The Chicago Police Riot
By: Sal Maiorana
Tags: Politics, Chicago Police Riot, Historical Fiction

1968 — A HISTORICAL NOVEL: CHAPTER 22

The Chicago Police Riot

The Democratic National Convention became a disgraceful battleground between anti-war protesters and overzealous law officers

John Dupree always liked to say that Eleanor Guilfoyle was the prettiest girl in Canaryville, at least until Marge Fitzpatrick moved into the neighborhood.

John and Sis, the nickname which Eleanor went by, grew up four houses apart on South Throop Street on the south side of Chicago, hard by the Union Stock Yards where both their fathers walked to work each day — Patrick Guilfoyle as a butcher, and Edward Dupree as a freight handler for one of the railroad companies that shipped the cattle in for slaughter.

Sis was the eighth of 11 staunchly Irish-Catholic Guilfoyle children, John was the third of four equally staunchly Irish-Catholic Dupree kids. John was two years older than Sis, but there was always something that drew the two of them together, and usually when John would go to the Guilfoyle house, it was to spend time with Sis, under the guise of wanting to meet up with her brother, Lloyd.

Lloyd figured this out sometime around freshman year in high school and he never really had a problem with it. In fact, he often told John that when Sis reached high school age — not a god-damned day before — he wouldn’t play the protective big brother card if John ever wanted to ask Sis out to a dance or a Charlie Chaplin movie. But it was never that way for John. Sis was his best friend, and that’s always how he and she wanted it.

And so it was that Sis did what any best friend would do when Marge Fitzpatrick’s family moved into Mrs. Mulberry’s house across the street from the Guilfoyle’s, and Sis saw the look in John’s eyes the first time he met the new neighbor. She made the introduction and helped facilitate a union that was still going strong some 48 years later.

John and Marge officially became a couple when John was a senior, and the moment Marge graduated St. Mary’s in 1923, she took his hand in marriage and the newlyweds moved into a bungalow a few blocks away from where their families lived right there in Canaryville. They were South side through and through. Within a year, they were the parents of a beautiful green-eyed, dark-haired bundle of joy whom they named Olivia Grace.

The young family went through some tough times, especially with Marge unable to work as she cared for the baby. John toiled days at the Martin Senour Co. paint factory to pay the bills as well as the cost of evening classes at Northwestern, where his goal was to earn a degree in political science which he hoped would help him gain entry into the law program at DePaul.

Along the way, John befriended a charismatic and energetic fella named Richard Daley, at once an aspiring law student at DePaul who had begun to dip his toes in the roiling waters of Chicago politics while earning a wage to defray his tuition by working in the rough-and-tumble meatpacking district pushing cattle through the stock yard pens, as well as serving as the manager at the Hamburg Athletic Club.

Daley spent some of the scant free time he had perched next to John on bar stools at South side joints that generally ignored Prohibition like the The Pump on Halstead Street, or Babe Connelly’s Bar on 37th Street, tipping a few cold beers and solving the country’s problems.

The topics of discussion were wildly diverse, ranging from the cases they were studying in law school, to the turbulent political climate in Chicago, to the blood on the hands of Chicago crime boss Al Capone, to whether their beloved White Sox would ever recover from the devastating Black Sox World Series scandal of 1919. They were men of similar upbringings and religious beliefs, men of education, men of ambition, and they had well-formulated designs on how they were going to make their city better — John becoming an attorney who would represent the poor and disenfranchised, Richard fixated on a career in government.

One of their mutual friends happened to be Lloyd Guilfoyle, Sis’ brother, who occasionally played softball with them, or joined them for poker games at the Hamburg AC. One summer night in 1930, Sis — who by then was working as a secretary at the same paint factory where John was employed — took John up on his request to come watch he and Lloyd play ball at Mark White Square Park.

Little did John know that that invitation would be the impetus for changing the course of Sis’ life, just as Sis’ introduction of John to Marge when they were kids changed his life. After the last out was recorded, Sis left the bleachers and came down to the field to hug both John and Lloyd, and they introduced her to the team’s second baseman, Richard. The rest, as they say, is history.

A few weeks later Richard took Sis to a White Sox game for their first date. Six years hence, in June of 1936 — just months before Richard was elected to the Illinois House of Representatives, kicking off one of the most iconic political careers in United States history — they were married at St. Bridget’s. Among the guests were John, Marge, and 11-year-old Olivia, who in the coming years would occasionally babysit the first three of the Daley’s seven children who were born before she left Chicago to attend Fordham University in New York, which led to her meeting her future husband, Jack McDonald.

