Charles Keeney Hamilton – Connecticut’s ‘Crazy Man of the Air’

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In 1910, two newspapers, one in New York and the other in Philadelphia, put up a prize of $10,000 for the first pilot who could fly from one city to the other and back. Charles Keeney Hamilton, one of the most famous stunt pilots of the day, won it.

It was probably the most notable prize of Hamilton’s career, but what he was best known for was crashing.

Hamilton, by some estimates, crashed as many as 60 times over his 11-year flying career. He broke most of his bones and often gave the doctors who put him back together a good challenge.

Yet time and again he would head back to whatever plane was handy and go back to the flying.

Charles Keeney Hamilton

Born in 1885 in New Britain, Conn., Hamilton took to flying at an early age, first in lighter-than-air dirigibles, balloons, kites and blimps. But he soon realized that heavier-than-air flying machines were capturing the public’s fascination. The air shows of Europe offered crowds thrilling races and competitions such as slow-flying or quick take-offs.

Hamilton signed on with early aviator Glenn Curtiss as part of Curtiss’ stunt-flying show, and he leased a plane from Curtiss. The two parted ways over a dispute over the lease payments on the plane and how big a share of his winnings Hamilton should pay Curtiss.

Hamilton replaced the Curtiss with his own custom-made plane, a 110-horsepower crate he called the Hamiltonian. He traveled from one end of the country to the other, sometimes joining in air shows and other times doing solo demonstrations.

In 1909 and 1910, crowds were thrilled by the air shows, but very quickly the novelty of watching a plane fly wore off. The aviators had to add spice to their shows, and Hamilton proved masterful. He would push his plane high into the air and then, giving the appearance that his engine had cut out. The he dove toward the ground while the crowds shrieked.

Then, with polished timing, he would pull the craft out of the dive to everyone’s relief. At least, that’s what was supposed to happen. On occasion, Hamilton would miscalculate or his engine would fail during a show, and his plane would land in a heap.

Hamilton was also known as a heavy drinker (and chain smoker) who sometimes flew under the influence. That added an element of danger to the airshows as planes raced each other or sometimes automobiles.

Bird Men

Crashes were not the brutal and explosive events of modern times, but they were no picnic. The pilot was often battered by pieces of the plane’s fuselage, scalded by radiator fluid or just smashed into the ground.

Still, the daring aviators, known as ‘Bird men,’ were the stars of their day. Hamilton was branded “The Crazy Man of the Air” for his fearless flying, which once landed him in a lake in Washington state in front of an awestruck crowd.

He received a hero’s welcome in 1910 when he returned to New Britain, Conn. There he gave New Englanders their first demonstration of an airplane.

In total, Hamilton earned a quarter of a million dollars with his stunt flying by the end of 1913, but he kept very little of it. In January of 1914, the inevitable happened. Charles K. Hamilton died. Not in an airplane, but from tuberculosis.

If you enjoyed this story, you might want to read about Ruth Law here, or New Hampshire’s Bob Fogg here. This story updated in 2022.