Chiappone began his career in politics in 1994, when he produced a local Public-access television program called "Bayonne Sunnyside Up," which focused on the community events that take place in Bayonne. Chiappone then created the community action program, "Bayonne Public Forum." Through this Government-access television (GATV) venue, he televised meetings of the Bayonne Municipal Council, Hudson County Board of Chosen Freeholders, local school board meetings and Bayonne Zoning & Planning Board meetings. It was through this civic participation that Chiappone became involved in local government and politics. Chiappone at that time created the civic activist watchdog group called REACT (REsponsible ACTion in Government). As an Independent municipal candidate in 2002 having defeated the Council candidates of his political adversary Bayonne Mayor and Assemblyman of the 31st District Joseph V. Doria, Chiappone was selected by then Jersey City Mayor Glenn D. Cunningham to run on his legislative team in the 31st District. Along with Lou Manzo, Chiappone and Glenn Cunningham defeated Joe Doria's 31st District Democratic team of Joseph V. Doria, L. Harvey Smith and Elba Perez-Cinciarelli in the June 2003 Primary election. Following the death of Glenn Cunningham, Chiappone ran unsuccessfully for Senate against Joseph V. Doria in the Special election to fill the vacancy in November 2004. Chiappone was then defeated in the Democratic Primary in June 2005 by the team of Louis Manzo and Jersey City Superintendent Charles T. Epps, Jr. After once again defeating "Team Doria" for the non-partisan 2006 Bayonne municipal election for the position of Councilman At-Large, Chiappone aligned himself with the wife of deceased Glenn Cunningham, Sandra Bolden Cunningham, to once again seek state legislative office in the 31st District. Along with running-mate L. Harvey Smith, Chiappone defeated the team of Nicholas Chiaravrolloti and Sheila Moses-Newton for Assembly in the Democratic primary in 2007, thus essentially winning the election as they were running unopposed in the general election. Chiappone and Smith were sworn in as Assemblyman in January 2008.