Former Richmond player Jake King allegedly threatened to shoot and break the legs of a man and his family if he did not cough up $150,000, court documents reveal.
The ex-AFL hard man faced Melbourne Magistrates Court on Wednesday accused of attempting to extort money from Tony Mokdissi at Melbourne's Southbank on May 25.
The alleged victim is understood to be a business partner of former Richmond and Hawthorn forward Tyrone Vickery.
Vickery, who announced his retirement from AFL football on Wednesday, owns Hawthorn East restaurant Fat Monkey.
Prosecutors have outlined their allegations against King.
The 33-year-old is accused of "threatening to shoot and break the legs of the victim and his family" if he did not pay him $150,000 within four weeks.
Nicknamed "The Push-up King", he is also accused of harassing Mr Mokdissi throughout June using a communication device.
King faces six charges in total, including extortion, making threats to kill and threatening to inflict serious injury.
"These are some genuinely serious matters," Magistrate Franz Holzer said.
But the ex-Tigers dynamo appears set to fight the charges, and the case was adjourned to a contested hearing in January.
King's barrister Geoffrey Steward said there had been "fruitful" discussions with prosecutors and was hopeful of further progress.
"Let's hope that something tangible will arise as a result of the contested mention," Mr Steward said.
King, who played 107 games for Richmond, is due back in court on January 30.