Before he even started studying law, Daley was already a Democratic party precinct captain by the age of 21, worked in the City Council office as a clerk, and served as a ward committeeman. By the time he entered DePaul he was reasonably certain that he’d never practice, but he went ahead and obtained his degree, married Sis, and promptly won election to the House. In 1938 he ascended to the state senate, served six years as the Senate minority leader, and during that time was also Illinois Governor Adlai Stevenson’s state director of revenue. In 1950 he was elected Cook County clerk, and in 1953 became the chairman of the Cook County Democratic Party, paving the way for his successful run for mayor of Chicago in 1955. He ousted incumbent Mayor Martin Kennelly in a bitterly contested primary, then defeated Republican Robert Merriam in the general election.

Daley was surrounded by a phalanx of sharp-minded advisors and yes men, but when he really needed an intelligent and unbiased ear, especially when he reached City Hall and took a stranglehold of the Chicago political machine, he usually turned to his good friend, John Dupree. And rarely did the two men speak more in a single given year than 1968 when Chicago erupted in a volcano of violence as its streets became a battleground between anti-war protesters and a Chicago police force that was on high alert, by the mayor’s order, to quell any threats of disruption to the Democratic National Convention by whatever force was necessary.

To have the convention in Chicago was like a lifetime achievement award for the 66-year-old Daley, a glad-handed pat on the back for all the work he had done for the party at the local, state, and national level. The last time it was held in Chicago in 1956, he had just begun his first term as mayor. Now, he was a larger than life figure in the city, and he considered being the host mayor for the convention as one of his crowning glories. Instead, it became a blight on his decorated resume and the fallout resulted in irreparable damage to his legacy.

The seeds for trouble began germinating early in the year because of what was happening in Vietnam. Fueled by the Tet Offensive, Walter Cronkite’s pronouncement that the war was no longer winnable, and the grisly nightly television images emanating from those jungles, Vietnam was tearing the nation apart, and the Democratic president — who it was quite naturally assumed would be coming to Chicago seeking a second term in the White House — was in the eye of the storm.

As early as March, peace activist groups and anti-war factions including the National Mobilization Committee to End War in Vietnam (MOBE), Students for a Democratic Society (SDS), and the Youth International Party (Yippies), were planning protest marches in Chicago during the late August convention to rail against President Johnson’s handling of the war. And even after Johnson stunned the nation with his announcement that he wouldn’t be accepting the party’s nomination, the protesters were undeterred because Johnson’s vice-president, Hubert Humphrey, was the leading candidate to head the ticket, and he was in favor of Johnson’s policies regarding the war.

Daley’s response to the planned infiltration was to refuse to grant permits which would allow the demonstrators to protest legally. “No thousands will come to our city and take over our streets, our city, our convention,” Daley said with typical bravado and defiance.

Barely days after that statement, Daley exacerbated the situation in the wake of the assassination of Dr. Martin Luther King, Jr. Race riots broke out in the hours after the tragedy, and on the West side, 11 blacks died and 20 blocks went up in flames with more than 120 fires damaging 210 buildings to the tune of approximately $10 million. Daley had to call President Johnson to request 5,000 U.S. Army soldiers be flown in from Fort Hood, Texas. to help suppress the rioting, and afterward, the mayor heavily criticized his police superintendent, James B. Conlisk, and the entire department, for what he perceived as it’s too-cautious handling of the incident.

During a press conference at City Hall, Daley said, “I said to (Conlisk) very emphatically and very definitely that an order be issued by him immediately to shoot to kill any arsonist or anyone with a Molotov cocktail in his hand, because they’re potential murderers, and to shoot to maim or cripple anyone looting.” Daley supporters deluged his office with grateful letters, but the press skewered him, and black leaders such as the Rev. Jesse Jackson called it a “fascist’s response.”

The day after the “shoot to kill” proclamation became public knowledge, Daley called John Dupree to gauge his reaction, and John said to him, “Richard, I understand why you said what you said, but I think you may have opened the door for some real trouble when the convention comes here.” John knew the anti-war groups were coming to town, and now that Daley had derided his own police force, it was a recipe for potential disaster with the angry cops hellbent on atoning for their alleged mishandling of the riots. Taking John’s advice, Daley backed away from the statement, saying at a City Council meeting, “It is the established policy of the police department — fully supported by this administration — that only the minimum force necessary be used by policemen in carrying out their duties.” Still, the die had been cast, and the police were not going to make the same mistake when the convention arrived.

