Invercargill Mayor Tim Shadbolt is facing two familiar challengers for the city's top job.
One is a sitting councillor who is suing him for defamation, while the other is a man he once chatted to for more than a day.
In the often mundane world of local body politics, Mr Shadbolt is a charismatic character who's flourished in his adopted southern city.
"Invercargill really needed some good lively promotion to show we were kicking and active and creative, and into movies and all sorts of exciting things like that," says Mr Shadbolt.
He's served seven terms as Mayor of Invercargill and insists he's still enjoying the job.
"I love it. I just think it's so challenging. Every day is different," he says.
The 69-year-old always has a good story to tell.
He managed to fill 26 hours with broadcaster Tom Conroy in 2012, breaking the Guinness World Record for the longest television interview.
But now Shadbolt's chatty friend wants to call time on his mayoral career.
"I think he can look back on an era with great pride. But things have changed, the economics have changed, and that's why my skillset is specific for now," says Mr Conroy.
Conroy believes he has the drive and business background to tackle the city's big issues.
Another rival followed Shadbolt's career as a reporter for the local paper.
Karen Arnold's now a first term councillor who is suing Fairfax and Mayor Shadbolt for defamation, but still believes he's been good for Invercargill.
"He's been a great advocate and he's been very loyal to the city," says Ms Arnold.
"But I do think it's time that we had a future-focused Mayor, one that's looking ahead and not always just thinking about the things that have happened in the past."
She's calling for a culture change, starting at the top.
But it may prove tough unseating the country's longest serving mayor, who has a culture all his own.