Half a century of presidential campaign buses, from Jimmy Carter's in 1976 through Barack Obama's, shaped the byline of Roger Simon, the only journalist to win the American Society of Newspaper Editors' Distinguished Writing Award for commentary twice. He died on September 10, 2026, in Washington, D.C., at 78, the Washington Post reported.

Simon grew up in Chicago's South Shore neighborhood, by his own account living about ten blocks from the house where he was born, according to a 2014 WTTW profile done during a fellowship at the University of Chicago's Institute of Politics. From 1966 to 1970 he served as campus editor and then executive editor of the Daily Illini, the student paper at the University of Illinois at Urbana-Champaign, where he graduated with a bachelor's degree in English. Before Chicago's daily papers would have him, he worked at the Danville Commercial-News, the Waukegan News-Sun, and the City News Bureau of Chicago, the wire service that trained generations of the city's reporters.

In 1972, Simon joined the Chicago Sun-Times, where he spent twelve years as an investigative reporter and columnist. He reported from South Africa under apartheid and from Lebanon during the Israeli invasion, covered the O.J. Simpson trial, and secured an exclusive interview with convicted killer John Wayne Gacy, according to Creators Syndicate, which later syndicated his column nationally. Those assignments forged the combination of persistence and humor that would mark his writing for the rest of his career.

He moved to the Baltimore Sun in 1984 and wrote a staff column there for eleven years. His book Road Show followed the 1988 presidential race. In 1998, while covering the White House for the Chicago Tribune through the Monica Lewinsky scandal, he published Show Time, an account of the 1996 campaign that became a New York Times bestseller.

Simon became chief political correspondent, and later political editor, of U.S. News & World Report starting in 1999, the same year Chicago inducted him into its Journalism Hall of Fame alongside his wife, Marcia Kramer, herself a longtime editor who had served as a copy desk chief at the Washington Post. His book Divided We Stand examined the contested 2000 election.

In January 2006, Simon became Bloomberg News' first chief political correspondent. He later moved to the new political website Politico as its first chief political columnist, the post he would hold longest. Across his career he covered every presidential campaign and nominating convention since 1976 and interviewed every president from Jimmy Carter to Barack Obama, amassing more than three dozen first-place journalism awards, six National Headliner Awards, and three Silver Gavel Awards from the American Bar Association. Harvard's Institute of Politics, which named him a fellow in 2005, later noted that he had also become a familiar face on network television, appearing on Meet the Press, the Today show, Good Morning America, Larry King Live, and Charlie Rose. He held further fellowships at Stanford's Hoover Institution, Yale's Poynter program, and, in 2014, the University of Chicago's Institute of Politics. In 2013 he published Reckoning, his account of that year's campaign, and the National Press Club gave him its Angele Gingras Humor Award. The Society of Professional Journalists awarded him its Dateline Award in 2015.

Simon announced his retirement from Politico in January 2017, closing out the job at 68. In his final column, published February 1, 2017, in Politico, he wrote, "This is the end, my friends. It is time to say goodbye," and explained that he was leaving on his own terms: "I leave the writing of a regular column entirely voluntarily. No editor hung a dead chicken over my doorway." He called the work "a terrific job. A job of spectacular fun and deep satisfaction," though he said he had no wish to "have my corpse discovered one late night draped over my keyboard."

Six weeks later, Simon returned to print, writing a monthly freelance column for the Chicago Sun-Times, the paper where his career had started four decades before. He still had family in Chicago decades after his reporting had moved permanently to Washington, according to the same WTTW profile.

Dan Balz, who covered national politics in Washington alongside him for decades, opened his Washington Post tribute by writing, "There was no one like Roger Simon. That's said about a lot of people, but in Roger's case, it happened to be true." The newspaper's headline remembered him for his toughness and his wit.

Simon left five books, four of them chronicles of the presidential campaigns he covered firsthand, a career that ran through newsrooms in Chicago, Baltimore and Washington, and an ASNE commentary award that, years after he won it twice, still belongs to no one else. His wife, Marcia Kramer, survived him. Reporters who followed him onto the campaign bus inherited his standard: that the absurdities of American politics could be covered with rigor, and without losing a sense of humor about them.