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Before it was called the Olympic Hotel, the venue was known as the Adelaide Hotel. In 1936 it was rebuilt, renovated, and renamed — reflecting the era's taste for modern-sounding names and Art Deco architecture.

• NSW pubs of the era were heavily influenced by Tooth & Co. brewery ownership
• New licensing laws prompted widespread Art Deco rebuilds across Sydney
• The renaming to "Olympic" captured the optimism of the 1930s
• Pubs then served as accommodation houses, job-hunting hubs, and political meeting places
• Local workers from Randwick Racecourse, Moore Park, and nearby industries were regulars

Like every Sydney pub, the Olympic Hotel lived through the infamous six o'clock swill — a peculiar chapter of Australian social history that shaped the physical design of pubs for generations.

• NSW law forced pubs to close at 6 pm from 1916 to 1955
• Workers would flood the bar straight after knock-off, drinking as fast as possible
• Hundreds of beers were consumed in under an hour each evening
• Bars were built long and narrow specifically to serve standing crowds at speed
• Very little food or seating — just wet counters and packed bodies

The Olympic Hotel's location made it a natural gathering point for Sydney's sporting culture. Sitting close to three major venues, it became part of the pre- and post-match ritual for generations of fans.

• Steps from the Sydney Cricket Ground, Sydney Football Stadium, and Royal Randwick Racecourse
• Meeting point for punters trading race tips before Randwick meetings
• Post-match drinking spot for cricket fans and rugby supporters alike
• Saturday afternoons would see the pub packed with race-goers and footy crowds
• The pub was woven into the social fabric of Sydney sport

The Paddington of today — affluent, artsy, full of galleries and boutiques — is unrecognisable from the mid-century neighbourhood the Olympic Hotel served. The pub existed in a very different world.

• Paddington was considered run-down working-class housing, with terrace houses near slum conditions
• Patrons were dockworkers, tradesmen, and factory hands — not café visitors
• Local stories describe boxing matches in the street outside
• Police visits late at night were not uncommon
• Informal gambling reportedly took place in back rooms — unremarkable for Sydney pubs of the era

From the 1960s through the 1980s, Paddington transformed dramatically. Artists, architects, and young professionals discovered its Victorian terraces, and the character of the neighbourhood — and its pubs — shifted entirely.

• Terrace houses that were once near-slums became desirable inner-city homes
• The old crowd of labourers and factory workers gave way to artists and designers
• University students and young professionals reshaped Paddington's nightlife
• The pub adapted, as it always had, to whoever the neighbourhood became
• That layered history — rough and refined — is still part of what the Olympic Hotel is today