This out-of-nowhere quality has been a theme throughout Schultz’s life. When he was a high school quarterback in Norfolk, VA, his singular focus was to become a professional football player—a long shot under the best of circumstances but especially so in Schultz’s case. “He was not a natural athlete,” a high school friend told The Virginian-Pilot in 2004, “but he was a grinder. He was real driven. He always had an idea he was going to be somebody, and he’d work as hard as it took to get there.”

After winning the Division II passing title while quarterbacking for Minnesota State University Moorhead, Schultz fielded calls from NFL scouts and felt a pro career was imminent. But he would have to wait another 30 years before he made it to primetime. In his 2004 book, Straight Talk from the Heartland, Schultz called the NFL draft of 1978, which he watched with high hopes only to be passed over by every team, “the worst experience of my life.” He later signed as a free agent with the Oakland Raiders and, after being cut, briefly played professionally in Canada before taking a final shot with the New York Jets. In 1979, he abandoned his gridiron dream without ever having played a down in the NFL.

Broadcasting was Schultz’s backup plan. When he was a college quarterback, the sports journalists in Moorehead, MN, and Fargo, ND, which is right across the border, realized that Schultz was fairly articulate—a rare commodity on the football field—and encouraged him to someday give broadcasting a try. In the fall of 1979 he did, eventually landing at WDAY, a radio and TV news station in Fargo. As the voice of North Dakota State University football and basketball, he became the most controversial play-by-play announcer in Fargo history, at one point screaming into a live mic before leaping from the broadcast booth to chase after a guy who had thrown a whiskey bottle at him. Over the next decade, as Schultz provided the soundtrack for a rotating cast of obscure college players, Rush Limbaugh was proving that conservative political talk-radio could be at least as entertaining and lucrative a blood sport as football.

Schultz, the guy who had no chance in the NFL but got there, sort of, anyway, was never going to be satisfied on the lower rungs of his new profession. He began to fill in as a talk-radio host on WDAY in 1988, the same year Limbaugh’s show had its national premiere. By 1996, Schultz, now at crosstown rival KFGO, had established himself as the right-wing shock jock of the Great Plains. His favorite targets included the homeless (“how about getting a job?”), the unemployed (“freeloaders”), and farmers (“The American farmer’s hat is bent from being stuck in the mailbox waiting for the government check”).

What came next sounds a bit like the liberal talk-radio version of a superhero-creation myth. In 1998, just two years after starting his talk show, “News and Views,” Schultz met a psychiatric nurse named Wendy Noack, who would become his second wife. Noack worked a second job running a homeless shelter for the city of Fargo, and insisted that Schultz meet her at a soup kitchen on their first date. The experience of eating a baloney sandwich while surrounded by downtrodden men whom he was paid to lambast on the air rattled Schultz’s conservative worldview, and he began what he describes as a period of soul-searching that lasted several years. During this time, he made multiple trips around his coverage area in a 38-foot RV dubbed “The Big Eddie Cruiser,” visiting with struggling farmers and other members of America’s underclass who were largely absent from media coverage during the tech boom of the ’90s. Schultz emerged from this period a changed man.

“I don’t think anyone wakes up one day and says ‘I’m a liberal,’” Schultz admits. “But I underwent a number of grassroots experiences that brought me around to a different perspective.”

Michael Meyer is a CJR staff writer.