Sydney's Boxing & Gambling Roots

Sydney's Boxing & Gambling Roots were built on Feuds and Frontier Life in 19th-Century Ku-ring-gai

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Picture today’s Killara, Gordon, Pymble and St Ives: a serene, upscale haven on Sydney’s North Shore, with elegant estates and tree-lined streets. But rewind to the nineteenth century and this slice of Ku-ring-gai — then referred to as the Parish of Gordon — was a rugged frontier pulsing with vice and violence. It was an “honour society” akin to the antebellum South, where reputations were forged in blood, bets, and bare knuckles. At the epicentre of Sydney's Boxing & Gambling roots stood the pubs, dens of hard drinking, cockfighting, gambling, and brutal brawls.

Leading the charge was the Waterhouse clan, a dynasty of frontier sportsmen whose Green Gate Inn became legendary for hosting world-famous boxing matches and fuelling decades-long rivalries. None burned hotter than their feud with the McMahon family, owners of the rival Travellers Rest Inn. And the pinnacle? The epic 1861 clash between Tommy Waterhouse and “Flash” Bourke — a blood-soaked showdown that put this part of Sydney on the sportsman’s map.

Into this wild Parish of Gordon stepped the Waterhouses, further elevating its reputation as a hotbed of sport and strife (see 2075 Issue #11, Nov 24). Thomas Waterhouse, great-great-grandfather of the famous bookmaker Robbie Waterhouse, acquired the Green Gate Inn in 1853. It sat on a sprawling estate along the old Lane Cove Road (today the Pacific Highway, Killara), serving timber workers, farmers, and travellers. Thomas, a charismatic father of 13, embodied the frontier spirit: a lover of horse racing, rowing, cockfighting, and boxing. His inn was not just a watering hole; it was the stage for vice-fuelled spectacles that drew crowds from across the colony.

Not just boxing, gambling was everywhere

Horse racing kicked up dust on the Lane Cove Road outside the Green Gate, with families like the McIntoshes and McMahons entering steeds in high-stakes gambles. But boxing was the clan’s true claim to fame. Bare-knuckle prize fights — illegal yet irresistible — turned the inn into one of Australia’s premier pugilistic establishments, known by sporting men across the colony and as far as London and San Francisco. Thomas Waterhouse Jr., or Tommy, emerged as a star: intelligent, gentle off the canvas, but a demon with his fists. In 1857, Waterhouse’s licence was nearly revoked after a brawl involving his sons, but glowing references saved the day. That year, Tommy’s legend ignited when toughs from The Rocks crossed the harbour and refused to pay their tab at the Green Gate. The Rocks larrikins got heavy, but Tommy taught them a painful lesson and sent them running for the next ferry back to Dawes Point, banning them from the North Shore forever.

The Waterhouse clan became legendary in barrooms, billiards saloons, and gymnasiums far and wide as Tommy’s boxing prowess shone in a string of infamous bouts in reserves along the Lane Cove River. In April 1857, Tommy faced Bill McMahon — son of rival publican Owen McMahon — in a gruelling 117-round epic, winning on a technical knockout for a £15 prize. It was a taste of the family feud to come. In May 1858, he drew with Walter “The Oysterman” Kimber after five rounds, the bout marred when Kimber struck Tommy while he was down. Later came the 1866 clash with James Kelly, ending in a sunset draw; Kelly’s crew then stormed the ring, but were repelled by locals. As they fled by boat, Lane Cove lads pelted them with rocks and bottles.

The rivalry that captured the community

But no fight captured the era’s wild essence like Tommy Waterhouse vs “Flash” Bourke in 1861 — the “Championship of the Colony,” with £100 on the line. Bourke, a one-eyed Irish brawler from Victoria, challenged Sydney’s best. Tommy accepted, locals wagering 100 guineas on their champ. Prize-fighting was banned, so secrecy shrouded the event—until it didn’t. Hundreds chartered steamers across the harbour, converging on the Green Gate Inn.

Bourke’s team was based at Owen McMahon’s Travellers Rest Inn in Gordon, a deliberate jab amid the raging Waterhouse–McMahon feud. Sparked by a £5 horse bet in 1852 (McMahon’s Pretty Boy vs Waterhouse’s Jack), the rivalry had exploded into violence. On 7 April 1855, Thomas Sr and Owen brawled on Lane Cove Road. The McMahons, allied against the Waterhouse–McIntosh bloc, hosted Bourke to spite their foes — Owen’s son Bill had already fallen to Tommy in the ring.

The initial ring went up in a bush clearing—now genteel Killara Park. At 3:30 p.m., as Bourke strutted in, police stormed the scene. Inspector Ryland, pistol cocked, vowed to “blow out the brains” of any who resisted, and seized the ropes. Undaunted, the mob trekked six miles through scrub to Pearce’s Corner in Wahroonga. Bourke entered flashy; Tommy, humble. For two hours, they traded savage blows — Bourke swinging wild, Tommy agile and precise. Blood soaked the ground; Tommy slipped in the gore, lacking studded boots. Bourke gasped, “You’re a lot better than I thought.” As sunset loomed, Bourke went blind in his good eye; Tommy was too spent for a knockout. They postponed till dawn.

Bourke retreated to the Travellers Rest for leech treatments; Tommy to the Green Gate. Morning came, but the referee vanished — so a draw was declared. The saga elevated the Waterhouses and their inn to legendary status, with tales spreading worldwide. Fights proliferated in Killara Park, cementing Sydney as a global boxing hub alongside London and San Francisco.

The McMahon feud simmered on, part of Gordon’s honour-bound vendettas. Other clans had clashed—McIntoshes vs Cooks in 1836 over a seduction, settled for £500; Matthews attempted to shoot his brother-in-law in 1846. But Waterhouse vs McMahon divided the community for decades—brawls, beatings, duels. One McMahon even assaulted Peter Jackson — a boxer mentored by the Waterhouses and the son of a Caribbean slave. Hired as a sawyer in 1880, Jackson trained under Tommy at the Green Gate Inn, going unbeaten locally before claiming the British Empire heavyweight title. Racism denied him the world crown, though he is considered by some to be the greatest boxer to have lived.

The Kelly rivalry added fuel: after the 1866 draw, the Kellys ambushed the Waterhouses at Dearing’s Wharf in 1867, knocking Tommy out with a rock. Pubs amplified these clashes—the Green Gate vs the Travellers Rest. Even the 1862 Green Gate murder reeked of feud: Pymble resident Andrew Bromley, a Waterhouse ally fighting a massive bushfire, was stabbed, his throat slit, and his body dumped in a well. Suspicions pointed to McMahon ties, but the case went cold.

By the century’s end, railways and suburbanisation civilised the Parish, rebranding Killara, Gordon, and St Ives as a “gentleman’s suburb.” Yet the Waterhouse clan—pioneers in hospitality, fruit, horse racing, and fighting—shaped Australian culture. They challenged racism through Jackson, built boxing’s legacy, and embodied the wild larrikin spirit. Amid feuds like the McMahon saga, they turned frontier chaos into enduring foundations. The Greengate Hotel, as it would later be known, has not been in Waterhouse's possession for almost 120 years, though the 193-year-old establishment still stands strong.