Roosevelt attended the 1924 Democratic National Convention where he served, in his words, as his father's "page and prop". In 1928, he and some Harvard classmates campaigned for Democratic Presidential nominee Al Smith. In 1932, he headed FDR's Massachusetts campaign; he made about two hundred campaign speeches that year. Though FDR lost the Massachusetts Democratic primary (to Smith), he easily carried Massachusetts in the November election. James Roosevelt was viewed as his father's political deputy in Massachusetts, allocating patronage in alliance with Boston mayor James Michael Curley. He was also a delegate from Massachusetts to the Constitutional Convention for the repeal of Prohibition in 1933.  Roosevelt was a close protege of Joseph P. Kennedy Sr.. In 1934, the two journeyed to England to obtain the market in post-prohibition liquor imports. Many of Roosevelt's controversial business ventures were aided by Kennedy, including his maritime insurance interests, and the National Grain Yeast Corp. affair (1933-35). Treasury Secretary Henry Morgenthau, Jr. threatened to resign unless FDR forced James to leave the latter company, suspected of being a front for bootlegging. James Roosevelt was instrumental in securing Kennedy's appointment as ambassador to the United Kingdom.  In April 1936, Presidential Secretary Louis Howe died. James Roosevelt unofficially assumed Howe's duties. Soon after the 1936 re-election of FDR, James Roosevelt was given a direct commission as a lieutenant colonel in the Marine Corps, which caused public controversy for its obvious political implications. He accompanied his father to the Inter-American Conference at Buenos Aires in December as a military aide. On January 6, 1937, he was officially appointed "administrative assistant to the President"; on July 1, 1937, he was appointed Secretary to the President. He became White House coordinator for eighteen federal agencies in October 1937.  James Roosevelt was considered among his father's most important counselors. Time magazine suggested he might be considered "Assistant President of the United States".  In July 1938, there were allegations that James Roosevelt had used his political position to steer lucrative business to his insurance firm. He had to publish his income tax returns and denied these allegations in an NBC broadcast and an interview in Collier's magazine. This became known as the Jimmy's Got It affair after Alva Johnston's reportage in the Saturday Evening Post. Roosevelt resigned from his White House position in November 1938.

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