The American Legion, established by Congress in 1919, is a patriotic veterans organization committed to mutual support. In April 1920, local veterans in Winter Garden applied for a temporary charter, designated as Post 63, marking it as the 63rd post in Florida. The permanent charter was granted in August 1921, with John C. Bowyer serving as the first commander. Later, the post was named in honor of 1LT Hugh T. Gregory, a Winter Garden resident and U.S. Army first lieutenant who perished in France in December 1920 during World War I, and rests in Oakland Cemetery.
