Bernard Hugh Dalton steps out of Sharland’s Strand Hotel, Woolloomooloo into the warm evening air of 9 November 1929. The shadows are beginning to creep along the footpaths as the sun starts its journey toward the horizon.
Alongside Dalton are his associates, Walter Tomlinson and Edward Brady. All three men are members of the fearsome Kate Leigh razor gang.
Dalton, better known as “Barney”, was broad shouldered and still cut an athletic figure from his rugby league playing days.
He carried a reputation for brutality and served as Leigh’s bodyguard and cocaine supplier.
On this particular evening he barely starts up the street outside the hotel before a short, angry man, who appears to be waiting for the trio shouts “cop this you bastard”, and fires five shots.
Barney is hit square in the chest, dropping him to the pavement. As Tomlinson tries to help his fallen friend, he’s hit twice, once in the chest and once in the arm. Brady is hit in the hand.
The stout gunman in a fedora with a distinguishing L shaped scar on his right cheek takes off, tossing his smoking revolver into a backyard on Palmer Street and disappearing back into Sydney’s underworld.
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Drinking with the group at the time was Tom Kelly who bundles Tomlinson and Barney into his car, rushing them to St. Vincent’s Hospital. Kelly barely pulls away from the curb when Barney breathes his last breath.
At that moment, the chapter is closed on rugby league’s most terrifying figure. The two time premiership winner with Eastern Suburbs, who infamously committed crimes in his old playing jersey is dead at the age of 39.
Dalton wasn’t the target of the hit, but he was the one who paid the ultimate price, leaving behind his wife Bertha of 13 years who was packing for a holiday when he was killed.
Barney Dalton wasn’t always a fearsome standover man working for one of Sydney’s cut throat razor gangs.
He was originally a rugby league pioneer, named as the 43rd player to represent Eastern Suburbs when he debuted for the club in 1910.
Dalton was a member of the Easts side that won its maiden premiership in 1911, and its second in 1912. He took a year off in 1913.
Much like many of today’s players, Barney also dabbled in boxing and was known to frequent Pat Keiran’s gym, sparring fighters.
That would have come as little surprise to his teammates and opponents as a 1912 match report from the Sydney Sportsman highlighted an on-field fight between Dalton and South Sydney’s Owen McCarthy.
Despite Dalton being a back and McCarthy a second-rower, the pair stood toe-to-toe and engaged in a brawl that eventually saw them dismissed from the field.
He returned to rugby league in 1914, winning City Cups with Easts that year and in 1915.
The lanky winger scored 16 tries in 61 matches for the tricolours, but at the age of just 23 he walked away from the game.
He played alongside older brother William “Billy” Dalton during 1911 and 1912 before Bill completed his career with Glebe in 1914.
1920s Sydney was a fairly brutal and bloody place to be. Infamous razor gangs roamed the streets as underworld queens Kate Leigh and Tilly Devine fought for control.
The cut throat razor had become the weapon of choice after New South Wales outlawed the possession of firearms without a permit.
Gangsters would routinely interact with police, so they could explain away a razor, even when those razors were used to brutally disfigure both men and women.
On the same weekend that Dalton was murdered, 10 other violent crimes occurred in Sydney.
On the Thursday before the shooting, a man by the name of James Wilson was slashed with a razor in the CBD. On Friday Isadore Van Whye was slashed and kicked in Surry Hills while Ettie Murray had acid thrown in her face also in Surry Hills.
On the day of Dalton’s shooting, Grace Fraser was shot in the back in Surry Hills, James Paxton was attacked by a gang in Miller’s Point, Leslie Smith was attacked by a gang at Bankstown and on the Monday Armande John Mefrett was slashed in Newtown.
While the murder of the former Eastern Suburbs winger attracted the majority of the media coverage, a violent crime on the streets of Sydney certainly wasn’t out of the ordinary.
Driving much of this violence was an underworld war between Kate Leigh and Tilly Devine.
Leigh headed brothels, speak-easies, illegal bookmaking and trafficked cocaine. Devine too was involved in the same industries and the pair faced off, vying for dominance during the 1920s and 1930s.
The pair were exceedingly wealthy through the illegal activities and in order to keep everything running, they employed male gangsters as enforcers.
The Leigh and Devine gangs were involved in pitched street brawls in Eaton Avenue and Kellett Street, King’s Cross in May and August 1929.
Gangsters would attack opposing cocaine sellers and prostitutes with straight bladed razors to impact their profits.
Leigh’s husband through most of the 1920s was one of her bodyguards and notorious standover man Walter Tomlinson. At the age of 16 he had already been charged with Shooting At, With Intent To Murder. By the late 20s he was a hardened criminal.
Devine’s husband at the time was accused murderer, convicted thief and gangster Jim Devine. He was involved in high profile murders across 1929-1931 and was charged as an accessory in the murder of Barney Dalton.
