Mr Judd won the mayoral chains in 2013 in a landslide victory over the incumbent mayor Harry Duynhoven.
He was catapulted to national prominence in the past several days after announcing he would not seek re-election, as abuse had been heaped on him over his failed campaign for greater Maori representation and he did not want to become a catalyst for division.
He said his worldview had changed radically since confronting his own attitudes toward Maori, after his involvement in a return of leasehold properties that had been confiscated in the wake of the New Zealand land wars.
He said he had harboured entrenched racist views throughout his life, which he had first learnt as a child in Masterton.
"I had a beautiful upbringing, a blissful and great time through my childhood. My Dad ran the YMCA in town there, and one of my best mates was Aaron Slight.
"I spent summers at Riversdale beach at the YMCA camps, I was a choir boy and altar boy at St Matthew's. I went to Lansdowne Primary then through to Hiona.
"But it wasn't until I became the mayor here that I even went on to a marae. Did I have any Maori mates when I was a kid? Only in my class.
"I've gone back to find things out. I call myself a recovering racist, and I've gone back to find out how did that all start," Mr Judd said.
He recalled cycling to class at the then Makora College on the east side of the town, and riding past an area colloquially known as "the Cameron Block or the reservation", where a relatively greater number of Maori families were living.
"One of the things I was told was to 'mind your lunch because you've got to pushbike past Cameron Block to school'.
"So I would get to that stretch of road and I'd get over the bridge and I'd bike as fast as I could until I got past the Cameron Block homes, the Maori homes. But nothing ever happened. Never.
"That's how it was back then, that's how I was," he said.
"Now that I've come to snap out of it, I realise I had a privileged white upbringing, absolutely. Not dollar privilege but ethnic privilege for sure."
"All of my life it's been ingrained to think a certain way and not just by my immediate family but the environment I grew up in, and New Zealand, actually.
"Another thing I remember was driving through Cameron Block as a kid and I said, 'aw look there's a house with sheets for curtains'. I was told not to stare, it was rude, and that they were just Maoris.
"We talk in code as Europeans, you know, all that ugly stuff. I had to confront that within myself and it's so deep-seated, it can come back up at times.
"Culturally, we have differences. Of course there is one law and one rule, no one's arguing that, but as far as world perspectives, culturally, we are different, and that's something to celebrate I've come to realise.
"A central government politician, and I will not name them, said the losers must follow the law of the victor, and I've heard our democracy described as two foxes and a hare deciding what to have for dinner, and that you must be more fox-like."
Mr Judd said he had believed in a "sanitised version of our colonial past", which he had now renounced, and he urged Masterton councillors to continue to "have this conversation" about Treaty-based representatives on council.
"Only the decision of a council to have a Maori ward can go down the road of having a petition and a poll. Other wards don't. That's racist," he said.
"But people will say that a Maori ward is race-based. It's not, it's Treaty-based," he said.
"It's only race-based when a council decides to do it. It's dog-whistle politics."
Mr Judd said he was considering writing a book about his life as a "recovering racist", and wanted to work to help others shift what might be their fundamentally jaundiced understanding.
"I get emotional about this. it winds me up. Look, we are good people, we're just blind to this part of us which has such a deep and lasting effect," he said.
"This is a question about who we are. It transcends local government and mayors. This is a fundamental question for us all. Ask yourself.
"I feel the safest, and the most connected and relaxed, in a Maori environment now. I almost feel at home on a marae now.
"Not only because of the changes within me but the whole way in which Maori connect with each other. It's that sense I would lead my children to, and that sense I've discovered, and that middle New Zealand is missing out on.
"What I'd like to do after this is help Pakeha transition to the road and the journey that I'm on. Not everyone will connect and that's fine, but I'd like to work in that space now."
