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Edwin O'Connor's novel was loosely based on the life of Boston's Irish-American political boss, James M. Curley (1874-1958). Colorful and shrewd, Curley was the four-term Democratic mayor of Boston, the governor of Massachusetts and a two-term Congressman. Even though he was convicted of mail fraud in 1947, he continued to serve as mayor, and in 1950 received a full pardon from President Harry S. Truman. O'Connor's novel was purportedly based on Curley's failed 1949 mayoral campaign.
The publication of the novel generated considerable controversy and a lawsuit. In August 1958, Los Angeles Times reported that Curley filed a lawsuit against Columbia, arguing that the film would constitute an invasion of privacy, as well as damage the prospects of any film adaptation of his autobiography, I'd Do It Again. According to Variety, Columbia argued in court that it had a signed and notarized agreement with Curley releasing the studio from any liability in connection with the film in exchange for $25,000. Curley denied signing the agreement, and both the notary and Curley's agent, James E. Sullivan, to whom the studio made the payment, had disappeared. In its review, Motion Picture Herald Prod Digest pointed out that the two sides later settled the lawsuit out of court.
Hollywood Reporter news items yield the following information about the film: In September 1956, James Cagney was mentioned to star. A March 21, 1958 item noted that veteran producer-director David Butler was to play the part of "Jack Mangan," but had to withdraw because of previous commitments. Although various news items from February-April 1958 place Paul Behrer, Stubby Kruger, Larry Wallace, Harvey Lopez, Snub Pollard, Sam O'Reilly, Irving Schwartz, Rod Gray Eagle, Suzanne Maurer, Sven Thommsen and Hans Gerhardt in the cast, their appearance in the released film has not been confirmed. Jeffrey Hunter was borrowed from Twentieth Century-Fox to appear in the film. Long-time character actor James Gleason (1886-1959) made his final feature film appearance in The Last Hurrah. According to Daily Variety, the film was produced for $2,500,000. Modern sources include James Waters in the cast. O'Connor's novel was also the basis for a 1977 television film of the same name, starring Carroll O'Connor and directed by Vincent Sherman.