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In 1940, Colonel Frank Knox, newly appointed by President Franklin D. Roosevelt as Secretary of the Navy, offered Stevenson a position as Principal Attorney and special assistant.
In this capacity, Stevenson wrote speeches, represented Secretary Knox and the Navy on committees, toured the various theaters of war, and handled many administrative duties.
Since Knox was largely a figurehead, there were few major roles for Stevenson, However, in early 1944 he joined a mission to Sicily and Italy for the Foreign Economic Administration to report on the country's economy.
After Knox died in April 1944, Stevenson returned to Chicago where he attempted to purchase Knox's controlling interest in the Chicago Daily News, but his syndicate was outbid by another party.

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