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A Chicago book that holds special meaning to me

Randy Richardson


As a kid growing up in the south suburbs of Chicago, I delivered newspapers at a time when kids still delivered newspapers. At a time when people still read newspapers. And that meant that I read the papers, too. Not the news or the lifestyle or business sections. I read the sports pages and the comics. And I read Royko.

His full name was Mike Royko. But his last name was how we all knew him. As in, “Did you read Royko this morning?” 

His columns for the Chicago Daily News, the Chicago Sun-Times, and the Chicago Tribune were must reading. Every morning you flipped open the paper to read Royko.

Over 30 years, he wrote over 7,500 columns. He was the voice of Chicago. He spoke to the everyman in a plain and simple language that we all understood. He wrote with wit and ferocity and heart.

All of that is what makes Boss, Royko’s 1971 non-fiction book about six-term Chicago mayor Richard J. Daley, his democratic political machine and the City of Chicago during the 1950s and tumultuous 1960s, what Studs Terkel called “a stunning portrait” that “probes not only into the psyche of a neighborhood bully but into the nature of the city that has so honored him.”

Boss is a slim 210 pages but its weight is still tremendous in what it captured about a city then and now. In a retrospective 2012 review in The Huffington Post, Keith Koeneman (biographer of Daley’s son, Richard M. Daley) recommended Boss as “one of the great books of American literature”, saying it “has the qualities of a perfect photograph, capturing the unique essence of a person at a particular – and fleeting – moment in time.”

While Boss did capture a moment in time, it’s hard not to read it today and not see some striking parallels to our city and our country. All of which makes it a timeless classic, one that inspired this former newsboy to become a journalist and a writer who still strives to write like Mike.

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