The best friend of axed radio shock jock Kyle Sandilands is set to reappear in court over an alleged incident with a property investor in Sydney‘s eastern suburbs.

Simon Main, 55, was charged with one count each of common assault and stalking/intimidation after he was arrested by NSW Police last December.

He was also hit with an apprehended violence order application over the alleged altercation with Double Bay property investor Martin Border two months earlier.

‘Officers from Eastern Suburbs Police Area Command were told a 59-year-old man was allegedly assaulted by an unknown man after an argument over parking,’ a police spokesperson said.

‘Following inquiries, on Tuesday,  December 2, 2025, a 55-year-old man was issued a court attendance notice for common assault and stalk/intimidate with intent to cause fear of physical harm.’

The alleged victim was not injured.

Main appeared in Downing Centre Local Court last month, where he pleaded not guilty to both charges, The Australian reported.

Court documents allege that Main intimidated Mr Border ‘with the intention of causing him to fear physical or mental harm’.

Simon Main (pictured right with best mate Kyle Sandilands) has been charged common assault and stalking/intimidation in relation to an alleged altercation with a property investor

Mr Border was reluctant to comment on the alleged incident when previously contacted by the publication.

‘I don’t want to get involved… I wasn’t involved really, I don’t want to say any more,’ he said.

The matter and AVO are listed for mention in Downing Centre Local Court on Tuesday.

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

The pair have been friends for more than a decade.

Both men also count Sydney nightclub identity John Ibrahim, who was also part of Sandilands’ wedding party, a close friend.

Sandilands’ multimillion-dollar Vaucluse mansion is listed on court documents as Main’s address.

The stepson of Australian entertainer Barry Crocker, Main has a colourful past.

Simon Main dated US actress Nicollette Sheridan for three years in the late 1990s

The former Scots College student was once a personal assistant to singer Liza Minnelli and dated Desperate Housewives star Nicollette Sheridan for three years in the late 1990s.

His relationship with the British-born US actress ended in 2000 after Main was jailed over his role in attempting to shift 333,000 ecstasy pills worth $10million, in what was described at the time as the world’s largest ecstasy haul.

He spent four years of an eight-year sentence behind bars in Trieste.

When he returned to Australia, he managed a Kings Cross escort agency and was once known for ferrying sex workers to clients in a $200,000 limousine dubbed the ‘Booty Bentley’.