In January 2006, Cutler Bay elected former Florida state legislator John F. Cosgrove as its first mayor. Mayor Cosgrove died on April 19, 2006, while vacationing in Zimbabwe. Vice Mayor Paul Vrooman assumed the position of Mayor. In November 2010, Edward P. MacDougall was elected Mayor from Vice Mayor. Prior to incorporation Edward MacDougall chaired the municipal charter committee which set the Town's charter. In November 2014, Peggy Bell, who was one of the original Council Members when Cutler Bay was incorporated, was elected Mayor and served as Mayor until she reached her term limits in November 2018. Elected in November 2018, the current office of Mayor is held by former Council member Tim Meerbott.