Gangster Squizzy Taylor had a passion for horse racing as long as it was for nefarious purposes

Notorious gangster Squizzy Taylor was one of the many dedicated fans of racing, but after trying a career as a jockey his trackside dealings all turned crooked.

For Australians, Melbourne Cup day is the only time they have a flutter on the races. Others take it far more seriously.

Australian gangster Joseph “Squizzy” Taylor was definitely one of the latter, but he was not interested in the nobility of the “sport of kings”, the beauty of the horses, the fashion or the society aspects of racing.

He was in it for one thing — cold, hard cash. If he could not make that money actually betting on the horses then there were other angles to be worked.

Taylor (centre) died in 1927 in a gun duel with his rival Snowy Cutmore who also died.

Taylor once aspired to be a jockey and always gave out that he struggled to keep his weight down. But it is far more likely that he could not keep himself from dodgy dealings while riding. Some of his career as a racetrack jockey, pickpocket, race nobbler and arsonist is detailed in the book Gangland: This Unsporting Life by James Morton and Susanna Lobez (MUP, $29.99).

Taylor was born Joseph Theodore Leslie Taylor in Brighton, Victoria, in 1888, although he usually went by the name Leslie. Because of a squint in his left eye, his classmates called him “Squizzy”. The son of a coachmaker, or wheelwright, the diminutive Taylor had no plans to follow in his father’s footsteps, preferring to pursue a career as a jockey. At 14, he took an apprenticeship with stable owners Albert and Septimus Miller, working at Bacchus Marsh and at Mill Park. He was trained by famous jockey Bobby Lewis.

Police mugshots of the infamous Melbourne gangster. Picture. Supplied

Taylor was only 16 when he had his first winning ride on Slaten at Moonee Valley in 1904. He rode 37 winners before he got a bit greedy. In 1905 during the Newmarket Handicap at Ascot, the horse Ben Bolt, ridden by Taylor, performed so badly in the race that Taylor was called before the stewards for pulling the horse up.
He was stood down.

He had made a bit of money for fixing the race, but he now found it hard to get another ride. So he turned to a life he had already come to know.

Taylor had been a member of the “push” (a term for street gangs) known as the Bourke St Rats, which had earnt its fearsome reputation by robbing people in Melbourne’s streets. One of their favourite haunts was the Theatre Royal on Bourke St where they cornered cashed-up patrons and quickly disappeared down alleyways like rats if the police were alerted.

Taylor in police mugshot features in the

book Gangland : This Unsporting Life.

Squizzy most likely learnt, or at least honed, his new trade of pickpocketing from them and then took it to the racetrack where he knew he would find cash.

In 1908 he was caught in the act at a track in Ballarat and spent two years in prison where he became an even more hardened criminal.

Once out of prison he graduated to worse crimes.

Quizzy was suspected of the 1913 murder of Arthur Trotter, a commercial traveller whose home was invaded by burglars. He was never arrested or charged. He is also suspected to have taken part in the Trades Hall Shooting in 1915, when three burglars had a shootout with police, killing one officer.

Caulfield racegoers watch on as a fire deliberately lit by Taylor burns down grandstand.

But in 1916 when he shot dead a cab driver in a botched attempt to use the cab as a getaway car in a robbery, he was finally arrested. Police found him at Flemington Racecourse where he had been held on a charge of “being without means”. He was identified by witnesses and sent to trial. But Taylor got to the people testifying against him and provided an alibi that he had been working for Bobby Lewis in Tasmania.

In 1922 he is believed to have torched the Members Stand at Caulfield on the night before the Caulfield Cup, possibly as revenge for having been warned off the course or possibly as some kind of attempt to stop the race being run. It went ahead.

Leslie 'Squizzy' Taylor, at court in 1922.

The gangster was played by Jared Daperis in Underbelly.

The last time Taylor was ever seen at a racetrack was in October 1927 at Richmond when he got into a fight with rival gangster John “Snowy” Cutmore. Taylor had been giving protection to a brothel in St Kilda when Cutmore came in and damaged the place, grabbing a girl at the brothel, stripping her and throwing her into the street.

Taylor was going to let Cutmore off lightly and their fight at the racecourse resulted in Cutmore being warned off for life. Taylor was already banned.

The next day Taylor was seen with two other men in a cab touring some of the pubs of Carlton before heading to Cutmore’s home.

There Taylor found Cutmore in bed suffering from a cold and shot him. But Cutmore was well enough to shoot back and both men were fatally injured.

Cutmore died in bed but Taylor staggered into the street and was taken to St Vincent’s Hospital where he died. He had run his last race.