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His columns appeared in the Chicago Tribune and were syndicated in 800 papers nationwide. A hard-working and prodigious writer, he delivered five columns a week throughout most of his 33 year career. He was given almost every journalistic award there was, including a 1972 Pulitzer Prize for commentary, the Ernie Pyle Memorial Award, the National Headliner Award, the Heywood Broun Award of the American Newspaper Guild, and the first H.L. Mencken Award presented by the Baltimore Sun. And he was as tough and gritty as the city he wrote about.

Royko considered joining the military. “A couple of my friends went in the Army,” he said, “One went to Europe, drank a lot of beer and met a lot of lovely ladies. Another got as far as Japan.” So, Royko joined the Air Force, was trained as a radio operator and sent to Korea, but eventually, he wound up back near Chicago.

His first break in journalism came when, in order to avoid becoming a military policeman, he convinced an officer to let him work for the base newspaper. “It struck me that any goof could write a newspaper story,” he later recalled.

He lied his way into running the entire paper by saying that he had been a cub reporter for the Chicago Daily News before joining the service. Two weeks later, he was joined at the paper by another serviceman who had been a reporter for UPI. One morning, the man said to Royko, “Don’t con me. You never worked for a newspaper, did you?”

He admitted that the whole thing was a sham, but assigned himself a column anyway.

Royko moved into the private sector and interviewed for a position at the Chicago Daily News, but refused a job offer after looking around the paper and feeling intimidated by the stature of their writers. When Royko returned a year and a half later for another interview, the editor wasn’t interested anymore. The rest of Chicago’s daily papers passed on him because of his lack of college education.

He was eventually hired a few years later by the Daily News to pen lightweight stories at night. During the day, he supplemented his income by selling tombstones over the phone. His articles finally caught the attention of the paper’s editor, who asked Royko what kind of a column he really wanted to do.

“When he asked me that question,” said Royko, “it just sort of clicked together. I said I’d like to be a local columnist.

“I said I’d use satire. There’s a lot of things people have never been told. Straight reporting doesn’t tell it. I felt nobody had ever really described what a City Council meeting was like, what aldermen were like, what a County Board meeting was like.”

By 1964, he was a full-time columnist. He developed a reputation for targeting bigots and crooked politicians while sticking up for the “little guy.” He held Chicago’s self-serving politicians in particularly high disdain and wrote about them frequently: “It’s true that Burke has long been considered the smartest of all aldermen — as well as the best dressed and having the most sleek hairstyles. But it is all relative. Being the smartest alderman in Chicago’s City Council is something like being the tallest midget in the circus.”

His loathe of beaurocracy led him to become an authority on the workings of Chicago’s political machine: “This town was built by great men who demanded that drunkards and harlots be arrested while charging them rent until the cops arrived.”

He became a thorn in the side of local politicians and was accurately described as the “nemesis” of Chicago Mayor Richard Daley. In 1971, Royko wrote a simply-spoken, but scathing depiction of Daley’s political machine called Boss, during a time when Daley was more cautiously feared than revered.

When Royko reflected on Daley at the time of his death, ironically, he could have been talking about himself: “In some ways, he was this town at its best — strong, hard-driving, working feverishly, pushing, building, driven by ambitions so big they seemed Texas-boastful.

“In other ways, he was this city at its worst — arrogant, crude, conniving, ruthless, suspicious, intolerant.

“He wasn’t graceful, suave, witty, or smooth. But, then, this is not Paris or San Francisco.

“He was raucous, sentimental, hot-tempered, practical, simple, devious, big, and powerful. This is, after all, Chicago.”

Maybe the reason Royko understood Daley so well is that they were cut from the same cloth. Both were neighborhood kids who were proud of their blue-collar roots and values. Neither was erudite, but you always knew exactly what they meant.