Who is the most notorious of all city bosses?

The most notorious city boss in American history is often considered to be Boss Tweed, the leader of Tammany Hall in New York City during the mid-19th century. Known for his corrupt practices, Tweed exploited his political power for personal gain, overseeing massive fraud schemes that cost the city millions. His reign came to an end when he was convicted of corruption in the early 1870s, but his legacy remains a symbol of political corruption in urban governance.