Since the Massachusetts Bay Colony was established, Boston has been described as a “city on a hill” or a city to be looked to as an example for others. President Kennedy drew from the same material when he left for Washington D.C. In this episode, we look back at some of Boston's notable mayors who left their mark on the original “city on a hill” including President Kennedy's grandfather, John Fitzgerald. We also look ahead to Boston’s future under new mayor Michelle Wu.