Hailed as one of Boston’s most beloved mayors and its longest serving, Thomas Menino (1942–2014) deftly managed the city’s finances and transformed Boston into the hub of innovation that it is today. During his time in office, Boston embraced modern industrial growth and moved forward with noteworthy developments that altered neighborhoods, while also facing ongoing racial strife, challenges of unaffordable housing, and significant public union negotiations. Mayors in modern American cities occupy unique positions as government leaders who need to remain active parts of their communities in addition to being tasked with fixing neighborhood issues, managing crises, and keeping schools and public infrastructure on course. Situating news coverage alongside interviews with the mayor and his administration, political scientist Wilbur C. Rich chronicles Menino’s time in office while also considering his personal and professional background, his larger-than-life personality, and his ambitions. Menino’s approach to these challenges and opportunities offers enduring lessons to anyone interested in urban government and political leadership.