Michael Kinsley once wrote that Simon's writing “balances just about halfway between Hunter Thompson and Theodore White.” In April 1999, Simon was inducted into the Chicago Journalism Hall of Fame. Simon has been a Poynter Media Fellow at
Yale University, a Hoover Media Fellow at
Stanford University, and a
Kennedy School of Government Institute of Politics Fellow at
Harvard University. In 2014 Simon became a fellow at the University of Chicago Institute of Politics. In 2015 Simon won the Dateline Award of the Society of Professional Journalists Washington, D.C. Professional Chapter for Best Column. He was cited for his "thought-provoking writing, storytelling, and interviewing skills" for six columns that included an "extremely prescient analysis of the rioting in Ferguson, Missouri.” In April 2013 Simon won first place in the National Headliner Awards for a series of columns he wrote during the 2012 presidential campaign on the politics of gun control. The Headliner Awards program is one of the oldest and largest annual contests recognizing journalistic merit in the communications industry. Simon has won the award six times. In July 2013, Simon was awarded first place by the National Press Club in winning the Angele Gingras Humor Award. Judges said: "Simon's writing is witty, specific and based on sharp observations of politics and the media." In July 2011 Simon was nominated for an Online Journalism Award in the Commentary / Blogging, Large Site division of the contest. ==Bibliography==