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Men began jumping from hot air balloons and tall buildings with the aid of parachutes in the late 1700s. They all landed, though some did so far faster than planned. Still, parachute technologies improved over the next century until men jumping from hot air balloons was safe enough to be featured at county and state fairs. Still, the risk of death or dismemberment remained high enough to attract a crowd.
Many of the fairs featuring death-defying acts also included football games and other athletic contests, so the first entangling of parachuting and football likely came at some long-forgotten fair. Parachuting at fairs became more common after the development of heavier-than-air machines, and the poor safety record of aeroplanes made the development of better parachutes all the more critical. Even expert pilots like Charles Lindbergh had bailed out four times before he tried crossing the Atlantic. At the same time, Congressman Phil D. Ewing of San Diego pushed for a law requiring commercial airlines to provide parachutes for passengers and crews. (Imagine boarding a commercial airliner considered so unreliable that they issued parachutes to passengers.)
Perhaps it was the fact that football and parachuting were exciting and involved a level of danger, but the two have hung out for some time. The first instance of parachutists dropping directly onto a football field appears to have come in 1918 at Fort Omaha, where the Army had its balloon training school. During a game with the St. Paul Aviation Mechanics School, the balloonists dropped footballs before the game and sent ten men overboard at halftime in a race in which the winner was the last man to touch down.

After WWI, dropping footballs from balloons and airplanes became a relatively common occurrence, especially after they realized the balls' survivability increased when attached to tiny parachutes before dropping a few thousand feet onto the gridiron. Parachuted balls fell at the 1926 Earlham-Hanover game, but ball parachuting reached its zenith at the 1929 Florida-Oregon game at Madison Square Garden near Miami. Attendees saw two teams of high school girls competing to catch a ball dropped from the Defender, a Goodyear dirigible flying over the stadium.

People also began parachuting into football stadiums during the 1920s. A 1928 game between Chico and Gridley high schools in California included the unplanned appearance of a woman jumper who landed on the right side of the offensive line as a play started. Others dropped for a $100 prize at the Selma Fireman-Fresno Elks game the same year.
Of course, not everyone that dropped hit the mark. Kim Scribmer, a Maryland freshman, was scheduled to parachute onto the football field at halftime of a 1936 game but missed and was hung up on telephone wires. Santa Claus jumped from his flying sleigh during halftime of the December 1947 Redskins-Boston Yanks game at Griffith Stadium but missed and landed on a more familiar location, the rooftop of a nearby house.
Any number of well-trained WWII paratroopers jumped out of planes in the 1940s and 1950s and began hitting the mark, raising the bar for all jumpers. Still, the high bar for attempted jumps came in 1964 when Cosmo, the BYU mascot, scheduled a jump into BYU's new stadium before their game with New Mexico. Unfortunately, Cosmo did not arrive at the stadium until partway through the first half. He was fully costumed as planned, with tree branches caught in his harness.
The development of ram air or pillow parachutes in the early 1960s dramatically increased parachutists’ ability to steer and slow their descent, giving them far greater ability to land softly on the target football field. Skydiving into stadiums became more accurate and familiar, though that does not always work out in practice. I attended the 2017 Wisconsin-BYU game in which the skydiver seen in the following video hit the wall. Seemingly uninjured, it reminds us why our ancestors were thrilled by parachutists dropping into games of old.
Navy parachutist crashes into wall at 2017 Wisconsin @ BYU game
BYU's Cosmo parachutes into a BYU practice in 2022
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