Ryan's professional journey started in journalism. While still in college, he served as a sports correspondent for the Chicago Tribune, and after graduating, he joined the paper’s newsroom as a full-fledged reporter. In 1922, he became a sports columnist for the Herald-Examiner and simultaneously experimented with one of the earliest forms of scripted radio content in Chicago — a poetic radio continuity segment he both wrote and read on-air.
In 1924, Ryan took on multiple roles at WLS, which was then owned by Sears, Roebuck. That same year, when the Chicago Tribune purchased WDAP and rebranded it as WGN, Ryan signed on with the station. He joined a staff that included future radio greats Sen Kaney and Jack Nelson. Ryan quickly rose to prominence, becoming station manager in 1924 and again in 1931, a post he held through much of WGN's formative years.
Known for his versatility, Ryan was both a commanding presence behind the microphone and an agile administrator behind the scenes. He was the first radio announcer to provide live coverage of the Kentucky Derby and a regular season baseball game, opening the door for future sports broadcasting. His baseball credentials extended even further when he was selected by Judge Kenesaw Mountain Landis, alongside Graham McNamee, to broadcast the first World Series over a connected network of stations — a major step in the nationalization of America's pastime.
Ryan’s voice was familiar to millions, not just for baseball, but also for some of the most memorable events of the 1920s and 1930s. He delivered play-by-play commentary as Red Grange scored four touchdowns in 12 minutes against Michigan, reported from the Scopes “Monkey” Trial, and covered both the Democratic and Republican National Conventions of 1928. He was behind the mic for the Dempsey-Tunney prizefights, the Memorial Day 500 auto race, and breaking news stories such as the Chicago Stock Yards fire, the Knute Rockne funeral, and the sinking of the excursion steamer Favorite off Oak Street Beach.
Known to younger listeners as “Uncle Quin” from his work on children's programs like Little Orphan Annie, Ryan brought warmth and credibility to every broadcast. His career blended reporting, entertainment, and technical innovation, establishing him as one of early radio’s most influential figures.
In February 1931, Ryan married Roberta Nangle, a member of the Tribune’s society staff. He continued to serve WGN for decades, helping the station maintain its status as a leader in American broadcasting.
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