Reports from after his death along with state records reveal that Dalton was an electrician who worked for the City Council and was married in 1916.
It’s not entirely clear when Dalton joined Kate Leigh’s gang but a column that appeared in newspaper The Labor Daily in 1929 following his death stated that “Dalton was feared by gangs”. He’d earned a reputation for defending small bookmakers and successful punters at race tracks.
It was reported at the time that racecourse gangs would target the smaller bookmakers or individual punters and ask for a dollar. If they refused, the gangs would simply say “We’ll see you outside”.
This usually resulted in the victim being attacked, sometimes with a razor, and the police being unable to pursue those responsible as no one wished to testify.
Dalton was approached by those bookmakers and punters for protection and had a tough enough reputation that he’d tell the gangs to let up, and if they didn’t “he would take a hand”.
According to the columnist, most of these racecourse gangs took the warning and stayed away from anyone associated with Dalton.
A report in The Sydney Morning Herald in 1924 stated he was arrested and charged with using indecent language and for being in possession of a revolver without a licence.
The gun had fallen out of his pocket when he was doing cartwheels as a linesman for a local football match.
It’s likely that he was a member of Kate Leigh’s gang before this incident given he would have otherwise had no need to be carrying an illegal firearm.
1929 was very much the bloodiest period of the Sydney razor gang wars. While there had been plenty of street violence throughout the early parts of the decade, 1929 saw multiple high profile murders as the two gangs vied for dominance.
A more minor player in the underworld at the time, Phil Jeffs had been involved in a brawl on 7 May 1929. He was shot but recovered and went underground, resurfacing later in the 1930s as Leigh and Devine’s power waned due to increasing police pressure.
But the May brawl and shooting was merely the start. On 17 July 1929 a group of Kate Leigh’s men led by gangster Gregory Gaffney ambushed Devine associates Frank Green and Sid McDonald.
Green was wounded and taken to the Devine’s Maroubra home. A second attack that same night, on the home involving Walter Tomlinson and Dalton resulted in the death of Greg Gaffney, shot by Jim Devine. While he was charged with murder, he was acquitted on the grounds of self defence.
Green, after going to Sydney Hospital, refused to tell police who had shot him.
On the 8 August that same year Devine went on the offensive, attacking Leigh’s sly-grog establishments in a pitched battle while her opponent was in jail.
This brings the story to 9 November 1929.
It’s believed the plan was for Green to murder Tomlinson as revenge for the attack on the Devine group back in July. Dalton just happened to be collateral damage.
In a rare breaking of the gangland omerta, Tomlinson, from his hospital bed named Green as the attacker. It was on this basis that police formed their case and charged both Green and Jim Devine with the murder of Barney Dalton.
Police though withdrew the charges against Devine, proceeding with their case against Green and taking it to trial.
At trial, Tomlinson stuck to his story, however denied any knowledge or involvement in the underworld, claiming he didn’t know who Kate Leigh was.
Police alleged that a constable had overheard Green, while undergoing prison transport, say to another prisoner, “The bastard (Tomlinson) picked me today, he never hesitated. It’s a pity I did not get him as well as Dalton while I was about it.”
The defence brought forward a number of witnesses, including Edward James Brady who was also shot during the attack, with none of them labelling Green as the offender.
Another witness, Charles Connors, claimed he hadn’t seen Green anywhere near the hotel when the shooting occurred. He also stated that Tomlinson was shot first before Dalton stepped into the line of fire. On cross examination he revealed he had been slashed by a razor six years earlier, with the prosecution hinting it was Green who had done it, although Connors didn’t confirm it.
Dalton’s widow however, stated that Connors had told her that Green had shot her husband.
Even with an eye witness, a gun and a suspect with both a motive and the criminal history to carry out the attack, Frank Green was not convicted due to the jury being deadlocked.
A second trial saw him acquitted.
Green, despite his violent history and long list of enemies, would survive into the 1950s yet still meet a brutal end. He would be found dead in 1956 at his home after his partner stabbed him with a kitchen knife in self defence.
Barney Dalton’s funeral was held at St Mary’s Cathedral, Sydney before he was buried at Botany Catholic Cemetery which is today known as Eastern Suburbs Memorial park.
His funeral was attended by 200 people with women openly mourning his death.
His wife maintained he wasn’t a gang member, but was a good man with the couple set to embark on a fishing trip the day he was murdered.
Dalton, though, was known throughout the underworld. He guarded grog shops, was Leigh’s bodyguard and sold cocaine for her among the usual things an enforcer does including doling out beatings, slashings and shootings.
Larry Writer, author of the book Razor, Tilly Devine, Kate Leigh and the razor gangs, once said that Dalton often committed crimes wearing his old Eastern Suburbs jumper.
The former Rooster became more of a celebrity in his underworld career than he did as a premiership winner for Eastern Suburbs.
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