[1] Simon reported the withdrawal of American troops from Vietnam, the Israeli-Lebanese Conflict in 1982, and the student protests in China's Tiananmen Square in 1989.

Simon later said that it was a "careless mistake" for him and his crew to have crossed the border,[1] and he chronicled the experience in the book Forty Days.

"[2] Similarly, former CBS News anchor Dan Rather said Simon was "one of the best writers ever to work in television journalism.

"[10] He is described by Rather, who worked with him for 38 years, as having been an "old school" journalist, one of the few well-informed "scholar correspondents," and someone who thrived on challenging and dangerous assignments: He didn't just witness history, he strived to understand it.

[10]His numerous award-winning stories during his 47-year career took him throughout the world: He won his fourth Peabody Award along with an Emmy Award for covering the world's only all-black symphony in Africa, and won his 27th Emmy for broadcasting details about an orchestra in Paraguay that could only afford to make their instruments out of trash.

[3] War zone stories covered by Simon include conflicts in Portugal, Cyprus, the Falkland Islands, the Persian Gulf, Yugoslavia, Grenada, Somalia, and Haiti.

[11] On February 11, 2015, Simon was discovered unconscious with severe head injuries in a car crash on the West Side Highway of Manhattan, New York.

Simon was extracted from the roof of the limo by rescue workers and transported to St. Luke's–Roosevelt Hospital, where he died a short time later.

He would win yet another Emmy Award with his reporting about an orchestra in Paraguay whose poor members constructed instruments from the trash retrieved from a local landfill.

He was a four-time recipient of the Overseas Press Club's highest honor for a body of work, the President's Award.