Pictures Curley alongside President Franklin Roosevelt.

Boston mayor James M. Curley rode the president's coattails into the governor's mansion in 1934, having failed in a previous bid 10 years earlier. A populist Democrat with roots in the Irish working class, Curley was a firm backer of the New Deal, but his brash political style clashed with FDR's patrician sensibilities, and the two were never close allies. A series of scandals caused Roosevelt to withold his support for Curley in his 1936 Senate bid, but Curley would mount a comeback in 1942, winning a seat in Congress, where he was a strong supporter of Roosevelt's social agenda. Coming full circle, after leaving Washington, he would be elected to a fourth term as mayor of Boston.

A classic Depression-era pinback, priced well under guide.