One Monday morning in the 1960s, City Tattersalls Club financial consultant Ross Pitts was given the task of taking a David Jones shopping bag containing £15,000 to then NSW premier Bob Askin's office in Bridge Street.
"The cash was left with his secretary and the understanding was that Askin used to distribute it to the poor," Pitts says. He says the bag was delivered to Askin's office every Monday when the illegal starting price (SP) bookmakers settled at City Tattersalls' lower lounge.
The Sydney City Tattersalls club around the late 1970s.
Dozens of these vignettes from the city's colourful history are detailed in a new chronicle of City Tattersalls, On A Winner by journalist Marea Donnelly, to be launched on Tuesday by former governor-general Sir Peter Cosgrove to mark the club's 125th anniversary.
He will be joined by former prime minister Tony Abbott, South Sydney Rabbitohs legend Bob McCarthy and bookmaker Robbie Waterhouse.
The club was where Sydney's legion SP bookies settled up with punters after Saturday racing. In its 1960s heyday there were an estimated 10,000 SP bookies stationed across the state's pubs and saloons, taking bets from as little as a threepence to hundreds of pounds.
"Off-course betting was very big back then," Pitts says. "They used to signal the odds from the paddock at Randwick to SP bookmakers in rooms overlooking the course."
The two level Corinthian room at the Sydney's City Tattersalls Club.
Settling typically finished around lunchtime on Mondays, when bookies adjourned to the upstairs snooker room or played cards (with a few bets on the side, of course). Some would keep drinking until 7pm at the Lower Bar, before heading to dinner and the iconic Chequers nightclub.
City Tatts also boasted the legendary personal trainer George Daldry, who ran its gymanisum for 20 years and trained everyone from Hollywood star James Mason to Monaco's Prince Albert, as well as countless cricketers, rowers and rugby players, including McCarthy and fellow Souths hero John Sattler. Later he managed Kerry Packer's gym and trained US President George H. W. Bush.
Daldry, who died at the end of 2011, was appointed to the Order of Australia in 1984 alongside media tycoon Rupert Murdoch, businessman Alan Bond and Olympic sprinter Betty Cuthbert.
The City Tattersalls Harriers runners on Castlereagh Street, led by gymnasium director George Daldry.
In 1957, the club's safety deposit boxes were supposedly robbed of as much as 100,000 pounds, in what was billed in the newspapers as Sydney's biggest ever theft.
But nothing was officially reported stolen. In the book, Waterhouse theorises that the bookies preferred to cop the losses than expose themselves to taxation. "One of the difficulties is that if I had money in the box, and I say I have lost £10,000, then the tax man comes along and says 'now you owe me'," he says.
It wasn't until 1963 that City Tattersalls "embraced the unthinkable" and allowed women to join as associates, and later as full members. In more recent decades the TAB and online gambling have replaced the underground punting of old, but the club moved with the times, opening Silks Bar in 1992 with its bistro, poker machines and more casual dress code.
The club has now finalised plans for a $200 million, 40-storey residential tower which chairman Patrick Campion says will "take our club to its next stage as a pillar of entertainment and hospitality in the Sydney city centre".
Start your day informed
Our Morning Edition newsletter is a curated guide to the most important and interesting stories, analysis and insights. Sign up to The Sydney Morning Herald’s newsletter here.