It may come as a surprise that this enthusiastic educator left school at 15. He went to Australia and, for about six months as a teenager, worked in a travelling circus before getting into the mines in Tasmania. Then it was prawn trawlers and coastal traders off Cairns. At 21 he was the youngest skipper of a trader in Queensland and, when he'd had enough of that, spent three years as a tourism boat captain.
He came back to NZ to work ferries going to the Chathams and, in 1996, returned to Wanganui.
It was then he had a work accident involving a rope - "it's no use crying over spilled milk, or a lost leg," he says with a smile - and now has a prosthesis. That didn't stop him captaining the PS Waimarie for a time, or from carving with his late father-in-law George Waretini.
"For ages people said to me, 'why don't you become a teacher?', because I always have a lot of time for young people.
"I think I was brought on board not only to help teach, but to give some worldly knowledge to the students, a Wanganui boy out in the world doing it."
Chester gives a lot of credit to principal Peter Kaua who saw potential in the cheerful bloke who wanted to help out. He admires the environment Peter has fostered at the school since he took over five years ago.
"Peter Kaua is focused on making the school safe for our children. We like to let them know they can come to school and be safe, that they won't be bullied, and also for them to have pride about feeling part of the school family.
"It doesn't matter if they're Maori or Pakeha, they're all my kids. They're absolutely wonderful kids."
Chester says he's really lucky to work with a great team of teachers and that everyone from the ladies in the office to the caretaker wants the best for their kids.
Principal Peter Kaua says Chester's employment is mostly funded by Work and Income, and that when talk started that the man dubbed Matua may have to leave because his funding was ending the kids weren't happy.
"They said to me 'sir, you've got to keep him on, we don't want him to go'.
"I'm going to get that funding one way or another, whether I have to apply for this or that."
That student achievement is something Chester takes particular pride in.
"I don't know if the students realise we get such pride in their achievements and seeing the adults they become."