From off the prairie the man arrived, settling at the bend of the great lake. There along its swampy shores he built himself a cabin. There among the Indians he made his home.

His name was Jean Baptiste Point du Sable. It was only years later—the land no longer a field of wild flowers but a seething metropolis of three million—that historians salvaged his name and declared him Chicago’s first permanent settler. their discovery was heavy in irony. Du Sable was not an expatriate of european descent but a dark-skinned trapper from Haiti. In spite of all the...

The day’s featured speaker, Harold Washington, jumped from foot to foot. Small puffs escaped from his mouth. The wind chill was near 80 below zero on that frigid Sunday in January 1982, yet the radiators weren’t working. Washington, the sort who made little time for things as mundane as adequate clothing, arrived with no hat, no scarf, and no gloves, though forecasters were saying it might rank as the coldest day in Chicago history. Washington shivered on stage as he cursed himself for bothering to show. Silently, he blamed a man named Lu Palmer for his discomfort.

The event was...

In the summer of 1982, two thousand people showed up at a south side church for a daylong event that Lu Palmer had billed as a “black plebiscite.” the idea was to invite anyone who was anyone in black movement politics and, at this gathering of the clan, crown Harold Washington as their choice for mayor. Speaker after speaker cited informal polls that showed Washington far more popular than Palmer, Jesse Jackson, and other well-known black local figures. Near day’s end, a vote was taken: Washington outdistanced the second-place finisher by something like five-to-one. All that remained was the formality...

Early in her tenure as mayor, Jane Byrne would regularly invite Renault Robinson to her office to talk politics. Shortly after taking office, Byrne named Robinson to the Chicago Housing Authority (CHA) board, a selection so controversial that, though Byrne appointed her brother’s brother-in-law to another post that same day, it was Robinson who made headlines. The machine regulars were nearly apoplectic at the thought of lending support to this rapscallion whose racial discrimination suit against the city established hiring and promotion quotas inside the police department.

Robinson’s role as a trusted Byrne adviser would last perhaps a year. Later...

Two emissaries representing Harold Washington were ushered into Jesse Jackson’s living room on Chicago’s south side. There, Jackson’s icy reception confirmed what they already knew. years later Renault Robinson spoke with pride of his intimate sessions with Washington during those months when electing a black mayor in Chicago seemed far-fetched. yet tarnishing his memories were assignments like this one, an interminable visit that lasted well past midnight on a hot summer night in August 1982.

Under the best of circumstances, it is not easy to deal with Jesse Louis Jackson, a man alternately capable of nobility and of peevishness. And...

Reporters working out of the City Hall press room were skeptical. To them, several hundred angry people protesting Jane Byrne’s appointments to the Chicago Housing Authority was something that made their jobs more interesting for a few days but nothing more. It hardly proved that black Chicago was on the verge of a political miracle. Harry golden Jr., the City Hall reporter for theSun-Timesstretching back to the 1960s, didn’t look upon the Chicago Fest boycott as significant so much as ironic. White teens showed up wearing t-shirts thanking Jesse Jackson for convincing black people to stay away from...

Never had the antimachine movement seemed so ripe with possibilities. Unity, the machine’s great strength throughout Richard J. Daley’s twenty-one-year tenure, was nonexistent and potentially a fatal weakness. To no one’s surprise, in December, with the primary two months away, the Democratic Party endorsed Byrne for mayor. Yet the party’s endorsement no longer meant the full weight of fifty ward organizations around the city, black and white. Only eleven of the city’s twenty strongest ward operations were with Byrne; the other nine were with Daley.

Against this backdrop, an energetic antimachine movement was assembling, led by a black candidate who...

Late in December, with the primary election less than two months off, Jane Byrne dumped one of the two white women she had named to the public housing board that past summer and replaced her with someone black. The party’s polls showed that, among whites, Byrne was ahead of Daley. It was time to tend to the black vote.

Byrne strategists all but conceded that Washington would win among black voters—if not a majority, then at least a plurality. “Whoever wins the primary had to come in second” among blacks, said Byrne campaign manager William griffin. After all three...

Harold Washington could have used the city’s segregation to his advantage when he delivered a speech making his case why black Chicago should vote for him. Instead, he instructed aides to promote his talk as a major address. His choice of venues was equally defiant. He gave his talk at the Bethel AME (African Methodist episcopal) Church on the south side. Bethel was Lu Palmer’s turf. It was where Palmer held the 1982 plebiscite that crowned Washington the movement’s choice for mayor; it was where Palmer and his cohorts gathered for countless mass meetings.

Washington started off not so much...

Washington’s victory got prominent play on the networks. All three big morning news shows broadcast time and again a snippet of Washington surrounded by a crush of people, announcing hoarsely that he “proudly and humbly” accepted the Democratic nomination for mayor. He appeared live on theTodayshow, and his picture graced the front page of theNew York Times. The sixty-year-old son of a precinct captain, theTimesreported, beat the fabled Chicago political machine.

Washington was groggy the next day when he began meeting with his strategy team. With the general election only seven weeks away, there was...

Leanita McClain walked into theTribunethe morning after Washington’s primary victory expecting a noisy newsroom alive with talk. She looked forward to teasing the colleagues with whom she had been jousting for weeks—colleagues who couldn’t imagine that Washington might win. If nothing else, McClain, the first black to sit on the paper’s editorial board, expected congratulations. The one thing she didn’t figure on was the silence that would begin seven of the more agonizing weeks of her life.

