Nightclub boss John Ibrahim's loyal lieutenant Margaret Staltaro appeared nervous.
Police pulled her over on Spit Road, Mosman, one Friday afternoon in March, and discovered her car registration was cancelled and her driver's licence was suspended.
John Ibrahim and his business partner Margaret Staltaro.
But, according to court documents, police thought something else was amiss.
"When speaking with the accused, she averted her eyes from police ... and her hands were clenching and unclenching irregularly," the document said.
Staltaro, Mr Ibrahim's powerful financial controller, took a drug test, which was positive for ice.
"She was asked if there were any drugs in the car and she replied there was maybe something in there that she had confiscated from her nephew.
"The accused became more visibly nervous, holding the sides of her neck."
Police found 0.1 grams of methylamphetamine in a plastic bag inside her handbag, and a glass ice pipe wedged between the driver's seat and the centre console.
She was taken to Dee Why police station for further testing, which confirmed the presence of the drug in her system.
The 44-year-old pleaded guilty to driving under the influence, and drug possession last month, and was due to be sentenced on Wednesday.
Her barrister, Julieanne Levick, told Manly Local Court that Staltaro could not attend because she is recovering from surgery in Thailand.
Ms Levick offered to show magistrate Chris Longley a photograph of Staltaro to prove she was suffering from complications and was not well enough to fly to Australia.
The police prosecutor said: "She does appear most unwell in that photograph."
Staltaro is variously described as Ibrahim's "work wife" and the "female Tongan Sam", a reference to the Ibrahim family's enforcer Semi "Tongan Sam" Ngata.
Her court case comes a fortnight after dramatic police raids at Sydney properties, including Ibrahim's Dover Heights mansion and Staltaro's nearby apartment over an alleged international drug syndicate.
Neither Mr Ibrahim nor Staltaro face charges in relation to the raids.
But Mr Ibrahim's brothers Michael and Fadi were arrested in Dubai, alongside Sydney underworld figures Steven Fawaz Elmir, Haykan Arif and Mustapha Dib.
Police arrested 10 people in Sydney, including Mr Ibrahim's girlfriend Sarah Budge, who was allegedly found with a loaded Glock pistol.
His son Daniel, his cousin Sleiman Tajjour and his friend and real estate agent Ryan Watsford, 37, of Rose Bay, were also charged in relation to drug importation and dealing with more than $1 million in proceeds of crime.
Staltaro's court case was adjourned for six weeks, while she enters into a drug treatment program, and is subjected to drug testing.