- 1 minute 43 secondsSend in your questions for a special mailbag episode
We're coming to the end of season seven of this humble podcast, and as a thank-you (or alternatively, as a punishment), we wanted to open the floor to you. So if there's a question you've always wanted to ask John Silvester about a case, a crime, a cop, a crook, or his career, now is your chance.
Send your question directly to us by emailing [email protected] and Sly will select a few for a special mailbag episode.
Thank you for your support, comments and criticisms this season, and as we say, "There's a touch of evil in all of us."
See omnystudio.com/listener for privacy information.
2 June 2026, 7:00 pm - 37 minutes 30 secondsIn a world of two-bit gangsters, Charlie Wootton was the last old-school crook
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.
26 May 2026, 7:00 pm - 22 minutes 1 secondMy brother, the Great Bookie robber
On April 21, 1976, six bandits raided the Victoria Club where Melbourne’s biggest bookies were settling their accounts with cash. No one knows the exact figure, but the take was supposed to be in the vicinity of $15 million.
Just after the armed robbery, and a few kilometres away at a pub in the suburb of Windsor, Greg Carroll was meeting his brother, Ian Revell Carroll.
Greg remembers the smirk on his brother’s face when news of the robbery broke while they tucked into lunch.
What he didn’t know was that his brother was one of the six bandits behind one of Australia’s most notorious, and successful, heists.
Today, Greg speaks to John Silvester about the genius of the stick-up and then, the curse of the Great Bookie Robbery.For more:
- Gregory M Carroll's book '11 Minutes'
- A tour of the Naked City: Melbourne's crime secrets revealed by John Silvester.
See omnystudio.com/listener for privacy information.
19 May 2026, 7:00 pm - 1 hour 22 minutesNaked City special: A conversation with John Silvester
A couple of months ago we held a night for subscribers to The Age and Sydney Morning Herald, a conversation with John Silvester, hosted by crime and justice reporter Erin Pearson.
We recorded the whole thing and so for today’s episode, we bring you this special episode with Sly.
In the conversation, Sly shared how he became a journalist and then all the highlights from his long career – from the gangland war in Melbourne and his dealings with Carl Williams, how a Christmas card from Mark "Chopper" Read sparked a long relationship, and what was so different about Erin Patterson, who was convicted - and since appealed - of the notorious mushroom murder case.
You too can have access to nights like this by becoming a subscriber.
Background reading, watching and listening:
- Sly’s latest column – ‘You’re gunna get it’: How police stared down a double-murderer and prevented further carnage
- A tour of the Naked City: Melbourne's crime secrets revealed by John Silvester
See omnystudio.com/listener for privacy information.
12 May 2026, 7:00 pm - 53 minutes 15 secondsDon’t play god, don’t mess with their mail – in prison with the worst of the worst
Brian Coghlan is laid back, an asset he was able to use in his workplace. As a prison officer, he quickly learnt that being seen as a good guy around bad people was the key to life behind bars.
For 26 years at Port Phillip Prison, he dealt with the worst society had to offer – sex offenders, serial killers and manipulative mass murderers who knew they were destined to die in jail.
He spent most of those years working in the top-level protection unit that housed the likes of Peter Dupas, Julian Knight, Raymond "Mr Stinky" Edmunds and the Bega schoolgirl killers.
Coghlan decided very early to deal with each inmate on the basis of how they behaved in jail, not what they did to get there.
In this episode, he talks to John Silvester about the tricks to surviving in jail, as an inmate and as a prison officer, and his unique insight into some of the country’s worst inmates.Background reading/viewing
- John Silvester's full story on Brian Coghlan – 'Dealing with Victoria's most notorious killers'.
- John Silvester's latest column – '$500 to firebomb: How crime gangs are outsourcing Melbourne’s Bar Wars.'
- Foreign Correspondent, ABC, 'The man from Tobasco: The story of Carlos Cabal Peniche.'
See omnystudio.com/listener for privacy information.
