Jasmine Mithani

Chicago’s political history sometimes reads more like a House of Cards script than it does a civics lesson. Terms like “Chicago-style” politics and “the machine” have become ubiquitous nationwide to evoke corruption, quid-pro-quo arrangements, and nepotism. Of course “the machine” is not actually a machine—it is a shorthand for the relationships and strictly enforced loyalties that allowed the Democratic Party to consolidate power in Chicago over the course of the twentieth century. While the machine enjoyed its heyday under the father-son duo of Mayors Richard J. and Richard M. Daley, many of today’s elected officials remain beholden to this power structure or employ its tactics: rewarding supporters with contracts and city jobs, intimidating dissenters, and backing legislation which will line their own pockets.

In our Elections Issue, we assembled a map of mayoral candidates who are implicated in Chicago’s machine through their relationships with the Democratic Party’s head honchos. This week, we bring you Part II, shedding light on a few South Side aldermanic incumbents with strong ties to those same machine operators.



He’s the longest-serving House Speaker of any state legislature in the country, but that lofty distinction doesn’t even begin to adequately describe the reaches of Mike Madigan’s influence. He has garnered a wide reputation as a hard-nosed partisan whose shrewd maneuvers and bottomless financial warchests allow him to wield influence in just about every election or legislative battle in Illinois. He is the chairman of the Illinois Democratic Party, he goes way back with the Daleys, and has donated money to Alderman Ed Burke.

One of his more “notable” legacies? The gerrymandered electoral map that now governs the state, all but guaranteeing Madigan’s re-election as speaker into perpetuity unless newly elected Governor Pritzker makes good on his pledge to establish an independent redistricting commission after the 2020 census.


In her run for mayor, Preckwinkle is positioning herself as an independent figure, pointing to her time as a dissenting voice on city council during the Daley years. Still, Preckwinkle has increasingly become a power player in Chicago politics, and in 2018 she succeeded Joe Berrios as the president of the Cook County Democratic Party, which has historically been the core engine in the Democratic Machine. She has close ties to the Burke family and stood behind Berrios, the disgraced former Cook County Assessor, even after a series of Tribune and ProPublica investigations exposed his office’s corrupt and discriminatory practices. With all of these factors combined, it is arguable that Preckwinkle has become a machine figure in her own right.


Many argue that Mayor Emanuel represents a break from the old machine politics, or at least a very different iteration thereof. Emanuel’s power stems from a different set of relationships: with the Obamas and downtown finance types rather than old political families. Still, there’s no question that Emanuel presides over a power structure which rewards obedience, as evidenced by city council’s tendency to cheerfully “rubber stamp” the mayor’s legislative agenda. And like the bossmen of old, Rahm has a habit of brokering deals that wind up benefiting his pals. (The Lincoln Yards development, for example, was initially supposed to include an entertainment district run by Live Nation, whose board includes Emanuel’s brother Ari.)


The elder Daley was the city’s second-longest-serving mayor. He didn’t invent machine politics but he may have perfected the art, building an efficient political organization through patronage—trading government jobs and services for votes and campaign cash. Although he died in 1976, Daley Sr. left behind a strong culture of pay-to-play that lives on.


As the son of the original bossman, Daley Jr. was bound to follow in his father’s footsteps. During his tenure as mayor, Richard M. Daley surrounded himself with a small circle of fierce supporters whose political future was entangled with his own, bartered with administration jobs, and cemented unwavering support from deep-pocketed developers by exchanging splashy downtown projects for campaign contributions.


Burke more or less inherited his place at the helm of the 14th Ward from his father Joe Burke and is the only sitting alderman who was around during the tenure of Daley number one. He remained an ally to the family throughout both Daley administrations, and was among the coalition of white aldermen who organized to strip power from Chicago’s first Black mayor, Harold Washington, during the “Council Wars” in the 1980s. As a tax appeal lawyer, he’s benefitted from the county’s unfair property tax system (overseen most recently by Joe Berrios) and has stirred controversy in recent years by helping the Trump Tower get out of paying $14 million in taxes. His side hustle has resulted in numerous conflicts of interest; the Better Government Association recently reported that Burke has had to recuse himself from City Council votes 464 times in the last eight years—more than all other aldermen combined. The FBI just booked Burke on federal extortion charges for allegedly shaking down a Burger King franchise.




