The Worst Woman in Sydney

by Leigh Straw

  The battlegrounds were clearly drawn between the leading crime figures. Phil Jeffs, Kate Leigh and Tilly Devine each controlled large groups of underworld crooks that were firm in their allegiance to each of the leaders. Phil Jeffs started out as a small-time gangster in Sydney before making a fortune in nightclubs. He was the owner of the notorious 50-50 Club in Kings Cross, which became a base for his sly-grog and cocaine dealings. It also placed him in direct competition with Kate Leigh. Jeffs’ success lay, however, in his ability to market an image of himself as a respectable after-hours businessman. He was one of the first to make a fortune from the club culture of the Cross. When Jeffs died in 1945, possibly from complications from a bullet wound during the razor wars, he had amassed a fortune from the sale of his clubs. Yet his hold on those clubs, and avoidance of consorting charges, was enabled by powerful connections. Jeffs was defended by state parliamentarians and seems to have come to an agreement with local police. He would be arrested only for minor charges if he provided inside information to the police.

  Matilda ‘Tilly’ Devine (née Twiss) was an English-woman who met and married Australian soldier James Devine in London during the First World War. Jim holds an unenviable record as one of the most disreputable soldiers in the Australian forces. A former shearer from Victoria, he was repeatedly detained for being absent without leave and was declared an ‘illegal absentee’ by May 1918. It probably had more to do with the fact he had married Tilly in August the previous year and was absconding to see her. Tilly’s occupation is not given on the marriage certificate, but she was a well-known prostitute.

  When Tilly arrived in Sydney in 1920, aboard a warbride ship, she was reunited with Jim and the pair set about making as much money as possible from her work. As a hire-car proprietor, Jim was able to get Tilly away from police quickly when she was sighted soliciting for sex. By the middle of the 1920s, Tilly owned a number of brothels and both she and Jim were peddling cocaine. The pair moved out of inner Sydney to a house in Maroubra, which became the centre of their operations. It was a violent, volatile marriage that ended in divorce in 1943.

  Violence went beyond the Devine marriage and erupted on the streets of eastern Sydney from the middle of the 1920s. In November 1926, Norman Bruhn, an underworld figure from Melbourne intent on making it big in the harbour city, got involved with cocaine and prostitution and started ripping off the leading crime figures, including Kate Leigh and Tilly Devine. He was a ruthless gangster who often slashed rival thieves and cocaine traffickers with a razor in alleyways. Bruhn didn’t last long and was shot in Darlinghurst in June 1927, only eight months after arriving from Melbourne. He lingered in St Vincent’s Hospital before succumbing to his wounds, having never given up the name or names of those who had fired at him.

  Police and the state government reacted quickly to the rise in gang and gun violence. The Pistol Licensing Act passed in 1927 brought with it severe penalties for carrying concealed weapons. It forced the crooks to get crafty. Their weapon of choice now was the razor, preferably the Bengall cutthroat sort available from most chemists and grocers. Razor slashings increased by the hundreds and, again, the press made the police look like a laughing stock. The razor took urban warfare to new heights of violence.

  The Commissioner of Police, Walter Childs, was furious. He told the papers the situation was under control and he would enlist more men to deal with any rising violence. He was under immense pressure to do something or step aside and make way for someone else. A detective inspector in the Sydney Criminal Intelligence Branch, William Mackay, was eyeing the position. He was sent over to run things at Darlinghurst Station in 1927.

  William Mackay was every bit the Glaswegian. Despite having been in the NSW Police Force for more than twenty years, he sounded like he had just stepped off the boat. He also carried with him some of that bulky Highland heritage that had flowed into Glasgow in the previous century. He was tall and broad, and was known to smash down doors. Mackay had no time for any leniency in fighting the thugs around eastern Sydney. Preferring surveillance and undercover tactics, he was a man on the make and wanted to use the razor wars to further his aspirations within the force.

