Two of America's most famous pilots had airmail connections. Before his famous solo flight across the Atlantic in 1927, Charles Lindbergh worked as an airmail pilot on Contract Airmail Route #2 between Chicago, Illinois and St. Louis, Missouri. Amelia Earhart, easily the most famous of the first women aviators, did not work as an airmail pilot, but did carry philatelic mail on some of her flights.
Lindbergh got his nickname, "Lucky Lindy," not from his successful transatlantic flight for which he is famed. Before he tackled the Atlantic Ocean in 1927, Charles Lindbergh had a career as an airmail pilot. Following stints as an Army pilot, test pilot and barnstormer, Lindbergh flew the mail as a contract pilot. His nickname was given to him after he was forced to parachute to safety four different times, including twice as an airmail pilot.
While flying the mail on September 16, 1926, Lindbergh was forced to jump from his plane during a binding snow and rain storm after he had gotten lost in the darkness and his plane ran out of fuel. As he drifted down to earth Lindbergh heard his airplane start back up again.
Apparently as it headed straight down, enough fuel was pumped back into the engine to start it up. A quickly unnerved Lindbergh watched as his airplane seemed to aim straight for him. As Lindbergh wrote up the incident in his official report:
"Soon [my airplane] came into sight, about a quarter mile away and headed in the general direction of my parachute. . . . The plane was making a left spiral of about a mile diameter, and passed approximately 300 yards away from my chute, leaving me on the outside of the circle. I was undecided as to whether the plane or I was descending the more rapidly and glided my chute away from the spiral path of the ship as rapidly as I could. The ship passed completely out of sight, but reappeared in a few seconds, its rate of descent being about the same as that of the parachute. I counted five spirals, each one a little further away than the last, before reaching the top of the fog bank."