In the summer of 1958, then-current IOC president and PASO honorary president Avery Brundage, himself an American, privately said that the Chicago organizers "haven't the faintest idea of the magnitude of the task they have assumed" and predicted that the Games would be "the most dismal fiasco in the history of international sport".

Publicly, he warned that "unless greater effort is put forth to prepare for the 1959 Pan American Games, both the city and the nation may be disgraced in the eyes of the world".

PASO considered cancelling the Games entirely before Chicago's organizing committee was reorganized and Reilly was replaced.

[7][8] President Dwight D. Eisenhower was expected to attend the opening ceremony, but he canceled his appearance in favor of a diplomatic trip to Europe.

[9] On September 7, hours before the closing ceremony, Brazilian rower Ronaldo Duncan Arantes was found dead with bullet wounds at North Central College.

Arantes' brother Rômulo, a fellow athlete at the Games, reported that Ronaldo had brought money to Chicago with him to purchase firearms.