose top ten he lies second only to Osama Bin Laden himself.
Jimmy Bulger – the name he prefers to be known by – grew up in the Old Harbor housing projects in South Boston, the oldest of six children, another of whom, his brother William ‘Billy’ Bulger, would go on in later life to become President of the Massachusetts State Senate. Known as ‘Whitey’ from an early age because of the natural blond colour of his hair, Jimmy was a wild kid. He is reputed to have had a pet ocelot and, at one point, he ran away to join a circus. Later, while still a teenager, he dated an older woman, a burlesque dancer known as ‘Tiger Lil’. In Southie, the locals’ name for the area, he was always in trouble.
But no matter what, he remained a Southie boy all his life and is fondly remembered by numerous South Boston residents for spontaneous acts of kindness, such as purchasing groceries for widows and providing turkeys for the poor at Thanksgiving.
Paroled in 1965 after nine years and after taking LSD as part of a CIA experiment at Leavenworth Prison in Kansas, Bulger returned to Boston and worked as a janitor for a few years. It was not long, however, before he returned to a life of violent crime, working as an enforcer for South Boston gang boss Donald Killeen. When Killeen was murdered by the Mullen Gang, another Southie grouping, Howie Winter, boss of yet another South Boston mob, the Winter Hill Gang, mediated between Bulger and the Mullens and the remaining Killeens. Winter grew to like Bulger and his no-nonsense methods and made him his man in South Boston. Bulger hooked up with an old friend, Stephen ‘the Rifleman’ Flemmi, a former paratrooper in the Korean War. The two became Winter’s enforcers and Bulger developed a reputation as a man with a fearsome and violent temper. People who owed the gang money tended to pay up when they were told that Whitey might come and pay them a visit.
Throughout his criminal career, Whitey Bulger had one distinct advantage over other Boston criminals; he had the FBI on his team. Both he and Flemmi acted as informants for the Boston FBI office for years, being looked after by a guardian angel, Special Agent John ‘Zip’ Connelly. Connolly had tried to get Whitey to become what was known as a Top Echelon Informant for a long time and Whitey had been reluctant at first, but Connolly persuaded him that he could trust him. After all, they were both Southie boys, were both of Irish descent and had even both attended the same church. Anyway, the Mafia, headed up by underboss Gennaro ‘Jerry’ Angiulo, who had controlled the Mob’s activities in Boston for almost 40 years, already had the police in their pocket. If the Winter Hill Gang went to war with them, there was only one way it could end. So the deal was that if Whitey provided information contributing to Angiulo’s downfall, he would be left alone to carry on his ‘business’. Whitey agreed to do it. ‘If the Mafia can play checkers,’ he said, ‘we’ll play chess.’
In the next few years, Connolly repeatedly bailed Bulger out just when it seemed the force of the law was finally going to be brought down on him. In one instance, when one of Howie Winter’s lieutenants, ‘Fat Tony’ Ciulla, was given six years for race-fixing, he made a deal with the police, testifying against the Winter Hill Gang in return for entry into witness protection. He fingered Whitey and Flemmi, amongst others, but when the indictments were handed out, the names of the two men were strangely missing.
Connolly and his superior John Morris argued that Bulger and Flemmi were helping the FBI to bring down the Mafia. Indicting them for race-fixing would have undone all their work.
Things got even better for Whitey, however, when Howie Winter was convicted and a gap appeared at the top of the Winter Hill Gang. Whitey grabbed the position with both hands. Boston’s most vicious enforcer was now at the top of the tree and he had the FBI on his team.
Whitey’s approach to running South Boston was adapted from the Mafia’s methods. The Winter Hill Gang would not dirty its own hands by selling drugs, loan sharking or by running its own backroom betting shops. Rather, it charged rent to others to do it. It was a subscription fee for being in business. Fail to pay and the consequences were bad – a beating the first time and the wrong end of a gun barrel the next.
He set up headquarters in a garage, Lancaster Foreign Car Service, on Lancaster Street in Boston's North End near the Boston Garden, the arena that, before it was demolished in 1998, was home to two of Boston’s sporting institutions, the Celtics and the Bruins. When police planted bugs in the garage, trying to capture some incriminating evidence from the parade of known bookies who came to pay Whitey his dues every day, they were surprised to come up with nothing. They would have been even more surprised if they’d known that Connolly had, of course, tipped Bulger off.
