Kelly was born in 1882 in Xenia, Ohio and studied at the University of Michigan (1900–1902). He began his newspaper career in 1896 as a local correspondent for a small town newspaper and wrote a humor column for The Plain Dealer (Cleveland, Ohio) for five years. His "Statesmen, Real and Near" column (1910–1918) was the first Washington, D.C. news column to be syndicated. During World War I, Kelly served briefly as special agent for the Federal Bureau of Investigation.
After the war Kelly bought and operated a farm in Peninsula, Ohio where he continued to support himself as a free-lance writer. In addition to his journalistic work, he was the official biographer of the Wright brothers, and worked to bring the original 1903 Wright Flyer home to the U.S. from the Science Museum in London, to which Orville Wright lent it during his long feud with the Smithsonian Institution over credit for the first flight.
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