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• Accused in connection with a reported dispute about parking
• Simon Main served as the best man at Kyle Sandilands’ wedding.

The closest friend of the dismissed radio shock jockKyle Sandilandsis scheduled to return to court regarding a claimed event involving a property developer inSydney‘s eastern suburbs.

Simon Main, 55, faced one charge each of common assault and stalking/intimidation following his arrest byNSW Police last December.

He also faced a violence order application due to the alleged conflict with property investor Martin Border from Double Bay, which occurred two months prior.

A 59-year-old man was reportedly attacked by an unidentified individual following a dispute about parking, according to a police representative.

After receiving reports, on Tuesday, December 2, 2025, a 55-year-old man received a court summons related to common assault and stalking/intimidation with the intent to instill fear of physical harm.

The claimed victim sustained no harm.

Main appeared at the Downing Centre Local Court last month, where he entered a not guilty plea to both charges,The Australian reported.

Court records state that Main threatened Mr. Border “with the aim of making him afraid of physical or psychological harm.”

Mr. Border was hesitant to address the reported event when contacted by the magazine earlier.

“I don’t want to get involved… I wasn’t really involved, I don’t want to say anything else,” he stated.

The issue and AVO are noted for discussion in the Downing Centre Local Court on Tuesday.

Main served as Sandilands’ best man at his April 2023 wedding to Tegan Kynaston.

The two have been companions for over ten years.

Both men also include Sydney nightclub figure John Ibrahim, who was also present at Sandilands’ wedding, as a close friend.

Sandilands’ multi-million-pound home in Vaucluse is noted in court papers as Main’s address.

The son-in-law of Australian performer Barry Crocker, Main has a vibrant history.

A former student of the Scots College previously worked as a personal assistant to singer Liza Minnelli and was in a relationship with actress Nicollette Sheridan, known for her role in Desperate Housewives, for three years during the late 1990s.

His partnership with the British-born American actress concluded in 2000 when Main was imprisoned due to his involvement in trying to move 333,000 ecstasy tablets valued at $10 million, which was then referred to as the largest ecstasy seizure globally.

He served four years of an eight-year prison term in Trieste.

After coming back to Australia, he oversaw an escort service in Kings Cross and was famously recognized for transporting sex workers to clients using a $200,000 limousine called the ‘Booty Bentley’.

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