With the support of the FBI, Bulger felt invincible. Bookmaker Louis Latif had been playing up and one of Bulger’s henchmen, Brian Halloran, escorted him to the Triple O Tavern on West Broadway in South Boston. Bulger wanted to have a chat. It was a brief one. Only minutes after going into the bar, Halloran, waiting outside, saw Bulger and another man carry out Latif’s body, wrapped in plastic, throw it in the boot of Latif’s car and drive off.
In 1981, Bulger organised the killing of Roger Wheeler, chairman of Telex Corp and owner of World Jai-Alai, an organisation that ran the obscure Basque sport of Jai-Alai, beloved of Latinos and Americans. Importantly, it was a game that provided many gambling opportunities. Wheeler objected to the Winter Hill mob skimming money from his organisation in Connecticut and was threatening to go to the authorities. He was shot at his golf club. As a postscript, former World Jai-Alai president John Callahan’s body was discovered in the trunk of his rented Cadillac parked in a garage at Miami International Airport a few months later.
Connolly now came into his own. Investigators working on the Wheeler case asked for photos of Bulger and Flemmi. Connolly refused to oblige saying that if his informants said they had not done it, that was good enough for him. The investigators asked that the two gangsters take polygraph – lie-detector – tests. Again Connolly prevented it from happening. He was eventually forced by his superiors to provide the pictures, but they proved nothing and Bulger and Flemmi got away with it.
By this time, Connolly was wearing expensive suits and John Gotti-style blow-dried hair. Other agents insultingly started calling him ‘John Cannoli’. Meanwhile, his boss John Morris was taking money from Bulger in order to fund an affair he was having with his secretary.
Eventually, the FBI took down Jerry Angiulo, but it was no thanks to information provided by Bulger or Flemmi. They did provide information, but nothing that the FBI did not already know. The really useful stuff was provided by a bookie who informed on Angiulo’s gambling operation and about the building in which it took place. As a result, the Feds planted listening devices in the walls and the result was 23 convictions, including Jerry Angiulo and two of his brothers. Connolly and Morris, of course, skewed the reports to make it seem as if Whitey and Flemmi had played major roles in Angiulo’s downfall, justifying their continued employment as informants.
With the Mafia out of the way, Whitey Bulger now had Boston all to himself. He linked up with disaffected Mafiosi and began to work closely with Angiulo’s successor, ‘Cadillac Frank’ Salemme.
Whitey bought a liquor store – although he hated alcohol and loathed drunks – and the shop next door to it – Rotary Variety. When a Rotary Variety customer won $14.3 million on the state lottery with a ticket purchased from the store, Whitey thought it would be nice if he shared it with him. He and two
of his associates took half the winnings, allowing Whitey to claim $89,000 a year in income and sort out his problems with the Internal Revenue Service (IRS) at the same time.
The FBI helped him out on yet another occasion. He told a South Boston estate agent, Raymond Slinger, that he had been hired to kill him, a threat not to be taken lightly where Whitey was concerned. Cunningly, he told Slinger that he would not go through with it if Slinger paid him $50,000. When Slinger took the story to the FBI and offered to wear a wire to trap Whitey, the agent dealing with the case became very excited, convinced at last, he had a case against Whitey Bulger. Without warning or explanation, however, the case was dropped. The Boston Globe reports that a few days later Bulger told Slinger he was dropping the price to $25,000 and that ‘there wasn't going to be an FBI investigation’. Someone had warned him.
Whitey Bulger is reckoned to have been responsible for at least 18 murders, if not directly then under his orders. However, it was ten-year-old tapes that brought him down. These tapes, recorded covertly in Heller’s Café in Chelsea, a meeting place for bookies, provided police with unimpeachable evidence that Flemmi and Bulger were extortionists.
The bookies were rounded up and, instead of receiving a mere slap on the wrist for their bookmaking activities, they were threatened with far more serious money-laundering charges; it is reckoned that Heller’s owner, Michael London, washed around $50 million a year for the bookies. They chose to make deals rather than face long prison sentences.
Then, in 1990, members of the Winter Hill Gang were arrested after a 15-month Drug Enforcement Administration (DEA) investigation into a South Boston cocaine ring. They did not inform on Bulger but the noose was tightening.
Others began to come forward and, finally, the authorities had enough on Bulger, Flemmi and Salemme to move. All three would be arrested simultaneously to prevent one of them from fleeing. Their plan did not altogether work, though. Flemmi was taken into custody without a hitch, but Salemme fled to Florida and was not arrested until seven months later. Jimmy Bulger, on the other hand, just vanished into thin air.
