The next morning the Tribune lauded Washington as “a symbol of success and dreams realized for people who felt they had little reason to dream, let alone achieve,” while again noting that “his tangible record of accomplishments is a short list.” Economic development commissioner Rob Mier would write that “many of his goals and plans remained unfulfilled or barely started.” Mier also recognized that Chicago’s loss was greater because Washington had “died at the peak of his power.”
Tribune reporter John Kass highlighted how Washington had been “an incredibly charismatic leader,” but one of Washington’s most fervent early backers identified the mayor’s greatest mistake. “He took the power to himself, almost like Mayor Daley” in earlier decades, “and the political maturity of black politics stopped while he increased his power.” White 49th Ward reform alderman David Orr, who became interim mayor upon Washington’s death, had articulated the underlying problem months earlier: “There’s a large group of black aldermen … who don’t support reform but who have to vote with the mayor because he’s so popular in their wards.” By tolerating rather than purging those black aldermen who professed to support him while nonetheless remaining fully loyal to the Democratic party machine, Washington had advanced “his own political self-interest at the expense of institutionalizing his reform movement,” wrote historian Bill Grimshaw, the husband of Washington’s top political aide, Jacky Grimshaw.
The enormity of Washington’s failure became clear within the first hours after his death, as his city council majority sundered into two angrily hostile camps. Washington’s true supporters rallied behind the mayor’s council leader, 4th Ward alderman Tim Evans, with whom Barack and DCP’s Altgeld asbestos protesters had met eighteen months earlier. Washington’s opponents eagerly reached out to the black machine aldermen, who now controlled the balance of power in a political world where they no longer had to bow to a singularly charismatic leader. Washington’s political base “unraveled immediately after he was pronounced dead,” John Kass wrote, and Rob Mier also rued “the immediate collapse of his political coalition.”
Over the Thanksgiving holiday weekend, the two factions warred publicly as Washington’s body lay in state for a fifty-six-hour around-the-clock wake in the lobby of City Hall. Monday night at the UICC Pavilion where Washington had hosted his Education Summit just seven weeks earlier, his official memorial service turned into a political rally for Evans. Yet the only votes that would count were those of the fifty city council members, and by Tuesday morning, there was little question that 6th Ward black machine alderman Eugene Sawyer would become Chicago’s next mayor thanks to Washington’s hard-core opponents plus at least five black aldermen who would support Sawyer over Evans.
As Tuesday night’s council meeting convened, a crowd of thousands stood outside City Hall, chanting “No deals” and “We want Evans.” Clownish behavior marred the council’s proceedings as protesters mocked black Sawyer allies like 9th Ward alderman Robert Shaw, and Sawyer was not formally elected as Harold Washington’s successor and sworn into office until 4:00 A.M. Wednesday.
In skin color Gene Sawyer was just as black as Harold Washington, but as the angry crowd well knew, Chicago now had a completely different mayor than the one it had just buried. When Sawyer was asked by a historian some months later about Washington nemesis Ed Vrdolyak, his answer highlighted the chasm: “He’s a fun guy!”64
“I loved Harold Washington,” Barack blurted out years later when asked what he had thought of the mayor. He once wrongly but perhaps wishfully stated that in 1985 “I came because of Harold Washington,” and at another time, he mused that “part of the reason, I think, I had been attracted to Chicago was reading about Harold Washington.” There was no doubt that Washington, or more precisely Washington’s treatment at the hands of the Vrdolyak majority during Barack’s first nine months in Chicago, contributed in some degree to Barack’s own embrace of a resolutely black racial identity. “Every single day it was about race. I mean every day it was black folks and white folks going at each other. Every day, in the newspapers, on TV, in meetings. You couldn’t get away from it,” Obama later recounted. “It was impossible for Harold to do anything.”
Upon his arrival in Chicago, and throughout all of his Oxy and Columbia years prior to Jesse Jackson’s 1984 presidential run, Barack had been “skeptical of electoral politics as a strategy for social change,” he later acknowledged. “I was pretty skeptical about politics. I always thought that the compromises involved in politics probably didn’t suit me.” Jerry Kellman, Greg Galluzzo, and the Alinsky tradition of organizing certainly did not teach respect or admiration for elected officials. But watching Washington week after week, even if he had never been physically closer than in that nondescript Roseland storefront eight months earlier, had fundamentally changed Barack’s mind. “You just had this sense that his ability to move people and set an agenda was always going to be superior to anything I could organize at a local level,” Obama explained in 2011.
In his own telling years later, Obama was in that angry, chanting crowd outside the city council chambers that Tuesday night, witnessing what he called Washington’s “second death.” Yet even at the time he wrote that, Barack understood Washington’s fundamental error, just as Bill Grimshaw had explained it. “Washington was the best of the classic politicians,” Obama told an interviewer. “But he, like all politicians, was primarily interested in maintaining his power and working the levers of power. He was a classic charismatic leader, and when he died, all of that dissipated. This potentially powerful collective spirit that went into supporting him was never translated into clear principles, or into an articulable agenda for community change,” Obama rightly stated in words that would echo painfully two decades later. “All that power dissipated.”
Yet in those last weeks of 1987, Washington’s death strengthened Barack’s belief that now was the time to leave DCP for law school. He had “a sense that the city was going to be going through a transition, that the kinds of organizing work that I was doing wasn’t going to be the focal point of people’s attention because there were all these transitions and struggles and tumult that was going on in the African American community,” he recalled in 2001. “So I decided it was a good time for me to pull back” and attend law school.
Barack’s long-pondered personal essay was finished, but completing his application required soliciting letters of recommendation as well. Al Raby was a recognizable name to anyone who knew the history of the 1960s, and Michael Baron had given him an A for his senior year paper at Columbia, the most serious piece of coursework Barack had ever tackled. Now working at SONY, Baron readily agreed to write a letter. But Baron’s knowledge of him was now more than four years dated, so Barack also went to see John McKnight, asking him to keep their conversation confidential, especially from Greg and Mary. “Would you write me a letter of reference? You’re the only professor I know.” McKnight immediately said yes, but asked Barack what his plans were. “I want to go into public life. I think I can see what can be done at the neighborhood level, but it’s not enough change for me. I want to see what would happen in public life” and “I think I have to go to law school to do that.” McKnight questioned whether Barack understood how fundamentally different life as an elected official would be from that of an organizer. While the latter was quintessentially an advocate, “my experience is that legislators are compromisers,” McKnight observed, people who synthesize conflicting interests. “You want to go into a world of compromise?” he asked. Barack responded affirmatively, saying, “That’s why I want to go into public life” and to pursue a role quite opposite that of a confrontational Alinsky organizer. “It’s clear to him he’s making a decision that that’s not the way he’s going,” McKnight remembered. “He left for a different mode of seeking change.”65
With Gene Sawyer uncomfortably ensconced in City Hall, the Parent Community Council’s ten public forums were surrounded by uncertainty. At the first one, Chicago United’s Patrick Keleher reiterated the business community’s demand for dramatic reforms, and at the third Sawyer pledged “my commitment to the Washington reform agenda.” In response, Manford Byrd protested that CPS’s “many needy students” meant that any improvement