The first time he was arrested, in the late 1970s, was for sailing to Bali with accomplices to buy $1.5 million worth of heroin. When returning to New Zealand waters, the yacht got into trouble at Karamea and was assisted by police who took Curtis and his crew back to the station for warmth and refreshments.
It wasn't until his arrest months later his rescuers learned a plastic bag they saw Curtis carrying at the time had been full of the illicit drug.
University of Canterbury criminologist Greg Newbold said Curtis was a "grand old gentleman" who was the "paragon" of criminals.
"He's the idealised type of criminal, the very likeable villain. There's two types of criminals, the gentleman and the flea, and he's the gentleman," he said.
"He was a hard man and lived strictly by the criminal code - the code of silence, the code of respectability, of being uncompromising in his interests. He was honest, dignified, staunch; a real gentleman."
An escape attempt during his first trial saw him become the country's first remand prisoner to be held in maximum security and the life sentence he received for the drug crimes was also believed to be a first, said Mr Newbold.
An appeal reduced that to 16 years, but he was soon sentenced again for conspiring to import heroin and cannabis from Fiji.
It was while serving his third sentence - for conspiring to import $1.5 million worth of LSD from Europe in 1990 - that he pulled off his most daring feat.
In 1993, Curtis and convicted murderer Michael Jeffrey Bullock cut through bars in Paremoremo's A block, and scaled a wall with a ladder fashioned from prison shelving and tape.
Mr Newbold said the escape added to his "prestige and mystique".
"He had the ability to get out of the country unseen and live incognito in the Philippines for many years and that adds to his position in the history of New Zealand criminals."
It was the tenacity of now deputy police commissioner Mike Bush that tracked Curtis to the Philippines, where he had been living with a fake identity, new partner, and a daughter.
He was caught out by technology when his fingerprints - taken after he tried to cash a forged cheque - matched those supplied by Mr Bush to Interpol databases.
Mr Bush declined to comment to the Herald last night, but in previous interviews police had described Curtis as "personable" and "easy to talk to".
A funeral for Curtis will be held at Grange Manor, 400 Dominion Rd, Mt Eden, Auckland, at 3pm today.