It failed when he could not secure a key parcel. He had to sell off four buildings "way under market value," he said, but added: "Had I not gone through that, I would not be where I am today."
His condominium project also ran into trouble. He had secured the promise of a bank loan to complete it, then the recession hit. Citibank pulled out in January 2009, and then Kuchma's partner died suddenly.
"I was devastated," he said.
The recession also halted a $1-billion waterfront development by another private investor. But Kuchma, with the help of city officials and the National Development Council, was able to borrow $13 million at a favorable rate and completed the condominiums in 2010.
The question is whether the work of Kuchma and other developers marks the beginning of a turnaround, or just isolated efforts.
Kuchma said another developer was seeking approval for a project on the northern end of downtown. Kuchma points out the new courthouse complex, a former department store that now houses artists' lofts and another historic building he owns and plans to renovate.
Back at his office, Kuchma has a giant aerial photograph of Manhattan's Flatiron building. He adjusts his glasses and points out several buildings and a triangular park near the iconic 1902 skyscraper.
"The mix of a city like Manhattan is much different from what people imagine," Kuchma said. "I think we can achieve that mix here. You'll see, in 15 years the population will grow and it will be a much more walkable, livable city with corner stores.... If Manhattan can work, why can't we do it in a tiny city like Bridgeport?"