RAHM: If a City Council seat opens up in the middle of a term—in the case of resignation, death or, in Chicago fashion, corruption charges—the mayor has the power to appoint a replacement. Emanuel appointed Tabares to her current seat as alderman of the 23rd Ward in 2018.

MADIGAN: Her largest campaign donor and political rabbi. Her opponent alleges Rahm appointed her as a favor to Madigan.


RAHM: After taking heat from challengers for accepting sizable donations from Emanuel, Hairston announced she’d donate the money to several community organizations.

BURKE: She has received a handful of donations from each of Burke’s three committees.

PRECKWINKLE: Preckwinkle has been a consistent Hairston supporter, having donated tens of thousands of dollars to Hairston’s fundraising committee.


BURKE: She has received a $500 donation from Burke, which is arguably negligible, especially considering the thousands of dollars he dolls out to other members of city council.


RAHM: Emanuel handpicked King to oversee the highly regarded 4th Ward. Her husband was investigated by the ethics board for lobbying without a permit after he emailed Emanuel’s personal account requesting a fence be removed from a city park to make room for crowds at a house DJ event.

ED BURKE: Despite an awkward dust-up when Burke insinuated his son should date King’s daughter, the two have settled their differences, evidenced by Burke’s small contributions to King’s campaign war chests.

PRECKWINKLE: Like, Hairston, King has a close relationship to Preckwinkle who served as Alderman in this same ward for twenty years. Since stepping down as alderman to run for Cook County Board President, Preckwinkle has carefully shepherded her replacements in behind her: first Will Burns, a former Obama aide whom she’d previously appointed to the state legislature, and then King, for whom Preckwinkle helped secure an Obama endorsement.


RAHM: Sawyer joined Hairston in rejecting Emanuel’s contribution, instead opting to give it to community organizations.

BURKE: Another South Side alderman, another donation…


RICHARD M. DALEY: The mayor appointed her in 2006, kick-starting more than a decade of service in the political sphere.

BURKE: Yet another one of the twenty South Side aldermen to receive a fistful of Burke’s cash.


RAHM: Some Black voters have accused Beale of siding with Rahm in downplaying and covering up the need for reform in the CPD. As a member of the Finance Committee, Beale voted in favor of the McDonald family settlement, which was intended to kept the shooting of Laquan McDonald out of the spotlight. The $20,000 he received from the mayor last year probably doesn’t help his case.

BURKE: Thousands of dollars of Burke donations have fueled his re-election efforts.


RICHARDS J. AND M. DALEY: It really is a whole family business. Thompson is the grandson of Richard J. and nephew of Richard M.

BURKE: A friend of Daley’s is a friend of Burke’s.


RICHARD M. DALEY: Cardenas has served four terms as alderman and is well-known for his ties to the Hispanic Democratic Organization, a historically pro-Daley group, which was ultimately busted for patronage hiring. The HDO helped Cardenas unseat an incumbent to win his first race.

BURKE:  He has received $1,500 from Burke according to the Reporter.


RAHM: Brookins is another recipient of Emanuel’s $20,000 gifts last year.

BURKE: Brookins is the third-largest beneficiary of Burke’s generosity, according to the Chicago Reporter.


RICHARD M. DALEY: Austin was appointed by Daley in 1994, making her one of the more “experienced” members of City Council.

RAHM: Austin has received many thousands of dollars in campaign donations from Emanuel. In October, she was one of a handful of Rahm supporters to receive $20,000 checks from the outgoing mayor.

BURKE: She is one of the twenty South Side aldermen running for re-election who has received financial support from Burke.


MADIGAN: Known to colleagues as “The General” for his legislative maneuvering and political gamesmanship, Quinn’s a carbon copy of Madigan at the city level, a fitting comparison given he runs Madigan’s home ward. The ties are inextricable—Quinn is flush with Madigan money and the two share a local office. Even sexual harassment allegations against Quinn’s brother (a Madigan staffer) couldn’t break up the two.


Carly Graf is a contributing editor for the South Side Weekly. She reported Part I of this piece about the mayoral candidates’ machine ties.

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