At the time he got a 14-year-old girl addicted to drugs, forcing her into sex work.
Three weeks after his release in 2003 for those crimes, Isherwood and a co-offender targeted an 18-year-old model.
The group were in a motel room when, according to reports at the time, she said she didn’t intend to have sex with the men.
She was instead “forcibly injected” with ritalin and methadone, drugs found in her blood after the attack, before being raped and forced to perform degrading sex acts with both men.
Isherwood was found to be the leader of the two and at his sentencing in 2004 responded to the sentencing judge’s comments that his offending was the highest end of the spectrum by saying: “Sweet”.
Isherwood was sentenced to preventive detention at the Christchurch High Court in 2004.
He had attempted to appeal his preventive detention, with partial success at the Court of Appeal in relation to his drug charges.
He was later denied leave to appeal the rest of his sentence by the Supreme Court in 2010.
Isherwood was released on parole in September 2020 but recalled to prison in 2021 when he was struggling with his personal life, turning to prescription drug abuse and the Mongrel Mob.
His most recent recall to prison gave rise to two new charges, including one of receiving property, but both were withdrawn.
He faced the Parole Board in April last year, and again in October.
At his October hearing it was heard he had completed a drug treatment plan for the second time and “had behaved well”, according to the board.
Previously affiliated with the Mongrel Mob, Isherwood had since left the gang and returned his patch with the support of Corrections officers.
His release into the community comes with a “very tight series of special conditions” that will be imposed for life, but will be reviewed at a monitoring hearing in August this year.
The long list of conditions included a daily curfew, electronic monitoring, a ban on drugs and alcohol as well as a ban on entering alcohol stores, and counselling - psychological and for addictions.
He will also have to disclose intimate relationships, obtain permission from his probation officer to change jobs, and to have no contact with children under 16.
The Parole Board said it had earlier concerns about allegations of violence, as well as his gang affiliations, but believed he was no longer an undue risk to the community.