By the time the delegates began flooding into his city, the mayor had transformed Chicago into a police state in the hope that the massive show of force would dissuade the dissenters from causing trouble. The area around the convention site — the International Amphitheater on the South side near the Union Stock Yards — was a veritable fortress, protected by more than 5,600 Illinois National Guardsmen, plus every member of the powder-blue shirt and helmeted Chicago police force, nearly 12,000 strong, armed not only with the standard issue firearm and billy club, but with mace, tear gas, and riot gear.

In case that wasn’t enough, there were 5,000 more Guardsmen on stand-by, as well as 7,500 regular army troops at Fort Hood, Fort Sill in Oklahoma, and Fort Carson in Colorado who could be flown in within 24 hours. Further, there were more than 1,000 Secret Service agents, military intelligence officials, federal narcotics investigators, and FBI agents roaming the city with their ears to the ground snuffing out potential uprisings and conflicts.

None of which deterred Olivia in her eagerness to get to Chicago. Having never attended a convention, she had been looking forward to this all summer, especially since she and her parents would be guests of Daley, the most powerful man in Chicagoland. But as the day of her flight neared, Jack pleaded with her not to go. “Liv, I wish you’d stay home,” Jack had said numerous times as reports of the impending violent dissidence usurped Vietnam in the nightly news A block. “And I don’t think your parents should go into the city, either. Tell them to stay out there in Hinsdale where it’ll be safe.”

Naturally, the staunch Democrat would have none of it. “I’m going, and it’ll be fine,” Olivia said. “This is a big moment for Mr. Daley; I’ve known him almost my whole life, and we owe it to him to be there for support.”

“Bullshit,” Jack said. “Mayor Daley has enough on his mind and he won’t be checking his guest list. He’ll understand if you and your parents sit this one out. His town is ready to explode, and I don’t want you anywhere near it.”

“Jack, I know you don’t care about politics, but this is the World Series to me, the Rose Bowl, or whatever other sports analogy you’d like me to use here. I’ve been looking forward to this all year.”

“Yes, believe it or not I get it, I do. But there’s this really useful invention known as the television, and we happen to have one sitting right there in the living room. Guess what? Everything that happens in Chicago will be shown right there on that tube. And here’s the best part, you won’t be in the middle of a fucking riot!”

Needless to say, Olivia boarded her flight at LaGuardia, after Jack sent her off with a loving, worrisome kiss. Why are the women in my life so headstrong, Jack thought to himself before saying, “Be careful.”

“I will.”

By the time Olivia landed at O’Hare on Sunday afternoon, it had become clear that Chicago was on the verge of boiling into a sea of civil unrest. On Thursday, Aug. 22, four days before the official start of the convention, a 17-year-old Sioux Indian from South Dakota was shot dead by police who said he pulled a gun. The next day, the Yippies gathered en masse at the Civic Center plaza in the Loop where they nominated their own presidential candidate, Pigasus the pig. The pig and seven of the Yippies were arrested. And so it began.

The convention was formally opened by Daley on Monday night, Aug. 26, and Daley reiterated, “As long as I am mayor of this city, there’s going to be law and order in Chicago.” There was plenty of law, and absolutely no order over the next four bloody days that reinforced microcosmically how divided a nation the United States was.

Thousands of protesters gathered each night in Lincoln Park and Grant Park, whipped into a frenzy by leaders of the Yippies, MOBE, SDS, Black Panthers, and other satellite radicals such as Allan Ginsberg, Norman Mailer, David Dellinger, William Burroughs, Tom Hayden, Rennie Davis, John Froines, Lee Weiner, Abbie Hoffman, Bobby Seale, Phil Ochs, Jerry Rubin, and Dick Gregory, preaching their New Left politics with street theater tactics. Several marches toward the Amphitheater were attempted, but all were beaten back by the mace-spraying, tear gas-throwing, club-swinging police force, and hundreds were injured and/or arrested. Night after night the protesters refueled with fury and vitriol and pressed on despite the heavy-handed opposition, and with network television cameras broadcasting the uprisings nationwide, Americans grew even more despondent about the unraveling of society.

Never was this more apparent than the evening of Aug. 28 when the violence escalated nearly out of control. Approximately 10,000 gathered at the Grant Park band shell for MOBE’s anti-war rally, surrounded on all sides by the police, with National Guardsmen perched on the roof of the Field Museum with rifles at the ready. As the rally came to an end, a young man began to lower the American flag near the band shell. Police rushed in to arrest him, and then several others completed the flag lowering and attached a blood-spattered shirt to be raised in its place. Police moved in again and a battle ensued, during which Rennie Davis of MOBE, whose father had been former President Harry S. Truman’s chief of staff on the Council of Economic Advisers, was beaten unconscious.

