No one has been in the headlines more than restaurateur Molloy.
Marketing strategist and Portage Licensing Trust board member Ben Goodale tells the Front Page podcast he isn't surprised to see a candidate provoke controversy for attention.
"One of the biggest problems with this campaign is that many Aucklanders are left wondering: 'Who are these people?'" says Goodale.
"Leo is a personality and he courts publicity. He's almost adopting a Trumpian approach where he knows that by being outrageous, he'll get headlines and talk on social media. And the worst thing in politics is to not be talked about. It is fundamentally helping Leo because a lot of people didn't know who he was before the election unless they followed some of his other hostile remarks. But they certainly know who he is now. "
Given that the campaign still has a couple of months to run, Goodale says we can expect to see more "mischief" from the candidates as they grapple for attention with their relatively modest budgets.
Molloy is one of a number of candidates generally identified as leaning to the right – and splitting that share of the vote.
On the other side of the spectrum, we have frontrunner Collins who hasn't been able to command the type of following that saw Phil Goff secure 48 per cent of the vote in the last mayoral election.
"Collins isn't as well known as Goff, who came in as a cabinet minister and real heavyweight Labour figure. Collins is a counsellor from South Auckland and he still has a bit of a profile to build."
Collins has, however, secured the endorsement of both Labour and Greens, solidifying his position as the main candidate on the left.
Things are far more ambiguous on the right in that the National Party hasn't openly thrown its support behind any of the candidates running.
Viv Beck does have a thumbs up from National Party-aligned lobby group Communities and Residents, but the National Party continues to have a policy of not endorsing candidates at local government elections.
Goodale sees this as a missed opportunity that leads to confusion among voters and allows fringe candidates to over-index in local elections.
"If you look at this from a branding point of view, it's much easier for voters to go 'I'm voting the National or Labour candidate for mayor'. That's a far clearer choice than a long list of names we don't know terribly well. This leaves voters without the shorthand understanding of what candidates stand for."
Goodale adds that would-be politicians running independent can also be risky in that they aren't beholden to
"My slight worry about independent candidates running is that they're unfettered from any political party perhaps providing robust strategic support, platforms or a manifesto, which provides a safety net," says Goodale.
"For example, if you vote for the Greens or Labour, you are voting for certain principles. An independent, on the other hand, can fundamentally say whatever they like.. So it is a risk and we saw this with Trump in the US. Although he was standing for the Republicans, he could have just stood as Trump given that he was doing his own thing the whole time."
Add to this the worrying reality that only a small proportion of Aucklanders vote in local elections and we could end up with a little-known candidate given a mandate by a tiny proportion of eligible voters.
We'll have to wait until October to see where that might lead us.
• The Front Page is a daily news podcast from the New Zealand Herald, available to listen to every weekday from 5am.
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