While today we’re 10 craft beers deep into the age of boutique hotels, once upon a time, Sydney’s pubs were much wilder places.

Here are some familiar watering holes with a chequered past.

IRON DUKE

220 Botany Rd, Alexandria

In the 1980s, the Iron Duke had a reputation for bikies, strippers and bar fights. Owned by convicted heroin trafficker Neddy Smith, it was rumoured to have been where robber Frank “Baldy” Blair was tortured and his testicles blow-torched before being tossed into the harbour.

But it was the attempted murder of Smith himself on April 2, 1986, that made headlines. Smith was on the footpath outside when ex-boxer Terry Ball mounted the kerb and ran him over, reversing over him again and breaking multiple bones. Ball was charged with attempted murder but when the matter went to court, Smith said the cops had the wrong man, despite the fact that three years earlier gangster Abo Henry, apparently on Smith’s behalf, had shot Ball in the head.

A year later, after a drinking session with crooked cop Roger Rogerson at the Coogee Hotel, Smith stabbed a stranger to death over a road rage incident outside the hotel. He was jailed for life.

HOTEL ASTRA

34 Campbell Pde, Bondi (now the Astra Retirement Village)

During WWII, the Astra was famous for its long bar and pies for which people would drive miles. But in February 1943 it gained national notoriety for an enormous brawl involving 1500 men. It was a Saturday with no horse racing so more beer was drunk than usual and when the beer ran out at 5.45pm, all hell broke loose.

Police arrived to restore order, glasses were hurled and men trampled. A tram attempting to pass through the crowd outside ran over one Herbert Loveridge of Erskineville, who was dragged down the road. He was saved when the crowd lifted the tram off the rails to release him.

KOOKABURRA HOTEL

41 Canley Vale Rd, Canley Vale

In March 2000, the Kookaburra Hotel was the scene of a brazen hit on Ngia Doan, who was linked to the 5T Vietnamese crime gang. Four Asian men walked into the hotel, fired several rounds at the young man then calmly departed in a taxi. The offenders were met by police at an address in Coolibah St, Canley Heights, and a dramatic standoff followed. The hit was the culmination of years of gang violence that had plagued the western suburbs after the 5T gang began to implode. The 5Ts had dominated Sydney’s heroin trade in the 1990s but in 1995, leader Tri Minh Tran was assassinated, splitting the gang and sparking an escalation of violence that led to its eventual demise.

VIKING TAVERN

Now The Mill Hotel, 189 Beaconsfield St, Milperra

Before a makeover put the ghosts of the past to rest, this was the battlefield of Australia’s most deadly bikie war in 1984. Known as the Father’s Day massacre, seven people were killed, including a 14-year-old bystander, and 28 injured when warring gang members fought in the carpark.

Tensions were at boiling point after members of the Comanchero Motorcycle Club walked away from their brotherhood and patched over to the first Australian chapter of the Bandidos. The massacre captivated the nation, made headlines across the globe, and led to 31 people being tried for murder.

THE ROSE HOTEL

1 Swanson St, Erskineville

The Rose was the scene of one of Sydney’s wildest pub brawls in 1942 after a group of US servicemen strolled into the bar bragging about finding women. Unfortunately for them, a group of battle-hardened diggers were enjoying a quiet drink at the time, an argument broke out and the Yanks copped a thrashing. Word went out and US servicemen flooded the Rose looking for revenge. The diggers did likewise and a violent brawl ensued. Hundreds of locals watched on until military police arrived to break up the melee. Blood-streaked soldiers and sailors were dragged into waiting paddy wagons and ambulances. The diggers, going on the count of injured, won the day.

THE STRAND HOTEL

99 William St, Darlinghurst

In the late 1920s, Darlo and Surry Hills were a cesspit of crime and prostitution and the razor gang wars raged between brothel madam Tilly Devine and sly grogger Kate Leigh.

Frank Green, a small homicidal cocaine addict, who was for a time the main “muscle” in Devine’s gang, murdered rival gunman Barney Dalton outside the pub on November 9, 1929.

Shouting “Cop this you bastard”, Green fired his long-barrelled revolver three times, killing Dalton and badly wounding his mate Wally Tomlinson.

Gasping in the gutter, Tomlinson dared Green to have another go. He obliged and shot him in the chest. Tomlinson survived.

EMPIRE HOTEL

32 Darlinghurst Rd, Kings Cross

Before it became the Empire Hotel, it was the Carousel Cabaret, a nightclub owned by Sydney crime boss Abe “Mr Sin” Saffron and the scene of one of Sydney’s most enduring mysteries. The Carousel was the last place newspaper publisher and heiress Juanita Nielsen was seen alive before she vanished in 1975. Many believed Saffron was behind her death; her opposition to high-rise development in Kings Cross and the razing of terraces in Victoria Rd put her in the way of Saffron’s schemes. Invited to the club on the premise of selling a newspaper ad, she was never seen again. Saffron’s long-serving deputy James McCartney Anderson, who managed the club, and night manager Eddie Trigg, were later convicted of conspiring to kidnap Nielsen but her body has never been found.

LANSDOWNE HOTEL

6 City Rd, Chippendale

In the 1930s, Kate Leigh’s standover men, including murderous thug Chow Hayes, could often be found holding up the bar at the Lansdowne, which became the scene of one of his infamous stoushes.

In 1937, Hayes had got out of prison only to find he’d been replaced by another of Leigh’s favourites, Jack Baker. Having something of an anger management problem, Hayes stormed into the pub to find his replacement, invited him outside and shot him. Baker survived and Hayes escaped conviction.

AUSTRALIAN HOTEL

100 Cumberland St, Millers Point

Ex-boxer and standover man John William “Joey” Manners, 27, was shot twice and killed outside the Australian Hotel on the evening of June 8, 1956. Two months later, an attempt was made to burn down the hotel. George Joseph Hackett, a known criminal whose day job was a painter and docker, was detained for Manners’ murder, with jealousy over a woman the alleged motive.

Hackett, who had strong links to the underworld, was acquitted after the key witness, a barman, failed to show up in court.

Three years later Hackett was shot 13 times behind a Leichhardt Hotel in Elswick St. Lennie McPherson and William “Snowy” Rayner were charged with the murder but both walked free.

NEWINGTON HOTEL

Now the Public House, 292 Stanmore Rd, Petersham

In August 1974 a cold-blooded contract killing was committed in the lounge of the Newington Inn.

Standover man John Edward “Ratty Jack” Clarke was shot in the back of the head while drinking after closing hours with the proprietor and his wife and four staff members.

The killer, believed to have hidden in the garden bar area, fired one shot which smashed through a window. Clarke, who was a known associate of criminals and on the police radar, died instantly.