Underworld and building industry identity George Alex supposedly suffers from depression, anxiety, high blood pressure and a leg injury from a recent car crash that is so severe it may require amputation.
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But the health complications facing Mr Alex allegedly did not prevent him from threatening to kill a woman in a series of ''erratic'' and ''aggressive'' text messages and emails sent over the past six months.
On Friday, Mr Alex appeared in a Sydney court, facing three charges of using a carriage service to make threats to kill and to cause serious harm. The charges allegedly relate to a business dispute.
He was preparing for his coming appearance at the royal commission into union corruption when police arrested him on Thursday.
His appearance in court completes a horrid week for Mr Alex who, on Monday, was accused in the royal commission of running a business involved in paying kickbacks to CFMEU officials, engaging in standover tactics and employing notorious Sydney terrorist Khaled Sharrouf.
The allegations about Mr Alex's building industry operations have also caused divisions in the NSW branch of the CFMEU, with senior union officials expressing disquiet in recent internal meetings about the way some of their colleagues have allegedly supported Mr Alex over the past three years.
The court heard Mr Alex allegedly threatened to set his ''crew'' and his ''men'' on the woman's family if she did not repay him money he claimed he was owed.
After trying to locate him for a week, counter-terrorism police arrested Mr Alex in a hotel room at the Fraser Suites on Kent Street on Thursday. The 43-year-old father of four, who has no fixed address and lives from hotel room to hotel room, appeared calm in the dock and waved to his family.
Several text messages and emails were allegedly sent by Mr Alex to Anna Lee, between April and September, containing threats to kill her and her family members Emmy Lee, Sangki Lee and Jonathon Lee.
''[There were] threats to harm and kill the alleged victim and her mother, her father and her brother and threats to get his crew and his men involved in this,'' police prosecutor David Anderson told Central Local Court on Friday.
Mr Alex's business dealings and associations with high-profile criminals including ex-Comanchero bikie Bill Fatrouni were at the centre of explosive allegations before the royal commission into union corruption on Monday.
Parklea inmate and former business partner of Mr Alex, Jim Kendrovski, refused to provide evidence to the commission, saying he feared for the safety of his wife and three children.
Union official Jose Barrios said he received a threatening phone call from Mr Alex late last month after Mr Barrios questioned CFMEU NSW secretary Brian Parker about why the union was negotiating a workplace agreement with one of Mr Alex's businesses.
Fairfax Media has previously revealed how Mr Alex cultivated figures in the CFMEU and big building companies who supported his labour hire and scaffolding operations.
Mr Alex was granted bail under strict conditions, including that he be checked into a psychiatric ward in the eastern suburbs for at least five days.
