Bill Daley with Reverend Marshall Hatch and members of the MAAFA Redemption Project at New Mount Pilgrim Missionary Baptist Church in West Garfield Park Credit: Chris Costoso

The year 2018 was considered by many pundits the year of the woman. From congressional bids to local and state races across the country, women challenged and in many places won power at rates previously unseen in American life. But just when momentum seems to be building in national politics, Chicago seems poised for an abrupt turn back toward the masculine in our mayoral election. While headlines early in the mayoral race focused on the celebrity and youth support behind Amara Enyia or the supposed front-runner status of Cook County Board president Toni Preckwinkle, it seems that in truth Chicago may be on the brink of the reign of yet another Daley.

Bill Daley, the youngest child of Mayor Richard J. “Boss” Daley (1955-1976) and the younger brother of Mayor Richard M. Daley (1989-2011), now seems to be the surest bet to make an inevitable runoff election in a field rocked by the scandal of long-standing City Council boss Ed Burke, alderman of the 14th Ward. Candidates who’ve operated in local and state politics for years such as Preckwinkle, Susana Mendoza, and Gery Chico have been weakened by their personal and professional ties to Burke.

Meanwhile, the 70-year-old Daley has quietly emerged as a potential front-runner with little of the stink of Burke and Chicago machine politics on him. Despite Burke’s famous fealty to the two previous Daley mayors, Bill has escaped much of the scrutiny of other candidates because much of his political career has happened in D.C. under Clinton and Obama rather than in his ancestral Bridgeport haunts. It seems possible, although perhaps shocking, that in a race where much of the conversation has been focused on women-of-color candidates like Enyia, Preckwinkle, Mendoza, and Lori Lightfoot, a white guy from the most famous Democratic political family this side of Camelot might be poised to step into the big seat on the fifth floor.

Daley, to be sure, seems to be the smoothest operator of his family, less prone to verbal gaffes than his father or brother. If anything, he seems to aggressively avoid making much of an impression at all. While other candidates have busied themselves with ballot challenges or scandal management, Daley has been content to amass a war chest that is by far the largest in the field ($5.94 million compared to the next closest, Toni Preckwinkle’s, at $3.75 million). Daley’s list of donors at $25,000 and up reads as a who’s who of Chicago business and private equity types, including Pritzker matriarch Marian (married to Jay) and Cubs CEO Tom Ricketts. Ironically, Daley has turned his lack of local political bona fides into an advantage of sorts. He avoids the more extensive political connections to Burke of other front-runners while being able to count on the endorsements of famous national politicos like Al Gore.

Gore’s endorsement of Daley would seem a surprise to some. Gore championed Daley’s ability and willingness to be an advocate for environmentalism, while Daley simultaneously received endorsements from the plumbers’ union that was essential in keeping lead service lines in use for years in Chicago after the potential health risks were well-known. Daley may also stand to benefit from his association with Obama. Though the former president is unlikely to endorse him personally, it wouldn’t be shocking if Obama were quietly rooting for Daley given the candidate’s stated opposition to a community benefits agreement for the forthcoming Obama Presidential Center.

Now Daley is positioning himself toward a strong base that includes a good bit of Chicago’s business community, some elements of organized labor, and fans of past presidents he’s served under. Daley’s overtures toward Obama’s base have been met with a mix of confusion and hostility, but may prove persuasive to fans of the former president who don’t remember the unseemlier dimensions of past Daleys. Bill has suggested the Dan Ryan Expressway name be changed to honor Obama and garnered the endorsement of his brother’s former mayoral challenger, Bobby Rush. These machinations seem designed to portray him as the kindler, gentler Daley, eager to sell out a former close family ally (Dan Ryan was the Cook County Board president considered the second-most powerful Democrat next to Richard J. Daley) and to show that Bill will be more attentive to the needs of black voters than his predecessors.

Bill, for his part, seems to be in lockstep with his family’s traditions of solidifying and expanding executive control in Chicago, as evidenced by his opposition to an elected school board and his proposal to merge Chicago Public Schools and the City Colleges. Richard M. famously unilaterally closed Meigs Field and reconstituted the leadership of CPS into its current structure. The elder Daley exercised wide-ranging political control across the city’s Democratic machine and strengthened the notorious patronage system that would produce politicians like Burke. In a muddied field it seems likely that the city of Chicago could experience another generation of Daley power consolidation.

This Daley, at the very least, seems unlikely to match his father or brother’s two-decade rules of the city. He could, though, find himself in the most difficult fiscal and political situation of the bunch. He would assume control of a city that is losing population (and in particular hemorrhaging black residents), with an embarrassingly low homicide clearance rate, historically strained community-police tensions, and a continually darkening financial picture. The next mayor will be tasked with addressing all of these issues with a City Council still reeling from the made-for-TV defection of Danny Solis in aid of federal investigators.

Will the next mayor be a Daley? The political planets are aligning to make Bill Daley a major player in Chicago. Black and Latinx communities figure to have their support fractured across a number of candidates, perhaps opening the door for a “trusted” candidate like him to peel off support. Daley may have as good a shot as any at making the likely runoff and perhaps winning the whole thing. If he does make the runoff, it seems likely that a rush of cash would flow into his already bloated war chest. His family’s old power base of working-class white voters would likely fall in line. Those voters, coupled with even modest support from communities of color, would place him in a strong position to win it all, particularly with the diminished voting power of black Chicago due to out-migration. Many younger voters, either new to the city or new to civic life, may not remember the Daley family’s former misdeeds and penchant for power grabbing, and may be seduced by the chance to have a former Obama staffer in City Hall. Only time will tell if he’ll continue his habit of following Rahm Emanuel—whom he replaced as White House chief of staff after Emanuel resigned to run for mayor—into a new job.   v