5 May 2026, 7:00 pm - 42 minutes 48 secondsThe champion boxer and the crime boss who wanted him dead
Barry Michael was a professional boxer who made his name in the ring as a smart and brave fighter with a kit of wicked body punches.
Alphonse John Gangitano, a mobster who preferred a king hit to a fair fight, was in the corner of the talented Lester Ellis when Michael took Ellis’ world title.
The trouble was, Gangitano wanted the title back.
In today’s episode of Naked City with John Silvester, Michael recounts what happened when Gangitano ambushed him in a Melbourne nightclub, and what happened when "Sly" took him on in the ring.Background reading
- John Silvester’s story on Barry Michael.
- All of John Silvester’s stories and columns.
See omnystudio.com/listener for privacy information.
28 April 2026, 7:00 pm - 43 minutes 5 secondsThe cop, the sovereign citizen and the arrest that ruined a life
Michael Aston loved being a cop, or more specifically, a road policing officer. He said it was the best job in the world, until it wasn't. Aston is no longer a cop, with his career and mental health disappearing into the quicksand of the legal system where no one is accountable.
It was 2020, and the start of the dark days of COVID, when Aston was policing then-premier Daniel Andrews' lockdown laws that prevented Victorians from travelling outside a five-kilometre radius.
On a road outside of Coldstream, north east of Melbourne, Aston tried to pull over a driver to check his work permit – and encountered a sovereign citizen.
This was years before the name Desmond 'Dezi' Freeman ripped into the public's consciousness for shooting three police officers, two fatally, in the Victorian High Country.
But back in 2020, Aston's run-in with a sovereign citizen changed his life.
Aston and his wife, Deanna, open up to John Silvester in today's special episode of Naked City.
Background reading
- John Silvester's full story on Michael Aston.
- All of Sly's columns, and stories.
See omnystudio.com/listener for privacy information.
21 April 2026, 7:00 pm - 42 minutes 12 secondsThe top cop who used his music career to find Tony Mokbel
Former deputy commissioner and counter-terrorism boss Ross Guenther had a unique life before policing, playing in big bands with music greats Jerry Lewis and Barry White.
He was no slouch in his policing career either, heading up the counter-terrorism squad for Victoria Police.
In this episode of Naked City, he talks to John Silvester about a foiled terrorism plot, and how his music career helped him hunt down Tony Mokbel after the drug boss’ infamous escape to Greece.And if you want to read all of Sly’s stories, click here.
See omnystudio.com/listener for privacy information.
14 April 2026, 7:00 pm - 26 minutes 55 secondsThey were violent young offenders. But something happened to these ‘lost boys’ of Port Phillip
Anne Hooker worked as a prison officer for 13 years for Corrections Victoria, and Port Phillip Prison for a further 23 years.
She also set up and ran a unit in jail called Penhyn, which housed young men aged 18 to 25.
The unit became so highly sought after within the prison system that there was a waiting list to enter it, and as Hooker explained to Naked City host John Silvester, the environment she created in there led to recidivism rates (the times an offender returns to prison) slashed.
Anne Hooker is one of a handful of experts who has the practical and academic experience to provide at least some of the answers to the country's – and particularly Victoria's – youth crime epidemic.See omnystudio.com/listener for privacy information.
7 April 2026, 7:00 pm - 18 secondsWe'll be back soon
See omnystudio.com/listener for privacy information.
31 March 2026, 6:00 pm - 57 minutes 16 secondsTrue detective, Part 2: Hunting a cannibal, and other tales of homicide
Sol Solomon has investigated some of the country's worst, most high-profile and just plain bizarre homicides.
In part two of his interview with Naked City's John Silvester, the former detective talks about some of the most difficult cases - such as investigating the murders of police officers Gary Silk and Rodney Miller. And the best, like hearing a killer confess to a cold case murder of a single mother during an elaborate undercover sting.
He also reveals the strangest case...investigating a real-life cannibal.See omnystudio.com/listener for privacy information.
24 March 2026, 6:00 pm - More Episodes? Get the App