Dean Hugh Te Kahu William Wickliffe is a man with a notorious past.

He's robbed, burgled, thieved.

He's brandished god knows how many weapons, made drugs, taken hostages.

He's the only man to have escaped from the country's toughest prison twice. He's killed.

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He's spent more time in prison than any other New Zealander, bar one.

But he's never been on the internet, wouldn't know how if he wanted to; he's planning to build a dream home overlooking the ocean at a family property, once he's cleared the gorse off its entire surface; one of his best mates is a former prison guard he met on the inside.

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There is a lot people don't know about Wickliffe, and the Weekend Herald journeyed to the Bay of Plenty to sit down with the recent parolee for an afternoon and chat about his life, love, loss - and his regrets.

Wickliffe has more convictions than he can remember - "probably 40 or 50, I have no idea", he says.

He's well spoken, meticulously groomed and he's serious, but somewhat soft.

It's hard to imagine the man with the salt and pepper quiff, colour co-ordinated outfit and well shined leather shoes committing any of the offences that make up his extensive criminal history.

Wickliffe spoke to the Weekend Herald about his life of crime, and hope for the future. Photo / Brett Phibbs
Wickliffe spoke to the Weekend Herald about his life of crime, and hope for the future. Photo / Brett Phibbs

He says a fractious and traumatic childhood led him down the dark path of crime and the destruction of himself and others.

It all started when his parents separated.

His father Bill Wickliffe was an alcoholic and his mother Phyllis "abandoned" her young son after the break-up.

"I was 7-years old when my mother abandoned me," Wickliffe said.

"I had to fend for myself from then."

He left home in the small Bay of Plenty town of Maketu at 15 and made his way to Rotorua where he stayed for a while in a hostel for Maori boys that aimed to resettle them into city life.

Soon after that Wickliffe ran into a cousin who'd just been released from borstal.

"And really, that was the start of the life that led me to problems with the police," he said.

"We'd both been abandoned by our parents, our mothers were sisters, our fathers were both alcoholics."

The first crime Wickliffe ever committed was alongside that cousin, who was a couple of years older.

They broke into a warehouse where Wickliffe had been working and pinched £350 - the equivalent of an average yearly wage at the time - and fled to Auckland.

The pair enjoyed the spoils of their crime, the freedom it gave them to have money for once, to be able to buy food and all of the other things young lads want in life.

After three months the cash was all spent, but by then Wickliffe was "hooked on the lifestyle".

When he was 15 Wickliffe learned his mother was also in Auckland and he tracked her down, found her living with her two daughters.

She agreed her teenage son could move in, as long as he adhered to her strict no alcohol policy.

Phyllis had seen enough of the harm booze could do with Wickliffe's father, and the rule was not negotiable.

He agreed, but the arrangement - and the rest of his life, really - came undone on his 16th birthday.

"I came home under the influence, I was tipsy but not drunk, an she told me to pack my bags in the morning and leave," Wickliffe recalled.

"I went to stay at a caravan park and that's when I started to get into real trouble".

Dean Wickliffe, one of New Zealand's most high-profile criminals and prison escapee talks about his life behind bars. He is the only person to have escaped Paremoremo maximum security prison twice and he was New Zealand's longest-serving prisoner. / Brett Phibbs

Sixteen-year-old Wickliffe burgled his way around the city and got into a few scuffles, the latter leading to his first stint in a boys' home.

He spent three months there, followed by months in a youth detention centre and borstal "in quick succession", but that punishments did little to quell his criminal offending.

"Borstal, that's pretty much where you learn everything you need to know about the lifestyle," he explained.

"The criminal lifestyle, as much as it was about the need to have material things, it was about having the financial ability to lead a life.

"You just got in deeper and deeper with it, you got the attitude of being a minor outlaw."

At 19, Wickliffe committed his first prison-worthy offence, got his first taste of what grown-up jail was like.

"I decided it was time to step up, and I robbed a bank, and I kidnapped three men at gunpoint," he said, matter-of-factly.

"While I was in the bank a passer-by saw what was going on and removed the keys from my getaway car, so when I came out with the hostages I had no car.

"I hijacked the first car that I came across and forced the three men into it, forced one of them to drive me away.

