The American Legion was chartered and incorporated by Congress in 1919 as a patriotic veterans organization devoted to mutual helpfulness.

   

When local veterans applied for a temporary charter in Winter Garden in April 1920, the post was assigned number 63, simply because it was the 63rd post to be organized in Florida. The permanent charter was effective in August 1921. John C. Bowyer was the first commander.

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The American Legion Post 63 was later named for 1LT Hugh T. Gregory, a Winter Garden resident and first lieutenant in the 3rd Pioneer Infantry of the U.S. Army who was killed in France in December 1920 during World War I. He is buried in the local Oakland Cemetery.

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