  Mackay also knew how to frustrate the crooks and block their regular business in sly grog, drugs and sex. Kate Leigh had many ‘sharp-eyed cockatoos’ who would stand in front of or near her houses and shops, looking out for police. Mackay pushed Leigh out of the main area of Darlinghurst with sheer persistence. The inspector instructed two constables to regularly patrol the street in front of Kate’s biggest sly-grog shop, where she was also peddling drugs. They walked up and down the street, stopping in front of Leigh’s place and talking for a long time, before walking back up the street. This would go on for hours. Leigh complained to her friends in local politics and they contacted the commissioner. Mackay was crafty. He claimed Kate’s life was in danger and argued, ‘It is my obligation to see that the threat of murder is not carried out. I intend to keep her premises under continuous surveillance so long as she is in my district.’ Mackay won and Leigh moved her business into Surry Hills.

  Violence again erupted in May 1929. It went down in history as the ‘Battle of Blood Alley’. In Eaton Avenue, Kings Cross, over the course of about half an hour, a violent brawl broke out between Phil Jeffs’ gang and rival gang members. Locals watched in horror as the punches flew and blood spattered across the ground. Bodies were flung in all directions. Razors, guns, fists and feet collided in the bloody showdown. Jeffs had had it coming for a long time. He had been cutting cocaine with boracic acid and ripping off his many customers. Word got around and both the dealers and users were unhappy. They wanted Jeffs’ blood. When the police arrived around 10.30 pm, everyone was wearing the wounds of one of the most violent brawls the city had ever seen.

  Just when the police thought ‘Blood Alley’ might have settled the score for a while, violence erupted again in July. Some of Kate Leigh’s men ambushed members of Devine’s gang in the ’Loo. The violence continued out to Maroubra, where Big Jim Devine shot at Leigh associates outside his house. Kate’s close friend, bodyguard and lover, Walter ‘Wally’ Tomlinson, was injured and Gregory Gaffney was shot dead. Jim Devine was later found not guilty at his trial. It didn’t help the police case that no one in the underworld was willing to give any information about exactly what had happened.

  Another battle caught the police off guard yet again in August. The ‘Battle of Kellett Street’, once again in the Cross, saw Leigh’s and Devine’s gang members fight it out for control of cocaine and booze in eastern Sydney. Bottles and rocks flew about the place and the 40-strong brawling group took to one another with guns and razors. More than a dozen injured men were lying about the street when police turned up. Not one soul would identify his assailants.

  The corner of Crown and William streets was the scene of more violence on 9 November 1929. This time, Wally Tomlinson was shot through the chest and arm. His mate, former rugby league footballer Barney Dalton, fared far worse, dying from a bullet wound to the heart. The pair had just stepped out of the Strand pub after six o’clock closing with another friend, Edward Brady. It was a known underworld haunt and a favourite of Tomlinson’s when he wasn’t getting sly grog from Kate. The shooting was described dramatically in the local papers:

  An instant later several shots were fired. Dalton clutched at his breast, wavered to and fro on his feet, and collapsed slowly to the pavement. A pool of blood slowly formed about his fallen body. The horrified onlookers then saw Tomlinson stagger back with a crimson stain on the centre of his shirt, while the third man, Brady, looked at his hand in amazement. ‘I’m hurt,’ he said.

  Barney took his last breath only minutes after arriving at St Vincent’s Hospital, before police could cajole any information out of him. Wally Tomlinson wasn’t talking to anyone, least of all the police. Thomas Kelly, the man who had driven the injured men to the hospital, told reporters that locals had witnessed the shooting and a crowd of 200 people was there
by the time he drove off.

  No one was talking. As much as they all hated each other, no crook was willing to give up even their enemies to the police. The only law they adhered to was the one decided in the streets, back alleys and grog shops. There was no question about the cause of the violence. As the Sydney Morning Herald reported shortly after: ‘The police are convinced that the shooting marks another stage in the long drawn-out vendetta between rival underworld gangs, a vendetta which has been marked at intervals by many desperate shooting affrays.’

