Walter "Eckie" Eckersall was one of the most famous people in Chicago for three decades: He was the city's first high school athlete superstar when the competitive prep athletics scene was maturing in Illinois, then quarterback of the University of Chicago Maroons, and finally a prominent sports journalist for the Chicago Tribune. As the greatest player in the University of Chicago's history, Eckersall led the Maroons to a national title in 1905 and earned a place as an All-American three times. Head coach Amos Alonzo Stagg and Eckersall helped set the Maroons on a two-decade path of excellence that made football the biggest and best game in town. As American sports entered a golden age and journalism was revolutionized by advancements in printing technology, Eckersall entered the growing field of sports journalism. He became the lead sportswriter for the Chicago Tribune and the lens through which many Chicagoans understood sports. During his twenty-three-year career, he covered and promoted many of the greatest athletes and sporting events, including the inaugural Indianapolis 500, the Dempsey-Tunney Long Count fight, eleven Rose Bowls, and strange gambling patterns that eventually exposed the 1919 Black Sox scandal. While Eckersall was a great player and well-known writer, he had many flaws, some unknown to the public for decades. He was expelled after his last game with the Maroons, was caught committing theft, secretly eloped in a shotgun wedding and then soon abandoned his wife and young daughter, and struggled with a drinking problem. But he was also notably generous and a vocal and consistent supporter of equal opportunity for Black athletes. Chris Serb's biography sheds new light on Eckersall's long-forgotten career in the context of Chicago's burgeoning sports scene.