For Mr Young, who's been homeless for 13 years, sign-waving isn't just a way of passing the time. "I got the message from passers-by that 'you're a bum, get a job'. So I said to myself, 'blow it, I'm going to concentrate and say a few things'."
And say a few things he does. The two-time mayoral candidate uses his signs to address topics in the headlines, a common target being Auckland's leadership.
"Whether we wanted it or not, the Super City was wham, bam, crash."
But Mr Young is reluctant to blame any particular group for his homelessness, instead focusing on his concern for others in similar circumstances.
"I've learned a lot about being homeless, how to fossick in jumbo bins for extra food, how to supplement your income, do odd jobs and try to pay for things like warrants of fitness. I never would have believed the struggle there is in being poor and oppressed."
Mr Young, who now survives on a sickness benefit, has lost contact with much of his family for pursuing what he admits may be an impossible cause. But despite his situation, he still gains satisfaction from the positive reaction of passing drivers - and he knows them all.
"That's unusual, he's a new punter!" he says as a grey car toots.