  The rivalry between the leading gangs and their members was common knowledge. It was clear that Kate Leigh was on the back foot and the Devines had gained much ground in the previous months. The papers described the situation for an anxious Sydney public:

  Until three months ago there were three notorious underworld gangs, one of which was stronger than the other two combined. Since then there has been a fusion of forces, and there now are only two gangs. The leading figures of the two gangs are known as ‘dead shots.’ It is whispered in Surry Hills that the gang which has suffered most casualties in recent duels intends to concentrate upon shooting the formidable leader of the rival gang and his wife. This man, who is middle aged, but of massive build and of great strength, is feared as an accurate marksman with either revolver or gun. His wife, who is of very attractive appearance, has a long police history. She, also, is known as an expert with a revolver.

  Wally Tomlinson’s injuries were severe enough to place him in a critical condition in hospital. In the belief that he was dying, Tomlinson gave a deposition to police and named Frank Green as one of the shooters. He also named Jim Devine, Tilly’s husband. Edward Brady, recovering from the bullet wound to his hand, refused to name his attacker. At the January inquest into Dalton’s death, however, Wally Tomlinson changed his mind. He had survived the shooting and was now more intent on self-preservation. He claimed he hadn’t seen Devine there and Tilly’s husband went free. Frank Green was later acquitted of Dalton’s murder in June 1930, but the judge pleaded with Green and his supporters in the courtroom to end the vendetta.

  Frank Green was furious that Wally had named him in his earlier evidence, and the newspapers predicted, rightfully, that he was a marked man. But it wasn’t just Wally who had to watch out. Green told Justice James: ‘I do not know why Tomlinson has given this evidence against me … I do not think he knows himself, unless it is because of a woman – a woman with whom he has lived … a woman who hates me – Kate Leigh.’

  John ‘Snowy’ Prendergast, a migrant from Victoria, wanted revenge. He was out to get Tomlinson for naming Frank Green as the man who murdered Barney Dalton. A cocaine addict who began his criminal career as a thief in Manly, Prendergast was high when he tried to raid Kate Leigh’s Riley Street shop in the early hours of the morning of 27 March 1930. Kate was having none of it. Prendergast continued with his threats to find and harm Wally. Kate returned with a gun and shot him in the stomach. There was no denying what had happened. Kate Leigh had shot a man dead. Truth newspaper followed the events closely:

  … once again in Sydney the hatred of the members of the underworld has burst forth in all its viciousness, and another man lies dead; his life blood oozed out through a rifle bullet wound in his stomach. Although the shooting is associated with well-known members of the underworld, police are reticent about discussing the details, but the feature of paramount interest is that Mrs. Kate Barry, better known as Kate Leigh, is charged with the shooting. The murdered man is John William Prendergast, aged about 26, and he was picked up in a dying condition by a policeman in a Woolloomooloo lane on Thursday morning.

  Two weeks later, Kate arrived at the Coroner’s Court in George Street in a large Studebaker sedan. Leigh remained strong in the face of reprisals. Outside the court she told reporters: ‘I’m not afraid of any of that bunch.’ According to Kate’s version of events, she was awakened early on the morning of 27 March by the shouts of men outside her house. Looking out, she saw Snowy Prendergast, his brother and other men. Snowy wanted Wally Tomlinson and told Kate to ‘fetch him out’, to which she responded by warning him she had a gun and wasn’t afraid to use it if they broke in. Kate Leigh then described the shooting:

  They then said they would kill him and me, too. I told them that if they came in, they did so at their own risk, and I saw some of them disappear round the back of the house. A few minutes later Eileen Wilson, who lives with me, called out that the men were bashing in the back door … I picked up my gun and ran downstairs and saw my wardrobe thrown face down and smashed open. John Prendergast was standing on the fallen wardrobe, and I said, to him, ‘If you come another inch I will shoot you’… A man handed John Prendergast a brick through the window, and Prendergast threw it at me … It hit the electric light … I then told Prendergast that if he came another step I would shoot him. As he went to step forward I shot at him.

  Kate claimed she had meant to shoot Prendergast in the legs and had not meant to kill him. She feared for her life and had defended herself. Kate Leigh was found not guilty of Prendergast’s murder. The Coroner, finding that Prendergast had died from a bullet wound to the stomach, ruled the shooting ‘justifiable’ on the grounds that Kate believed her life was endangered.

