FLEMINGTON racecourse once again becomes host to Australia's biggest week-long party this weekend, but Sunday night's shooting at the house of Racing Victoria's chief steward, Terry Bailey, is a reminder that the sport of kings is also the sport of crims.

RICHARD BAKER reports for FAIRFAX MEDIA that the euphemism "colourful racing identity" exists for a very good reason. Racing in Australia has always been irresistible to rogues – including those with a genuine passion for the sport – because it offers them ample opportunity to make fresh money and launder the dirty cash they've made elsewhere.

Racing Victoria's chief steward Terry Bailey outside his house after shots where fired at his front door. Photo: Joe Armao

Over a century ago, one of Melbourne's most notorious gangsters Squizzy Taylor tried his hand at being an apprentice jockey before he was busted pick-pocketing the watch and chain of a man at the Ballarat racecourse. He was jailed for two years in 1908.

During the 1922 Caulfield Cup carnival, the diminutive gangster was ordered off the course by racing officials who deemed him an undesirable person, according to Taylor biographer Hugh Anderson. Hours later, in the dark of night, the members' stand at Caulfield was found ablaze. Taylor was a suspect but no evidence was found to connect him to the fire.

Author Frank Hardy tied Taylor to Melbourne powerbroker John Wren in his famous 1950 novel, Power Without Glory, a piece of work that saw Hardy unsuccessfully prosecuted in Victoria's last case of criminal libel. Wren's influence, Hardy claimed, was able to shield Taylor for a time.

Jockey Danny Nikolic Photo: Pat Scala

Wren's involvement with racing went back to the 1890s, when he ran an illegal betting operation from the back of a Collingwood shop. The venture made him a rich man who was able to wield influence – which allegedly involved bribery, according to Hardy – in politics, religion and Victorian football. In 1903, Wren's horse Murmur won the Caulfield Cup.

In Sydney throughout the 1970s and 1980s, high-flying bookmaker George Freeman was the perfect embodiment of the moniker "colourful racing identity". Though he was only ever convicted of theft and minor illegal betting offences, Freeman was named in several royal commissions and state parliament as an "organised crime" figure allegedly involved in far more serious matters such as bribery and drugs.

In more recent times, it has been Melbourne's major drug dealers who have had a deep and corrosive involvement in racing.

Tony's brother Horty Mokbel. Photo: Andrew De La Rue

Jailed drug kingpin Tony Mokbel is perhaps the most infamous modern-day example. Mokbel, his brother and convicted drug trafficker Horty Mokbel and others were part of the "Mokbel syndicate", which owned several top racehorses during the 1990s and 2000s.

These horses, bought with the proceeds of their expanding drug empire, gave the Mokbels access to top trainers and jockeys. Banned jockey Danny Nikolic was warned by racing stewards against getting too close to the Mokbel syndicate after riding at least five of its horses.

Nikolic, who has been banned from riding since making threats to Bailey in 2012, has also been banned by police from Crown Casino. A recent police ban preventing him from walking on to any Victorian racecourse was recently overturned by the Victorian Supreme Court.

Drug kingpin Tony Mokbel. Photo: Andrew De La Rue

Two-time Melbourne Cup-winning jockey Jim Cassidy was another who was deeply involved with Tony Mokbel. In the late 1990s, after returning from a ban for tipping about horses he was riding, Cassidy started passing information about his mounts to the Mokbel syndicate in return for cash.

The Mokbel syndicate used racing to launder drug proceeds through bookmakers. Despite regular big losses, just one win could give Mokbel what he desperately craved; an apparently legitimate profit.

While Tony Mokbel is said to maintain a keen interest in racing from inside prison, Horty Mokbel recently made headlines after being exposed as using online gambling agency Betfair to shift millions of dollars in suspect funds. Horty has been banned from race tracks and Crown Casino since 2004.

Racing Victoria last year charged another man associated with the Mokbels, racehorse owner and convicted cocaine supplier Joe Zaiter, for failing to declare his criminal record and making false statements to stewards.

Zaiter became associated with the Mokbel syndicate in 2007 after failed punters' club operator Bill Vlahos sold him a stake in the $1.8 million horse Pillar of Hercules. The horse was being auctioned after its ownership links to the Mokbels was exposed.

Another prominent drug trafficker, Rob Karam, who is spending the best part of the next 20 years in jail for his part in the world's largest attempted ecstasy importation, was also a former owner of several race horses.

There is also still the unsolved 2011 murder of racing trainer Les Samba in Middle Park in Melbourne, which police believe may involve a $200,000 debt owed to a NSW drug syndicate. The investigation into Samba's death unwittingly led to a race fixing probe involving leading jockeys known as "The Smoking Aces" affair.

Fairfax Media is not suggesting anyone referred to in this article was involved in the shooting at Bailey's home in Melbourne's east.

For all the fun, entertainment, jobs and glamour that racing provides Victorians, Bailey knows better than most just how hard it is to eradicate its dark side.