One of my favorite writing anecdotes is Mike Royko’s tale of finishing Boss^•, from Doug Moe’s The World of Mike Royko:

He typed the last page of Boss late on a Saturday afternoon in 1970 in his office at the Daily News. Royko pulled the page from the typewriter, put it under the others in the large stack, and walked to Riccardo’s, a restaurant and bar on Rush Street near the newspapers. The bar was quiet and Royko ordered a martini, not his usual drink of choice. This was, after all, quite a moment.

The bartender, who knew him, said, “What’s going on, Mike? Celebrating?”

“I guess so,” Royko said. “I just finished a book.”

“Yeah?” the bartender said. “Me, too.” He reached under the bar and handed Royko a paperback. “You can read it. It’s by Mickey Spillane.”

Well, I’ve just finished a book, too: I’ve finally read Boss^•. It’s the story of Chicago mayor Richard J. Daley’s rise and reign. It is a very Chicago story, but some of the more interesting parts are where Daley’s story intersects with the national Democratic Party’s story. For example, Daley’s ability to deliver votes got him the 1968 Democratic National Convention. His ability to overreact got him—and the Party—the 1968 Democratic National Convention riots. And Daley’s overreaction to the problems caused by his own overreaction got them all bad publicity.

Daley understood how to win by building a machine; he didn’t understand—or just didn’t care—what the machine looked like to outsiders. Royko is almost certainly invoking Animal Farm when he describes Daley’s response to opposition inside the convention hall. I’ve heard some of the convention on audio from the time, and had assumed that the mad ranting audible in the hall was because the rioters were right outside the gates. Turns out, the mad ranting came from Daley. When the other Democrats started making proposals to condemn Daley for his handling of the protests, Daley got his aldermen to bring in supporters, and when an outsider started going off on a tangent Daley didn’t like he signaled them to start yelling praises to him.

It was blunt and blatant. Compare to today, when the press, as President Obama’s popularity wanes, goes into a frenzy over fringe bloggers and Obama birtherism without noting the press’s own foray into the even more ridiculous Trig birtherism emanating from “respected” organizations like the Atlantic.

The 1968 convention pushed Daley into the national spotlight in a bad way; Royko, whose writing would probably have garnered national attention anyway in a few years, was pulled along with him. This book was the result. Royko was, however, already Daley’s adversary when he started writing the book. He’d taken on the mayor several times in his column for the Daily News.

Somebody had to do it… I was his number one adversary. I’d like to be in that position. Running a city and some meatball on a newspaper is the only guy I have to worry about. He didn’t have to worry about who ran against him. Why do you want to climb Mt. Everest? Because it’s there. He was there. — Mike Royko (The World of Mike Royko)

Royko spent two years researching, and interviewing Mayor Daley’s old acquaintances and rivals, to build this character study of the entrenched Chicago mayor. Royko is best known as a columnist, but he started work as a non-bylined reporter in the famously tough City News Bureau. Boss tones down the Royko snark in favor of the research he learned employed by editors such as Arnold Dornfield at City News. Royko’s reporting, like Woodward and Bernstein’s, looks easier than it is. People forget that before he wrote daily columns about whoever needed poking that day he was a News Bureau reporter. He kept the News Bureau work ethic even after he switched to being a columnist. Unless you also read his biographies you don’t get how much work went into ensuring that his satire was accurate where he wanted it to be. It’s easy to look at a readable, friendly work like Boss and not see the work that went into it.

F. Richard Ciccone wrote about City News in A Life in Print:

CNB… reports were terse and factual. It was Dornfield’s customary advice to young reporters that became a legend in American newsrooms: “If your mother says she loves you, check it out.”

City News was the toughest boot camp in journalism. Reporters were badgered to find out everything. One recalled being screamed at for not knowing the color of a dead infant’s eyes. Reporters were sent back to crime scenes over and over until they got every detail.

One CNB veteran recalled covering the death of a child who choked on a tree ornament on Christmas Eve. “I thought I had it all wrapped up but the desk made me call the family back: What color was the ornament your baby choked on?”

