Masters, once a physically impressive competitive kickboxer and aspiring rapper, rose to notoriety along with the street gang he founded in ÅŒtara in the early 2000s.
By 2008, Masters had started a music label, Colourway Records, and the Killer Beez were one of the fastest growing gangs in New Zealand.
The gang, with its bright yellow "colours", was also linked to a number of high-profile, unprovoked assaults.
In an infamous interview with John Campbell, Masters denied any connection between the Killer Beez and the violence, or any rumoured dealing of methamphetamine.
"We're against it, we hate it," said Masters, when asked of the gang's attitude towards P.
"I've got nothing to hide."
At the time of the interview, a covert police investigation called Operation Leo was already underway.
Less than three months later, police arrested Masters and 43 other Killer Beez and Tribesmen associates.
Police seized about $500,000 worth of P and cannabis, $20,000 cash, a large amount of stolen property, and motorcycles and cars under the Proceeds of Crime Act.
At the time of the arrests, Detective Inspector John Tims - now a deputy commissioner - said the Killer Beez tried to portray themselves as "modern-day Robin Hoods"
"They have attempted to achieve status through music and videos in connection with the youth of our community," said Tims.
"Based on the evidence secured throughout this operation and today, in simple terms they are drug dealers who are causing destruction and chaos in our community by their actions."
Masters, 30 at the time, was declined bail and spent four years in custody before finally pleading guilty to supplying methamphetamine, conspiracy to supply the Class-A drug, and laundering money through Colourway Records.
In 2012, Justice Kit Toogood rejected Masters' explanation that he simply introduced people to one another, rather than be an integral part of the supply chain, as a "complete fabrication".
Masters showed promise as a businessman and a leader, said Justice Toogood, but had used his skills to sell drugs.
"No doubt you used your mana to run the operation and you had a hands-on role."
He was sentenced to 10 years and five months in prison.
While the influence of the Killer Beez in the community was greatly diminished by Operation Leo, the Killer Beez continued to wreck havoc inside prisons.
One of the worst attacks was the fatal assault on prison guard Jason Palmer in 2010 in Spring Hill Prison.
Latu Kepu punched Palmer, who fell backwards and hit his head on the concrete. The Killer Bee was later convicted of manslaughter.
Members of the Killer Beez were also involved in the riot at the same Waikato prison in 2013, as well as attacks on prison guards at Auckland Prison in Paremoremo in 2016.