  Despite the not guilty verdict, Kate Leigh was ridiculed in the newspapers. Truth was particularly scathing, arguing later in 1930 that she should have been in gaol. The paper was unconvinced by Kate’s pleas that she was a good person:

  It is a strange world when that vicious old harridan, Kate Barry, wishes to pose in it as a woman with a generous heart. But unbelievable though it may seem, that was this notorious woman’s dearest wish – to be understood as a free and easy Lady Bountiful of the underworld … Around her drifted the worst people of the city … battered derelicts whom she rescued from the gutter and starvation, but not from crime. If they would not pursue a life of crime they could, and did, stay starving in the gutter as far as Kate Barry was concerned.

  Frank Green didn’t live much longer than his former lover and ‘pretty girl’ of the underworld, Nellie Cameron. By the 1950s he was living in a shabby place in Paddington and regularly argued with his lover, Beatrice Haggett. Frank drank heavily, and on the night of 26 April 1956 he and Beatrice had an argument over his constant nagging and accusations she was having an affair. Beatrice drove a carving knife into Frank’s chest, just below the collarbone. He died shortly after. Quizzed about whether she would attend Frank Green’s funeral, Kate laughed and told reporters she had no intention of going but would happily ‘dance on the bludger’s grave’.

  Wally Tomlinson didn’t stick around in eastern Sydney past the razor wars. His run-in with Green and Devine had rattled his confidence, and he decided to give up his work with Kate Leigh. Tomlinson had been close to Kate in the years after Teddy Barry took off to Fremantle, but their personal and business relationship had run its course by the early 1930s. By that stage Kate had moved Jack Baker in as her business partner and de facto. He, like Tomlinson, had to hold his own against Kate and match her toughness.

  In the heyday of underworld violence, Leigh was far from being the matriarch she later became in eastern Sydney. Truth declared in October 1930 that she was ‘bad through and through. She was the worst woman in Sydney. Her depravity was deeper than that of the lowest woman in her houses of ill-fame.’

  The violence continued even after Prendergast’s death:

  Early yesterday morning William Rogers, alias William Roy Elmer, alias William Roy Williamson, 36, gasped out his life in Sydney Hospital, after being fatally wounded down in Palmer-street, where he was shot through the left side, on Good Friday afternoon. Another man, named Charles Burke, friend of Eileen Leigh, daughter of the notorious Kate Leigh (or Barry), lies in St. Vincent’s Hospital, suffering from a bullet wound in the back.

  Before he died, William Rogers claimed he didn’t know who had shot him. This was one of the hardest parts of the violence for police. Underworld silence was stron
g.

  At the height of her criminal career in the late 1920s and 1930s, a time when the authorities were trying to tackle the problem of gangs controlling drink, drugs and prostitution in the city, Kate Leigh faced greater scrutiny of her illegal activities. A special vice unit of the NSW Police was created to deal with sly-grogging, and new consorting laws made it an offence to associate with known criminals and ‘bad characters’. Kate Leigh found this out in June 1929, when she was arrested for being in a house frequented by thieves and sentenced to four months’ imprisonment at Long Bay. The consorting laws impacted on her activities and she regularly faced court for associating with other criminals. In January 1932 she was sentenced to six months’ imprisonment for ‘habitually consorting with women of ill repute’.

  Prison didn’t prove as much of a deterrent for Kate as the police and magistrates might have hoped. In February 1931, Truth ran a lengthy article on Kate Leigh’s domination of the women’s section of Long Bay. Serving time for selling cocaine, Leigh had apparently established a ‘reign of terror’ within the prison. She was afforded any number of comforts, and continued running her outside empire. Inside the prison she worked in the kitchen and controlled it like a head chef. Any woman who did not abide by her rules or got on the wrong side of her was bundled off to another part of the gaol. Some exprisoners told the press they had never served as hard a time inside as they did under Kate. She ruled the women’s section like it was her criminal business back in Surry Hills: ‘One woman – who owes her imprisonment directly to her association with the notorious gangstress – recently had a visitor who brought a parcel of sweets and delicacies from her admirers at-liberty. The parcel was just being handed over – so the story goes – and Kate swooped on it.’