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Sir Tim Shadbolt, the former Mayor of Invercargill, former Mayor of Waitemata City, former student radical, serial candidate, larrikin and risk-taker has died, aged 78.

At his best, he was a gregarious and charismatic leader with an almost perpetual smile on his face and a distinctive drawl.

But he was a magnet for trouble and his final years in office were marked by bitterness and infighting over his competence as Mayor of Invercargill. He was voted out of office in 2022. All up, he was Invercargill mayor for 27 years in two separate stints.

Sir Tim Shadbolt in April 2019 with Governor-General Dame Patsy Reddy after receiving his knighthood. Photo / Govt House

Shadbolt was knighted in the New Year’s Honours in 2019 as New Zealand longest serving mayor at the time and during his eighth and final term as Invercargill’s mayor.

He first served as Invercargill mayor from 1993 to 1995 but while he was mayor, he contested the parliamentary byelection in Selwyn, Canterbury, for New Zealand First. He then fought his 1995 campaign for re-election from Paris which he was visiting as part of an anti-nuclear testing protest trip.

Unsurprisingly, Invercargill dumped him at the 1995 election.

“I’ll never try to organise a mayoral election from Paris again as long as I live,” he wrote in the book “A Mayor of Two Cities” (Hodder Moa 2008).

He claimed that his motivation for standing in Selwyn was to win the seat vacated by Ruth Richardson and hold the balance of power to acquire a new hospital for Invercargill. But instead, “it was seen as a rampant act of opportunism, disloyalty and desertion – the locals were not impressed.”

His fortunes turned and in 1998, Shadbolt was re-elected as Invercargill mayor.

He met his long-term partner, Asha Dutt, not long after he first became Mayor of Invercargill and she has been especially supportive in his declining years. They have a son.

In 2006, his former wife, Miriam Cameron, detailed several serious episodes of violence at his hands in the 1970s and 80s including an assault that required medical treatment.

They had two sons, and Shadbolt had another son from a previous marriage.

In his book, he wrote that it may not look good but he considered himself to be a very lucky man all his life in terms of wives, fiancees and girlfriends.

“Admittedly things haven’t always worked out in the long term but I’ve enjoyed so much romance and adventure and have always been sheltered and looked after.”

Not long after becoming mayor, the then head of Southland Institute of Technology and later National MP Penny Simmonds proposed a zero fees scheme to help rejuvenate the city and to keep and attract people to the region.

Shadbolt promoted it and enrolments increased from 1000 to 4000, although some others believed it was “cheating.”

He was a champion for Invercargill and Southland and in 2008 he campaigned in Auckland to promote Southland as a place that offered a better lifestyle.

Tim Shadbolt walked around the Skywalk on the Auckland Sky Tower towing a Southland flag in 2008 as part of a campaign to woo Aucklanders to Southland for a better lifestyle. Photo / Martin Sykes.

Shadbolt served 24 consecutive years as Mayor of Invercargill. But his last two terms were dogged by a defamation suit taken out against him by a fellow councillor, Karen Arnold, and an investigation by the Department of Internal Affairs into conflicts at the council.

In an interview with the Herald on Sunday in 2020, he said one of the reasons he would be seeking re-election in 2022 was because he needed the money.

“I just can’t believe this has happened to me when I have ... transformed this city from a bit of a rural backwater to an exciting place with movies and events,” he said. “I’ve just been destroyed - a bit of a tragic ending for a comedian really.

“I owe lawyers bills of $350,000, and there is just no way I can pay it, so what I am staring down for my retirement is bankruptcy.”

A jury in 2018 found no defamation had occurred and Arnold was ordered to pay costs. However, Arnold could not pay and was eventually made bankrupt.

When Shadbolt first won in Invercargill, he had previously served two terms as Mayor of Waitemata from 1983 to 1989 when he lived in Auckland.

Shadbolt was born in Auckland in 1947. His great-grandfather, Benjamin, had been a convicted criminal and was sent to Australia and then Norfolk Island for 17 years of hard labour before arriving in New Zealand. Shadbolt’s father Donald (also known as Tim) was raised in West Auckland and attended Mt Albert Grammar. He trained as a pilot in the Second World War and fought for the British Navy in the Fleet Air Arm.

When he returned to New Zealand after the war he took up teaching near Whakatane but not for long. He answered the call to retrain in Britain for the Korean War but was killed during a training flight when Shadbolt was aged five and his brother Rod aged two.

Shadbolt’s mother, Josien (Poppy), was of Dutch heritage and had arrived in New Zealand aged 18. She had been raised in Indonesia and attended school in the Netherlands and after her husband was killed, took her sons to Holland. She decided to return to New Zealand, where Shadbolt attended Blockhouse Bay School and became a foundation pupil at Rutherford College.

Shadbolt said he first got back to New Zealand, he had to go to speech classes to be taught how to speak. And there he had learned oratory which had changed his life.

“Because I was taught to be a public speaker, I could stand up,” he wrote in “A Mayor of Two Cities.”

“I stood for election to become the milk monitor and won; then I stood for election to become the bus monitor and won that too. When I got to high school I stood for election to become a prefect and won, mainly because I could speak with confidence. I could present my case.”

Shadbolt’s mother remarried a refugee from Czechoslovakia, whom Shadbolt loathed - although he loved his half-brother, Peter - but he credited his step-father for teaching him to work hard.

