Summary: President Woodrow Wilson issued a proclamation in 1916, establishing June 14 as Flag Day. President Harry Truman made it official in 1949 when he signed legislation designating June 14 of each year as National Flag Day. … One-year retrospective: One year ago today, on June 14, 2009 Aubrey Immelman provided his weekly report of U.S. military deaths in Operation Iraqi Freedom and Operation Enduring Freedom (Afghanistan), compiled from U.S. Department of Defense News Releases.