In a world of two-bit gangsters, Charlie Wootton was the last old-school crook

In a world of two-bit gangsters, Charlie Wootton was the last old-school crook

From Naked City by The Age and Sydney Morning Herald

May 26, 2026 · 38 min · Season 7 · Episode 19

About this episode

The episode discusses the life and legacy of Charlie Wootton, a respected figure in Melbourne's illegal gaming scene, through the perspective of his son Robert Wootton.

One of the underworld's old guard passed away quietly this year. Charlie Wootton didn’t need to be well known to be well respected in shadows occupied by hard men, controlling Melbourne’s illegal gaming industry long before the glittering behemoth of Crown casino. Though he posted death notices paying tribute to notorious crooks killed in the gangland war, Wootton was determined to keep a low profile, never mentioning the names of the celebrities and politicians who would attend his illegal gaming dens. Today, his son Robert Wootton talks to John Silvester in an unusual episode of Naked City . Unusual because decades ago, those same gaming houses run by Charlie Wootton were the target of Sly’s father, a respected gaming detective by the name of Fred Silvester. Further reading/listening The singing detective , Naked City, season one. John Silvester's latest story – 'Greed and hubris: The inside story of a legal scandal.'  See omnystudio.com/listener for privacy information.

People in this episode

Host: John Silvester

Guest: Robert Wootton

Topics covered

  • Melbourne underworld
  • illegal gaming
  • gangsters
  • crime history
  • family legacy

Keywords

  • Charlie Wootton
  • Melbourne
  • illegal gaming
  • gangsters
  • John Silvester
  • Robert Wootton
  • Fred Silvester

Mentioned in this episode

Organizations: Crown casino, Naked City, The Age and Sydney Morning Herald

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