"That led to a big manhunt across the Mangere area. I got away but I eventually got tracked down and arrested."

He was sentenced to three years for robbery, three for threatening to kill and three for kidnapping - all to be served concurrently.

Wickliffe was taken from court up to Auckland Prison, known as Paremoremo due to its location north of the city, and locked up inside the maximum security wing.

Known as D Block, the wing housed the worst of New Zealand's offenders who were all locked down in individual cells for most of the day, allowed out for just an hour or two to exercise.

"That was the first of four prison terms I did in D Block," Wickliffe said.

"I did 28 years in total at Paremoremo, in solitary confinement conditions for most of that, locked up for 22 or 23 hours a day.

"That really hardened me, made me angry, bitter."

Wickliffe's time in maximum security is the main inspiration for his upcoming book A Life Behind Bars, which is due for release in December.

Self-published with the help of a retired prison guard Wickliffe met and befriended inside, the book chronicles his lifetime of offending and the experiences he had in prison.

It also details, at great length, his thoughts on New Zealand's penal system.

Wickliffe said he bore witness to far too many suicides, self-harm situations, brutal beatings and other inhumane and cruel treatment of inmates and the book is his bid to help the public understand what is really going on in Kiwi prisons.

Inside, Wickliffe became a champion for his fellow inmates, fighting relentlessly for better conditions and treatment, to bring to light the atrocities he claimed were happening within the perimeter fence - especially in D Block.

Wickliffe being released on parole after serving 30 years. At the time he was New Zealand's longest-serving prisoner. Photo / NZ Herald Archives
Wickliffe being released on parole after serving 30 years. At the time he was New Zealand's longest-serving prisoner. Photo / NZ Herald Archives

Wickliffe's longest and most serious lag started in 1972 after he killed Paul Miet during the robbery of a jewellery store in Wellington.

He was convicted of murder and sentenced to life in prison, meaning even though he has been released by the Parole Board, if he reoffends or breaches any conditions imposed on his freedom he can be recalled to serve the remainder of his time - the rest of his natural life.

Wickliffe has always been adamant Miet's death was a tragic accident, that as the pair struggled during the robbery his loaded Luger pistol went off and fatally wounded the man.

More than 12 years after he was jailed, the murder charge was downgraded after a retrial.

However, the judge ruled that the life sentence was to remain - based on the fact that Wickliffe had entered Miet's store with a loaded firearm.

To date, he is one of only three people to be handed down a life sentence for a conviction of manslaughter, the other two being David Haerewa and Tania Shailer who violently abused and killed 3-year-old Moko Rangitoheriri in Taupo in 2015.

Wickliffe is bitter about the sentence and discusses that at length in his book, describing it as an injustice.

But he concedes he deserved to be punished for what he did to Miet.

"I do feel a deep sense of guilt - an innocent man died," he said.

"I can't change that, all I can do is change my lifestyle now so that nothing like that can ever happen again."

 Dean Wickliffe under arrest at the Auckland Central Police Station in 1991. Photo / NZ Herald Archives
Dean Wickliffe under arrest at the Auckland Central Police Station in 1991. Photo / NZ Herald Archives

Wickliffe was first paroled in 1987 - it would be the first of five times he would be released by the board to later reoffend, and be recalled back to prison.

He was released again in 1995 and soon after, charged with murdering Bay of Plenty man Richard Bluett.

A jury found Wickliffe guilty, but in 1998 after a retrial he was acquitted and the murder conviction was quashed.

His recalls in 2008 and 2011 were the result of true love.

Wickliffe met Dionne Chapman after a release in the early 2000s.

For the first time, he had found love - and he was desperate to hold onto it.

Tragically, Chapman was diagnosed with terminal cancer.

Wickliffe became her full-time caregiver, taking her to appointments, spending every minute of his day trying to ease her suffering.

Then in 2008 - after his longest ever stretch out of prison - he was recalled again.

Dionne Chapman was Wickliffe's partner for nine years before she passed away from cancer. Photo / Supplied
Dionne Chapman was Wickliffe's partner for nine years before she passed away from cancer. Photo / Supplied

He'd been caught with cannabis, the powerful prescription-only pain relief drug ketamine, controlled drug butanediol, also known as Fantasy, which is said to create feelings of euphoria and tranquillity for users, and a loaded gun.

