James Michael Curley was the 41st, 43rd, 45th, and 48th Mayor of Boston. Corrupt but able to get things done, he was actually elected to his fourth term while being indicted for actions taken during his previous terms. He more or less governed from prison. I'm most impressed with the fact that when he was denied a spot as a party delegate from MA he became a delegate from Puerto Rico under an assumed name. That's some balls, right there.
The lyric in the chorus "The Last hurrah" is the title of a film based on his life. The lyric "I'd do it again" is the title of his autobiography.