Royko began like everyone else on cops and courts, chasing minor arrests and verdicts, learning to get every name and address right, checking street directories and telephone books to verify the information, and enduring the harassing questions of the desk. He mastered the art of having the answer to every possible question.

He built contacts and learned how justice worked. What he learned at City News—the machine on which Chicago ran—helped him writing Boss. The result is an engaging story of Chicago-style politics in the forties, fifties, and sixties.

The lessons of Boss are not out of date. Some of what Royko describes is frightening in its familiarity. Our recent fiasco with car dealerships, the billion-dollar payout to auto unions, the trillion-dollar payout to various Democratic groups, all look a lot like Chicago politics taken national. It’s like someone is setting up Daley’s machine in Washington.

I’ve written before, for example, about how government-union dues are a way of laundering tax money into lobbying for expansion of government programs. Daley’s machine had that down: patronage workers were required to put 2% of their wages right into ward coffers, where it was used to generate more votes for the machine.

Daley also understood the principles I’ve written about when I say to vote for nobody: that people whose votes you can count on aren’t important. “He figured he’d always get the black vote, but the whites had already shown that they’d go for somebody else when they went for Adamowski.”

And he understood the usefulness of myriad laws, rarely enforced. In his case, it was strict building codes that only ever seemed to be enforced against property owners who criticized Daley. Daley used them to club property owners into accepting segregated neighborhoods, such as when John Walsh tried to rent an apartment in Daley’s neighborhood to two black students. It worked because of two sets of restrictive laws:

1. The owner needed to hire a real estate agent to handle rentals and the real estate agent required a license from the city. “The real estate man who handled the move-in was summoned by the ward organization and told what to do. He listened because real estate licenses are under the control of the mayor of the city of Chicago. They told him that the two black youths were no longer tenants in the building; that two white men from the neighborhood were going to move in and were going to be given a long, unbreakable lease for the apartment, and that it was all going to happen immediately.”
2. Rarely-enforced building codes can bankrupt property owners. “When John Walsh got home that night, he found that he owned a three-flat with white tenants and all of them had unbreakable leases. Walsh soon sold the building. If he hadn’t, he would have gone broke trying to meet the city building department’s demands for improvements. Chicago has one of the nation’s strictest building codes. Although rarely enforced, it provides City Hall with a powerful club over property owners.”

Broad laws are easily used to harass political opponents, and unused laws are still a threat to freedom.

Before the ’68 Democratic convention riots, there were riots when the Reverend Martin Luther King, Jr. died. Daley told the press that the police should be instructed to “shoot arsonists and looters—arsonists to kill and looters to maim”. A few days later, Daley backpedaled from that statement, claiming it was a misunderstanding. His press aide blamed the misunderstanding on the press. “It was damn bad reporting. They should have printed what he meant, not what he said.”

I suspect Royko loved this line; he used it again later, such as in his February 16, 1973 column “What’s Behind Daley’s Words?”. But that’s what newspapers did in the fifties and sixties. In Daley’s mind, it probably wasn’t unreasonable for him to expect that deference. Times changed, although sometimes I worry that they’re changing back.

Through this, Royko identified as a Democrat. Boss was more of a reform work than a cry against the overall idea of Democratic supremacy. You can see it in how he describes the Republican leadership in Chicago. On pages 174-175, he describes them as “right wing” when they help Daley, and “conservatives” when they help peace marchers. In Royko’s lexicon, what makes conservatives “ultra-right” is… supporting Chicago Democrats. In his defense, it must have been difficult to define partisan boundaries in a city where Republican businessmen donated to Chicago ward bosses to stay in business, and Republican newspapers forced Republican candidates to lay off the Democratic Mayor’s construction graft, because they were a part of it, too. This is what happens when the government controls every aspect of life: everyone rushes to please the people in power, resulting in the people in power staying in power.

Ultimately, that’s what this book is about. That power is often self-perpetuating doesn’t make it right. Boss is a fascinating glimpse at a past that we could easily fall into again. I recommend reading it.