Shadbolt spent a year in 1967 working on the Manapouri power project.

He then went to Sydney where he got a job as a plasterer’s labourer in a building gang. But it was to end in tragedy in 1968 when the concrete first floor of a shop they had been working on in Cronulla collapsed. Shadbolt bolted for the door and threw himself onto the road. Four other workmates who had been working on the ground floor were killed, including his boss, and seven others were injured.

Sir Tim Shadbolt said in 2020 it had been a bit of a tragic end for a comedian. Photo / Getty Images for NZ Herald.

Shadbolt helped the police to identify the victims and after informing the families at the hospital which men had died, he rang his mother and asked for an airfare home to New Zealand.

Shadbolt developed a national profile as a student radical in the 1960s and 70s and had been especially active in the movement against the Vietnam War.

He had been president of a group he called the Auckland University Society for the Active Prevention of Cruelty to Politically Apathetic Humans.

He had been active in the Progressive Youth Movement, a former editor of the Auckland University student newspaper, Craccum, and had been arrested 33 times, including twice for using the word “bullshit” in a speech.

Those arrests were referenced in “Bullshit and Jellybeans,” his first book, published in 1971 by Alister Taylor.

In the book, he details the first incident which took place outside Mt Albert Grammar School on Alberton Ave. He had been invited to speak by a senior student to the liberal studies class. The headmaster banned him when he found out, so the students asked Shadbolt to speak from the back of a truck over the school wall. He estimated about 200 boys and 10 teachers gathered to listen.

Afterwards, Shadbolt was arrested for indecent language in a public place, to which he pleaded guilty and told the court exactly what he had said: “The official reason for New Zealand’s involvement in the Vietnam War is based on a firm foundation of solid bullshit.”

Shadbolt was fined $50 which he refused to pay and so was sent to Mt Eden prison for 25 days.

There he made friends with the famous folk hero and burglar George Wilder who had escaped from prison five times, and Trevor Nash, a convicted robber who escaped from Mt Eden.

Shadbolt wrote that he had spent a lot of time with Wilder “who turned out to be a tremendous guy.”

“I never met a guy who was such an honest, natural disliker of authority.”

Shadbolt was charged again in 1971 for using “bullshit” at a “teach-in” at Albert Park in Auckland about prison conditions following a riot at Mt Eden prison the previous day.

Tim Shadbolt dancing the Foxtrot with Rebecca Nicholson on "Dancing With The Stars" at Avalon TV studios in 2005. Photo / Neil Mackenzie.

One of Shadbolt’s witnesses in the ensuing trial was a science student, Maurice Williamson, who went on to become a National Party cabinet minister. Williamson testified that he thought Albert Park was a free-speech area, and many others besides Shadbolt had used the same language.

In the book, Shadbolt was scathing about the news media, especially the New Zealand Herald, which he believed was biased against protestors.

He said that when he and Miriam had their first son, the Herald rejected the birth notice he had tried to get published. It had read: “Shadbolt to Tim and Miriam Oct 7. A young revolutionary son. 8 and a half lbs (allowing for exaggeration). National Womens. Our thanks to the Welfare State and those who man her. Both well.”

In 1970, Shadbolt set up a commune in Huia in the Waitakere ranges and set up a concreting contracting business as well. He lived in the commune for five years.

Soon after being elected Waitemata mayor, Shadbolt got the mayoral Daimler to tow his concrete mixer in the Henderson Christmas parade. He also lost the mayoral chains twice, once stolen from a bag in his car outside the Gluepot in Ponsonby where he had been performing with Gary McCormick and Bruno Lawrence, and the second time, permanently.

Shadbolt was re-elected to Waitemata in 1986 in a landslide and with a “Tim’s Team” ticket but his management skills were highly controversial.

In 1988 his deputy mayor, Gary Taylor who went on to form the Environmental Defence Society, resigned citing mismanagement by Shadbolt.

Shadbolt stood as mayor of the new Waitakere City in 1989 but lost to Assid Corban.

In the next few years that followed, he became a serial candidate, nearly always unsuccessful. He stood in the byelection for Auckland Mayor when Dame Cath Tizard resigned to become Governor-General.

He stood for the Auckland mayoralty again in 1992 at the same time as standing for the Dunedin mayoralty.

He stood for Parliament as an independent in 1990 and in the Wellington Central byelection in December 1992 to replace Fran Wilde who had resigned to become Wellington mayor. His election manifesto was titled “Absolutely Positively Full of Shit.”

He finally found success for one term in a byelection for the Invercargill mayoralty in 1993 following the death of Eve Poole.

After being voted out, he stood unsuccessfully for Parliament again in 1996 for the Aotearoa Legalise Cannabis Party in Christchurch East and became the party’s deputy leader before regaining Invercargill in 1998.

He gave lots of things a go, especially if they involved publicity.

He appeared as a celebrity guest on the quiz show The Weakest Link. He took part in “Dancing with the Stars”, he had a small part in the movie “The World’s Fastest Indian” based on the life of Invercargill motorcycling legend Burt Munro, he was a guest on the comedy show 7 Days, and went to Borneo for an episode of “Intrepid Journeys.”

He even helped to advertise cheese with the famous slogan “I don’t care where, as long as I’m mayor.”