David Dellinger, one of America’s foremost radicals who in 1943 was arrested for failing to report for his World War II draft physical, took control at this point and instructed a march to the Amphitheater. Because they didn’t have a permit, the police refused to allow them to move on the sidewalks, and the march stagnated. After an hour of heated and fruitless negotiation, the protesters tried to cross over to Michigan Avenue, but both the Balbo and Congress bridges were blocked by Guardsmen armed with machine guns.

The mob moved north and was able to surge onto Michigan via the unguarded Jackson Street bridge, and then headed back south on Michigan toward the Hilton Hotel where many of the delegates, and most of the media, were headquartered. With cameras rolling, the police forcibly halted the march, and the melee became the signature event of the week, the Battle of Michigan Avenue as it was dubbed. As the police clubbed, the protesters fired back with fists and rocks and whatever else they could find to throw. Many were heard to be chanting, “The whole world is watching!” and they were right. “The conduct of the authorities here resembles the conduct of the Russians toward Czechoslovakia,” said the poet, Ginsberg.

Meanwhile, inside the Amphitheater, tensions were equally stretched to the limit as the Democratic Party came unglued over its internal disagreement on Vietnam. Having defeated the Germans and Japanese in World War II, it quickly became apparent that the rising Soviet Union, and the potential spread of its Communist government, would be America’s new primary enemy. Stopping the threat of Communism became paramount, and the United States decreed that it would intervene in the affairs of countries it deemed susceptible to that influence. It was this policy that drew America into the Vietnam conflict in an effort to keep South Vietnam from being overrun by Communist North Vietnam. The Democrats could not come to a unified consensus on Vietnam, with Hubert Humphrey upholding President Johnson’s handling of the war, and Eugene McCarthy and George McGovern going the other way and siding with the anti-war faction in the belief that it was time to get out of Southeast Asia.

With nominations underway, Massachusetts Senator Abraham Ribicoff, in his speech promoting McGovern, said, “With George McGovern as President of the United States we wouldn’t have Gestapo tactics in the streets of Chicago.” Mayor Daley, standing in plain sight on the convention floor, angrily shook his fist at Ribicoff and, depending on the account, either called Ribicoff a “fucker” or a “faker.”

With the anti-war delegates getting increasingly agitated by what they were hearing from the stage, the police inside the arena became more and more antagonistic and scuffles broke out, again on national television. In one memorable incident, CBS reporter Dan Rather was knocked to the floor as he tried to interview a delegate who was being forcibly removed from the convention.

Rather was able to recover and he told Walter Cronkite and the viewers, “Walter… we tried to talk to the man and we got violently pushed out of the way. This is the kind of thing that has been going on outside the hall, this is the first time we’ve had it happen inside the hall. I’m sorry to be out of breath, but somebody belted me in the stomach during that. What happened is a Georgia delegate, at least he had a Georgia delegate sign on, was being hauled out of the hall. We tried to talk to him to see why, who he was, what the situation was, and at that instant the security people, well as you can see, put me on the deck. I didn’t do very well.” Cronkite then said, “I think we’ve got a bunch of thugs here, Dan.”

Like most Americans, Jack sat in the living room mesmerized by what was taking place, and he wondered where his wife was, and whether she and her parents were safe. Long after midnight, Jack got his answer, awakened by the phone on the nightstand next to his bed. When he picked up the receiver, he heard Olivia crying on the other end.

“Are you OK?” Jack said, immediately alert despite the hour. “What happened?”

“I’m OK, but we’re not going back downtown tomorrow. It was awful, Jack. I’ve never seen anything like this. We saw on the television monitors what was going on outside the hall, all the rioting and the beating, and then the people on the floor in the building were fighting. You were right, this was a bad idea. I can’t wait to get out of here.”

When Olivia hung up, she sat down at the kitchen table of her parents’ home in the safety of suburbia, and they talked into the early hours of the morning, lamenting the fact that the Democratic Party was irreparably broken, and that there was no way the Republican nominee, Richard Nixon, could lose the election. It was clear the Democrats should have nominated an anti-war liberal, but with only 15 states choosing their delegates by primary, Humphrey was able to secure the vast majority of delegates in the states where they were selected by county committeemen, state party officers, and elected officials. Men like Daley and his minions that kept his political machine humming.

When the convention was closed the following night, Humphrey was officially confirmed, but only the most optimistic members of the party truly believed he stood a chance after what had transpired in Chicago. The final tally was nearly 700 arrests, more than a thousand injuries to police and protesters, several hundred of those serious enough to be treated at area hospitals. And during the week of the convention, it was reported there were 308 American casualties and more than 1,100 injured during fighting in Vietnam.