Now, two and a half years on from that night he says he feels confident about where the city is and what he has delivered during his first term.
No more cars on the Golden Mile
If Lester is elected, he will remove private vehicles from Lambton Quay, Willis St and Courtenay Place to make the CBD more people-focused.
"We aim to transform the way people travel around our city and particularly in the Eastern and Southern suburbs, we'll upgrade our laneways, remove private vehicles from the Golden Mile, have more parking for electric vehicles, motorbikes, scooters and bikes and prioritise people when designing our city's spaces".
Lester would not confirm whether the move was a part of the Let's Get Wellington Moving transport package, saying instead it was something he was working towards and would deliver.
He did confirm a decision on LGWM would be announced by the end of the month, pending sign-off from Cabinet.
A decision was meant to be announced last August.
Ending Homelessness
In 2016 Lester campaigned on working towards New Zealand's first wet house to reduce homelessness.
That pledge has morphed into something called "supported living units" which will feature in the Arlington development at Mt Cook, subject to public consultation on the proposed partnership with Housing New Zealand.
This year Lester is doubling down on the issue of homelessness and wants to eradicate it completely.
"With our partners we're going to provide enough supported living units to get every single homeless person the care they need and the wrap around support services they deserve so there's no good reason for a single individual to live on our city's streets."
Welcome Home package
The Christchurch terror attack on March 15 has prompted Lester to emphasise the importance of building inclusive, diverse and strong communities.
His Welcome Home package contains several initiatives designed to integrate refugees and their families when they settle in Wellington.
They include free access to council facilities including swimming pools, library services and visitor attractions like Zealandia and the Zoo.
"This is one thing that helps get them out and about. If you don't have any income, it's hard to actually be involved in the city you live in."
