Now deputy mayor, he says "nothing has changed".
With a decade of city council experience under his belt, Mr Chesterman still believes central city car parking should be free to assist a struggling business centre.
He recognises that car parking is a revenue driver and providing free parks would have a financial and staff loss implication.
"But we need more than free parking to bring our CBD back to life," he says.
Mr Chesterman says several factors are required for a vibrant city centre.
"Hamilton needs unique shops offering unique products - not just a selection of national and international brand stores anyone can find in any mall throughout New Zealand and Australia.
"Another ingredient would be more central city residents. To attract those we need suitable accommodation, well-appointed with garages."
But opinions differ on saving the city heart.
Recently Waikato University Professor of Environmental Planning Bob Evans said there are three things Hamilton should do to ensure survival of its city centre.
Speaking at the third of the University of Waikato's Winter Lectures he said all new development outside Hamilton's built-up area should be stopped, all new and planned road construction should be halted, and car use and parking should be constrained in favour of bus lanes, bike and walk-ways; "discriminating" in favour of inner city developments.
"If we lose the city centre, Hamilton is finished."