He said the drugs were for Chapman, that she was reluctant to take her prescribed morphine and she'd asked him to get alternative pain relief.

She offered to take the rap when the police raided their home, but Wickliffe wouldn't hear of it.

"When I first met her she was given three months to live, but she was one of the first to be treated with herceptin (a breast cancer treatment drug) and that gave us nine years together," he said, his voice cracking and his eyes softening.

"That relationship kept me out of prison for eight of those nine years - seven years longer than I'd ever been out of prison before in my life; when I met her I hadn't been out of prison for longer than 17 months since I was 16.

"I guess you can call it a love story between a woman dying of cancer and a man who had never loved or been loved."

Dean Wickliffe talks about the reasons why he was arrested for drunk driving. Wickliffe one of New Zealand's most high-profile criminals and prison escapee. . He is the only person to have escaped Paremoremo maximum security prison twice. He was New Zealand's longest-serving prisoner.

Just weeks after Wickliffe went back to jail, Chapman passed away.

"Out of all the things I have had to go through in my life, that was the most difficult to get over," he said.

"I wasn't there for her, for the last weeks of her life - I'd been there for nine years, through all the ups and downs."

Wickliffe is far from over Chapman, and tears up when speaking about her.

"Our relationship was something that gave my life some substance, for the first time in my life I was doing something positive, something with meaning.

"All the years behind bars made sense all of a sudden, it prepared me for those nine years with her ... but losing her ... I still feel it seven years later."

The next time he was allowed out in 2011, a still-heartbroken Wickliffe turned to crime again.

Six months after he was paroled, Wickliffe was found at a Maketu property helping to make methamphetamine.

He later explained in court he'd accepted an offer of $10,000 to help manufacture a batch of the drug.

He needed the money, he said, to create an urupa (burial site) to bury Chapman at a coastal property he had inherited from his father's family.

And his love for Chapman has a part to play in his most recent legal saga.

Last month Wickliffe was charged with drink driving after being stopped by police in Papamoa.

He had a breath alcohol level of 754 micrograms per litre.

The legal limit is 250 micrograms.

Further, a special condition of his parole was that Wickliffe was banned from consuming alcohol.

Yesterday Wickliffe was appeared in the Tauranga District Court and through his lawyer, he entered an intimated guilty plea to both charges.

He was remanded on bail until his next date, which will be before a judge.

He also faces another recall to prison and will appear before the Parole Board in November.

Corrections applied for a recall soon after his arrest, but their bid to have him locked up again was rejected.

Dean Wickliffe celebrates a Warriors win at the Albion Pub in Hobson Street, Auckland in 2002. Photo / File
Dean Wickliffe celebrates a Warriors win at the Albion Pub in Hobson Street, Auckland in 2002. Photo / File

Wickliffe told the Weekend Herald that he had no excuse for driving under the influence - but wanted people to understand why he'd been drinking.

He said he wanted to plead guilty as soon as possible, to accept full responsibility for his alleged offending.

He had been to visit Chapman's grave that day with friends, and they invited him for dinner.

Finding out that he'd turned 69 on September 16, they decided to make the dinner a celebration as well as a night of remembering his lost love.

After dinner they went to a bar.

A sober driver had been organised for Wickliffe to ensure he could get home.

When his mates called it a night at about 11.30pm, he called the driver. No answer.

No answer at 12 or 12.30am either.

The bar shut at 1am and the courtesy van couldn't take him to his place. He had no cash for a cab.

He made the call to drive the short distance back to the house where he'd had dinner.

Police stopped him less than 100m from the property.

"I know I shouldn't have been drinking, I know I shouldn't have driven," he said.

"They got me. I'm not denying that."

Dean Wickliffe, reflecting on freedom and his 41 years behind bars. Photo / Brett Phibbs
Dean Wickliffe, reflecting on freedom and his 41 years behind bars. Photo / Brett Phibbs

He's worried about being recalled, but is resigned to the fact there isn't much he can do - it's all up to the Parole Board.

"I just have to accept the consequences for breaking the rules," he said.

If he manages to steer clear of jail, he has a plan - and for the first time in his life it doesn't involved crime.

"I never want to go back, I know I will never go back to that lifestyle that I had before," he said.

