The Former Seven Network presenter has been subject to "bullying and taunts" from prison officers because of his previous profile and had spent weeks in isolation from other inmates, his barrister Arjun Chhabra told the NSW Supreme Court on Tuesday.
Mr Chhabra referred to the "inhumanity of his condition while incarcerated", saying O'Keefe suffered from spinal and nerve pain he wasn't being treated for, had reduced vision due to an altercation with corrective officers and had not been given all his medicines correctly.
O'Keefe now appeared to be surrounded by organised crime members and unwittingly privy to conversations between two competing outlaw motorcycle gangs and their criminal associations, Mr Chhabra told the court.
O'Keefe, who appeared by AVL, was charged in January with two counts of intentionally choking a person, three of common assault, and assault occasioning actual bodily harm.
Police say O'Keefe grabbed the 38-year-old woman by her throat, pushed her to the ground, and punched and kicked her in his Sydney CBD unit.
The 50-year-old claims he acted in self-defence.
At the time he was charged O'Keefe was already on bail for a separate alleged incident of assault after being arrested in September.
Mr Chhabra said the Crown's case in relation to the allegations of offences in January was "not strong" meaning there was a real chance of O'Keefe's acquittal.
Imprisonment was unlikely if O'Keefe was convicted over the earlier charges, but "not inevitable" for the recent alleged offences.
The Crown argued O'Keefe had a lot of personal problems, was really unreliable and had an ongoing ice addiction that was relevant to his offending.
In refusing bail Justice Robertson Wright said it appeared O'Keefe had a long-standing, significant drug problem that included using cocaine, meth and cannabis.
He acknowledged O'Keefe had virtually no criminal history and no significant history of violence, but said the offences were serious.
In response to Mr Chhabra's proposal that O'Keefe be released to spend three weeks in rehabilitation, Justice Wright said the drug use was unlikely to be addressed by a short time in a facility.
"Largely because of the inadequacy of the rehabilitation program proposed ... I am not satisfied that the applicant has shown cause why his detention is not justified and in those circumstances I have no option but to refuse bail," he added.
O'Keefe, a former lawyer and son of former NSW Supreme Court judge Barry O'Keefe, was a founding member of domestic violence charity, the White Ribbon Foundation, where he served as chairman in 2017.
The organisation - which went into liquidation in 2019 - said in a statement it was disappointed to hear of the allegations against O'Keefe, as with "many other distressing incidents of violence against women already this new year".
The organisation had already distanced itself from the one-time ambassador last year, and said it was "dismayed to hear the news" of his arrest.
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