The cliché about Chicago was true: Its citizens follow local politics with the same fervor they do the Cubs and...

“Fast Eddie”—that’s what the columnists and pundits had been calling Ed Vrdolyak for as long as anyone can remember. Certainly Vrdolyak wasn’t wasting any time organizing against Washington. At an informal City Council meeting held the Friday after the general election, Vrdolyak stood to warn his council colleagues. Already a Washington aide named Jim Houlihan, he said, has started telling people the mayor-elect would work to replace any alderman who didn’t swear his allegiance to his administration. Northwest side alderman Richard Mell stood to confirm the threat. Later, Houlihan told a reporter that he said nothing of the sort...

The night after the big council meeting, the telephone rang late at the Vrdolyak home. “Well, Alderman, did you have a good time today?” It was Washington. He extended an invitation to talk. “You and me have to shoot some pool,” Washington said. Prior to 1983, the two would occasionally get together. Every so often Vrdolyak would stop by Washington’s congressional office on a Saturday, postgolf, dressed in a polo shirt, and the two would talk politics for an hour or so. Now it was time to talk, adversary to adversary.

The two met the next day, Tuesday, in Washington’s...

Ed Burke, more than Ed Vrdolyak, fought Washington on the front lines of Council Wars. Burke was the one on TV decrying the mayor’s latest proposal or cynically casting the mayor as nothing but another politician out for himself and his cronies.

Burke, like Washington, had been born into the machine. Unlike Washington, though, he was born to a nobleman, not a serf. Burke’s father Joe ran the Fourteenth Ward for well over a decade, serving as both alderman and committeeman of his southwest side fiefdom. Burke was still a teen when he met a senator named John Kennedy. In...

Harold Washington didn’t take it well the time Ed Vrdolyak fluttered his arms and sang out “pretty please” in falsetto. “You’re about to get a mouthful of something you don’t want, mister,” he said, pointing his gavel at Vrdolyak. Ed Burke jumped out of his seat: “Is that a threat? If it is, come on down here on the floor.”

Threatening to punch a rival in the mouth wasn’t something he needed, but Washington made matters worse by responding to Burke. “No,” he said. “You come up here. You come up here.” Alderman Wallace Davis, a Washington ally, leaned over...

Nate Clay read with bemusement the many articles picking apart Jesse Jackson’s motives in running for president in 1984. None got it right, at least in the eyes of this man who had worked with Jackson on and off for years. What made Jesse run? First you need to understand Alexander the great, according to Clay. Alexander, it was said, “after conquering the world sat down and cried because there was nothing else to conquer.”

“With Harold’s election, Jesse was no longer the black community’s top figure,” Clay said. He had no mayor to rail against; he had no local...

Everything was going well for the twenty-nine, mainly because things were going so poorly for Harold Washington. As the midpoint in his term approached, the prevailing image of Washington was that of a terribly outmatched bumbler up against craftier opponents. One political writer likened him to Jimmy Carter, sincere but inept, a good-hearted man unable to find the levers of power to actually accomplish anything. Washington could rant about the underhanded methods of his foes. But that seemed to only further ingrain the image of an oversized Vrdolyak manhandling a child-sized Washington, as if Vrdolyak were able to lean a...

And like that, the momentum shifted again. Late in 1985, the city learned that several black aldermen and a Washington appointee were videotaped accepting money from an FBI informant who was posing as a businessman. At the center of the sting was Clarence McClain. With Washington’s bid for reelection barely a year away, McClain, the official whom Washington had banned from government after it was discovered that he was convicted on a pimping charge in 1967, was again dominating the news.

The years following his expulsion from City Hall were not good ones for Mc-Clain. He remained on Washington’s political...

Chicago was a city that so emphatically defined itself in black and white that it seemed absurd that its Latino population could dominate local politics as they did for a brief moment in early 1986. Before there was Council Wars, a suit had been filed in federal court charging that the city’s ward map discriminated against black and Latino voters. A judge agreed the map was discriminatory and ordered that special elections be held in seven of the city’s fifty wards. All seven were represented by allies of Vrdolyak. And like that it was possible that the council standoff might...

There may have been a time when Jane Byrne was considering a life beyond politics. The gossip columnists had her weighing offers as a television analyst, a college instructor, and a consultant. She sang a line in aUSA Todaycommercial; she lent her image to a chain of Mexican restaurants. But a small squib announcing that Byrne was studying Spanish was one of many clues that revealed what the former mayor really had on her mind. By mid-1985, with election day nearly two years off, she had hired a press secretary. In July of that year, she declared her...

Long after it was too late, long after the bad press and the grumbling even among loyal partisans, Harold Washington would admit that Renault Robinson was a poor choice to head the Chicago Housing Authority. Washington’s confession came in the final months of his first term, while overseas and drinking in the company of several aides late one night.

I know he’s not working out, Washington said. But look at Robinson’s life. Washington was twenty years Robinson’s senior, but he confessed to feeling inspired by this young cop who took on the top brass over the issue of police brutality,...

Harold Washington died at his desk the day before thanksgiving. He was talking with his press secretary, Alton Miller, when Miller, glancing at his notes, heard a “rattling, raspy sound”—the kind of crude noise, he would later say, that a man makes outdoors when collecting his phlegm to expel a big gob of spit. He looked up. Washington was leaning forward, his cheek pressed against the desk. Miller thought he was bending over to pick up something from the floor, but then he realized Washington wasn’t moving.

Miller jumped from his chair. Washington’s bodyguards and then the paramedics worked...