Charlie Sykes has certainly shaped Wisconsin politics. There was a moment, starting in 2010, when the state turned from blue to red. Scott Walker took the governor’s office, Paul Ryan would go on to become speaker of the House of Representatives, Reince Priebus would lead the Republican National Committee, and The Bradley Foundation based its operations in Milwaukee. It was a time when southeastern Wisconsin was “a vibrant hub of conservative ideas and leadership,” according to Charlie, who was in the thick of right-leaning circles of influence then, best known as the longtime conservative talk show host on WTMJ radio. Fast-forward a few years. Charlie was part of a conservative backlash against the campaign of Donald Trump that went largely unnoticed by the broader media world until the day Trump called into his radio program. Those 17 minutes of radio sparked national media interest, giving Charlie a higher national profile as a “Never Trump” conservative. Suddenly, The New York Times, MSNBC and The Atlantic came calling, hoping to hear his perspective. Not long after his fateful call with the would-be president, and after 23 years on the airwaves, Charlie stepped down from his top-rated show. He wrote a book, one of nine he’s written over the years, called “How the Right Lost Its Mind” (St. Martin’s Press, 2017), and, in 2018 founded The Bulwark, a news network that provides political analysis described as “conservative, conscientious and civil.” In recent years, he’s continued to write for national publications and appear on TV. He has some regrets about the damage he did with his squawk box, including to local journalism, though he has choice words for local media, which he considers often smug and not prone to self-critique. He got his own start covering City Hall for The Milwaukee Journal, and it may surprise some people to learn that he was once a Democrat. He helped his father with Eugene McCarthy’s campaign and attended the 1968 convention in Chicago as a page. He even ran for Congress against Rep. James Sensenbrenner as a pro-life Democrat when he was at UWM.