Brian Andrew Kaiser, 46, was on parole for killing his estranged lover when he followed his new on-again-off-again partner to Redhead beach, choked her until she lost consciousness and forced her head into the sand.

Kaiser was jailed for nearly 11 years for orchestrating the killing of Shandele Macey at Rutherford in 2006.

Last week he was jailed for a maximum of five years for choking and stalking the woman at the beach in 2017.

But it is the combination of those two violent acts targeting defenseless women, against the background of an 18-year criminal history littered with assaults, intimidation, apprehended violence orders and years spent in jail, that has led the state of NSW to apply for Kaiser to be declared a “high risk offender”, a man so likely to commit another serious offence that he should be subject to a strict three-year Extended Supervision Order (ESO).

The making of an ESO essentially comes down to a risk assessment.

What chances are there that this person, who has committed one or more heinous acts, will commit another? And the orders are often an intense invasion of privacy; they allow Corrective Services NSW to electronically monitor, counsel and visit the offender around the clock.

In a preliminary judgement published this week, NSW Supreme Court Justice Michael Walton outlined the state’s case for making such an order against Kaiser.

There was, of course, the manslaughter offence in 2006. When Kaiser organised for Jeremy Hunt to “sort out” Ms Macey over what Supreme Court Justice Graham Barr said were "imagined slights" and a $300 drug debt.

There was the escape from jail at the South Coast Correctional Centre in January 2016 where he rammed a stolen car into a petrol bowser in a bid to “blow himself up”.

Kaiser was classed as a minimum security prisoner in Nowra at the time, allowing him to perform maintenance work outside the jail’s main walls, but still on its grounds.

He was not always directly supervised while working but was required to report to a Corrective Services officer at regular intervals, police said.

It was during one of those work assignments that Kaiser fled the jail, making his way to Old Southern Road, stealing a black Mercedes Eco van.

​The owner of the van chased after Kaiser in another vehicle while on the phone to police, allowing officers to catch up with Kaiser on the Princes Highway.

He refused directions to stop, continuing to drive until he reached a roundabout on Central Avenue, next to the Coles Express Shell service station.

Police ​who witnessed what happened next said Kaiser’s vehicle went through the roundabout, jumped the gutter and accelerated towards a petrol bowser, crashing into it at about 50km/h.

He pleaded guilty to a number of charges and was sentenced to an additional two years’ jail

Then, five months after he released from jail, there was the stalking and choking of the woman at Redhead beach.

“A feature of the offending is an obsessive or controlling behaviour towards female victims,” Justice Walton said.

“The violence typically stemmed from a misperception of the relationship, his disquiet as to the victims’ reaction to him or the declining status of the relationship.”

Justice Walton said he was satisfied the state’s material justified the making of an ESO, but asked for Kaiser to first be assessed by a psychiatrist and psychologist.

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