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In 1912 Messer bought a Curtiss-type biplane, powered by a Kemp engine, at a sheriff's sale in Kansas City, Missouri. With this plane he flew some exhibition dates that year but had considerable engine trouble, so he installed a Gnome rotary engine. He did some exhibition flying through 1912-1915 and during that period installed a Curtiss OX-2 engine. 

Out of college in 1916, Messer joined the Royal Flying Corps and served in England and France. When America entered the war he returned to the United States, accepting a commission in the Aviation Section of the Signal Corps, and was assigned as an instructor at Kelly Field, Texas. Also there were Eddie Stinson and several other early pilots. When a Royal Flying Corps mission came there, Messer was transferred to their group to teach the gosport system of communication. This system used a mouthpiece for the flight instructor connected by rubber tubes to cups that fit over the student's ears. It was far better than trying to out-shout the noisy engine. The gosport system also employed a proven method of instruction sequence. On this duty Messer was sent to several flight-training fields, and then returned to Kelly. 

Meanwhile he was assigned to the original airmail operation that was begun on May 15, 1918, between Washington, Philadelphia, and New York. It was the world's first  airmail conducted as a continuous public service on a schedule between fixed stations, the beginning of airmail as we know it today. 

Messer flew a Curtiss "R" mail plane. This was a tractor biplane, larger than the JN-$H or JN-6H types with which the service was started. The "R" was powered with the 400 [strikethrough]horsepower[//strikethrough] h.p., Liberty engine and could carry more gasoline and about 400 pounds of mail. Messer's flight was efficiently flown, arriving on schedule, taking about two and one-half hours for the 218-mile route.

In the summer of 1919 Messer received an honorable discharge from the Army and formed a partnership with Edward Stinson to operate a new flying field at Birmingham, Alabama. With Stinson managing the field, Messer formed the