Simon died of pneumonia at MedStar Washington Hospital Center in Washington, D.C., according to his obituary. His death ended a journalism career that took him from Chicago newspapers to national political coverage and eventually to Politico, where he served as chief political columnist.
Simon grew up in Chicago and attended the University of Illinois, where he studied English and worked for the student newspaper, the Daily Illini. He met fellow student Marcia Kramer there. The two later married and remained together for nearly five decades.
After college, Simon began his newspaper career in Illinois. He joined the Chicago Sun-Times and became an investigative reporter and columnist. He tackled political corruption, racism, and social issues, including domestic violence. His reporting on spousal abuse helped prompt the Chicago Police Department to change how it classified such incidents.
The Sun-Times assigned Simon to cover the 1976 presidential campaign. He continued covering presidential elections and nominating conventions for the next 40 years. During that span, he interviewed presidents from Jimmy Carter through Barack Obama and reported from campaigns across the country.
Simon also wrote several books about presidential politics, including Road Show, Show Time, Divided We Stand, and Reckoning. His writing combined political reporting with humor and an accessible style that brought complicated campaigns to a broad readership.
After leaving the Sun-Times in 1984, Simon worked for U.S. News & World Report and Bloomberg News. He later joined Politico as its first chief political columnist. He also returned to the Chicago Sun-Times as a columnist after ending his Politico tenure.
Washington Post journalist Dan Balz, who met Simon while they both worked at the University of Illinois, remembered him as an original journalist and a craftsman. Balz recalled traveling with Simon to political events over several decades and praised his toughness, wit, and reporting skill.
Simon leaves behind his wife, Marcia Kramer Simon, along with other family members.