(Editor’s Note - The Observer began this documentary project in January 2011 with a coffee and a bull session with Neil O’Leary. We asked if he were willing to let us occasionally peek behind the curtain of his mayoral campaign, to sit in on strategy meetings, and to ride along with him on election day. The only ground rule was that sensitive information could not be published until after the election. Observer publisher John Murray first met O’Leary on election day 1995 when O’Leary was the driver for seven-term mayor, Mike Bergin, and Murray was shadowing Bergin for the day. Bergin lost that election to Phil Giordano, and at a post-election party, at the Hills Restaurant, O’Leary told Murray that the Democrat Party was now in the hands of Mike Jarjura. Six years later Jarjura was elected mayor and served for ten years, until November 8th 2011, when Bergin’s young driver picked him off. The project was published in November 2011 in print, but was posted online six years later, November 9th, 2017. This is the story of the 2011 mayoral race in Waterbury.)
Story and Photographs By John Murray
At the outset Neil O’Leary's campaign for mayor had the aura of General George Patton storming across Europe at the end of WWII - nobody could stop him.
O’Leary announced his candidacy on February 6th inside a dilapidated store front on East Main Street in downtown Waterbury. During his speech he laid out his platform and rationale for seeking the office of mayor. At the end of his speech O’Leary sang along to Petula Clark’s song “Downtown”, and seemed to be having the time of his life.