Wickliffe said writing his book had made him reflect and re-evaluate his life - and there were many things he'd do over if he could.

"I've had to review my whole life, relive those events right from childhood ... you get to see flaws you thought you never had and I try to be as honest as I can about my shortcomings ... I feel like I have a pretty good insight into why my life unfolded the way it did.

"An alcoholic father, a mother who wasn't present - I left home naive and ill-prepared for life.

"I entered the penal system which did nothing to help me, all that punishment, all it did was make me harder and more dangerous than I ever was before.

"I have this reputation as a badass 'notorious' criminal," he laughed.

"The media have written all the headlines about me over the years, but the people who know me know that's not true, they know there's a different side to Dean Wickliffe, that I'm not and never have been - in totality - the man in the headlines.

"There are parts of my life that I can't deny and I accept that, I've broken a lot of social rules ..."

One thing he is proud of is that he's never broken his own rules when it comes to crime.

He refers to himself as an "old-school" crim and says he and his mates from back in the day all abide to the same "code of ethics".

The rules are simple - you don't hurt women or children; you don't hurt or rip off the elderly or vulnerable; sex crimes are a big no no.

But stealing from big businesses or hurting someone who's come after you or your family is acceptable.

"It's not a crime to rob a bank, but it is a crime to rob someone who has worked hard for their income," he reasons.

"That's a line that we don't cross."

Dean Wickliffe says a fractious and traumatic childhood led him down the dark path of crime and the destruction of himself and others. It all started when his parents separated. Photo / Supplied
Dean Wickliffe says a fractious and traumatic childhood led him down the dark path of crime and the destruction of himself and others. It all started when his parents separated. Photo / Supplied

Cathartic is a word Wickliffe would use to describe the writing process - the book helped him find closure, and focus for however many years he has left on this earth.

He hand wrote the original manuscript in prison, filing 900 pages with his cursive script before reading and rewriting it - twice.

When it was finally ready, he approached several publishers, but decided to fund the book's release himself because he was not willing to compromise on the content, or soften it in any way.

"There's a lot of feeling in there, it's my life, I've lived it," he said.

"Some parts of it almost bring me to tears."

Knowing where he came from, where and why he went wrong for the first time was a game changer for Wickliffe and he wants it laid out, raw and brutal, for people to read in full.

"Having relived my life in writing this book, and being able to see all the turning points that I didn't take and how carelessly I lived and how wastefully I loved my life .... If I'd known that at the beginning, there's no way I would've gone down that track.

"I can't change the past; I can only change who I am today and who I will be in the future."

So what does the future hold for Wickliffe?

Several websites claim he's battling prostate cancer and may not have long to live.

"That's bullshit," he scoffed.

"My health is good ... prostate cancer? I don't know where they got that.

"I've never been on the internet, I don't know how and I don't know if I want to.

"I don't really care what people say about me."

What is true is that Wickliffe finds being free difficult.

He loves it, but the world changes so much every time he goes inside and he struggles to keep up when he's released.

"It's something that's very hard to describe," he said.

"Prison is the worst place you can imagine, for me it wasn't so much the physical confinement, it was the loss of free will.

"When you get out, it's like being in a time machine and waking up a few decades later and you're on an alien planet - everyone looks like you, but they're not like you at all.

"When you've lived by certain rules for all of your life, it's very foreign out here - you don't get taught in prison how to find relationships, things like the responsibilities around driving after you've been drinking alcohol.

"You have to relearn it all, you can't learn any of that in a prison cell."

He splits his time between Maketu, a mate's place in Te Puke, Hamilton where his "agent" and book publishing partner is based and Tauranga.

He spends time at his mate's sister's place, a mate he met during one of his many lags and is still inside.

He has another friend, a taxi driver who works nights and sleeps til lunch time but is supporting him in his latest life rebuild.

Wickliffe would like to get a job but finds it hard because "once people Google you they don't want to know".

And he wants to find love again.

It's what Chapman would have wanted, and what would make him happy and settled.

"I'd like to do that, and I'm hoping to get the financial means to build a small self-contained unit on my land so that I can retire," he said.

"With or without someone in my life, I will settle down on that land."

b• If you want to read more about Wickliffe's life and crimes, his book A Life Behind Bars will be available in December.