Complex sentence: He held the Aero Club of America's pilot's certificate No.7, issued in 1907, and was the first passenger to fly in an airplane from New York to Washington, D.C. in May of 1916.
Split into simpler sentences: He held the Aero Club of America's pilot's certificate No.7, issued in 1907. He was the first passenger to fly in an airplane from New York to Washington, D.C. in May of 1916.