A New Yorker's Guide to the Chicago Mayoral Race

A breakdown of the Chicago Mayoral Race through the familiar lens of New York City politics

Over the past week, I have found myself enamored by the Chicago Mayoral Race, largely because it intimately reminds me of countless dynamics present across New York City politics, the helio around which my Substack orbits. 

Inevitably, the political happenings of Chicago and New York are intertwined, with a myriad of parallels and comparisons available between the two. Despite the Windy City (2.7 million people) being roughly one-third the size of Gotham - with only 100K more people than the borough of Brooklyn - Chicago shares a demographic profile closer to New York City than any of the other major cities in the United States.

Like many urban communities across the Northeast and the Midwest, Chicago is experiencing an exodus of Black residents, many of whom are relocating to the South in a demographic shift dubbed the “New Great Migration” - a reversal of migration trends among Black Americans throughout the first half of the twentieth century. This phenomena has significantly altered the character of several historically Black neighborhoods, from Englewood and Austin in Chicago to Bedford-Stuyvesant, Crown Heights, and Harlem. While Asian immigrants have not settled in Chicago at a comparable rate to New York City, the Latino populations of each respective city have grown steadily over the past thirty years, now constituting the second largest demographic group.

With such pronounced demographic shifts, political power becomes more tenuous. 

In both New York and Chicago, “Rainbow Coalitions” that united Blacks, Latinos, and progressive whites - and ultimately delivered Harold Washington and David Dinkins to City Hall, the first Black Mayors in their City’s history - were hailed as the electoral future of the progressive left, capable of transcending both race and class in an era fraught with polarization and tension. However, said coalitions quickly evaporated amidst backlash from white voters, who helped usher in “law and order” Republican Rudy Guliani and the centrist, corporate-friendly administrations of Richard Daley, Rahm Emanuel, and Michael Bloomberg - an era which lasted through the mid-2010’s. 

Local Black political power, which had reached its zenith in the mid-80’s and early 90’s, waned in the wake of Dinkins’ defeat and Washington’s untimely death - ultimately lacking a prominent successor at a time when the Latino electorate, buttressed by a burgeoning populace - particularly Puerto Ricans in New York City and Mexicans in Chicago - became an increasingly viable coalition in Mayoral races, capable of spearheading credible bids for City Hall. Yet, the likes of Fernando Ferrer and Jesus “Chuy” Garcia were never able to best their well-funded opponents, in part because of their pronounced struggles amongst high-income white voters, and their inability to meaningfully coalesce Black voters despite longstanding relationships with area power brokers.

Editor’s Note: If not for the September 11th terrorist attacks, which came on the Tuesday of New York City’s 2001 Democratic Primary, a credible case can be made that Ferrer would have won the Primary - then defeated Bloomberg in the November general, off the strength of the Black and Latino support that was denied to Mark Green. 

Nonetheless, following the unassuming departures of Bill de Blasio and Rahm Emanuel, both cities elected their second Black Mayors - reformer Lori Lightfoot, former chair of the Police Accountability Task Force, and the establishment-aligned, moderate-inclined ex-police officer, Eric Adams - within three years of one another. 

However, Lightfoot’s surprise ascension was due to her anti-corruption bona fides, which saw her main competitors tainted by their connections to the scandal-ridden Alderman Ed Burke, a Daley-era municipal power broker, which helped her score an endorsement from the Chicago Sun Times, making her a favorite amongst high-income liberals adjacent to the Lakefront in the City’s northeast (sound familiar? think Manhattan liberals and The New York Times.) Lightfoot married this support with a respectable showing in Black communities across the South and West sides (frequently placing third behind conservative businessman Willie Wilson and the machine-aligned Toni Preckwinkle) allowing her to eke out a first place finish on the initial ballot with seventeen percent of the vote, where she advancing to the runoff and coasted to victory on her distance from the political establishment - winning every Ward in the City. 

On the contrary, Eric Adams narrowly won the Mayoralty primarily off the strength of Black and Latino middle and working class voters - as, amongst the City’s white electorate, he solely performed well with Orthodox and Hasidic Jews. Adams, a loyalist of the Brooklyn Democratic Party, ran an aggressive campaign emphasizing public safety, and remained consistently unpopular amongst the liberal, anti-machine electorate that embraced Lightfoot in Chicago.

Now, Lightfoot is in a fight for her political life. Hemorrhaging support, the besieged incumbent is facing eight challengers, six of whom are Black. Without ranked choice voting, the City’s three largest electorates - which breakdown across racial lines - are pitted against one another in a zero-sum game to advance to the April 4th runoff. This dynamic, which Black leaders have highlighted as the campaign has worn on, could significantly hinder the incumbent Lightfoot - who is facing stiff competition for the City’s Black vote, particularly from Brandon Johnson and the aforementioned Willie Wilson - whereas Jesus “Chuy” Garcia (Latinos) and Paul Vallas (Whites) have an easier path to coalescing their racial cohort - the latter of which will likely splinter along ideological lines.

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Paul Vallas

VIBES: Less wealthy Michael Bloomberg (Registered Democrat version), Self-aware Mario Procaccino

Paul Vallas enters Election Day as the prohibitive favorite to advance to the runoff election, and for good reason. While the former CEO of Chicago Public Schools netted only 5% of the vote in 2019, Vallas stands to benefit from positioning himself as the “law and order” candidate at a time when backlash narratives concerning rising crime have dominated the campaign trail.

A political outsider who has never held elected office (despite multiple attempts), Vallas’ flirtations with the Republican Party and courting of Chicago’s right-leaning police union bears resemblance to former New York City Mayor, Michael Bloomberg. As the only non-Hispanic white candidate in the race, Vallas is well-positioned to capitalize upon the crowded field and gobble up support from middle-class whites in the City’s Northwest neighborhoods. 

Despite appearing like a lock to advance to the April 4th runoff, whether Vallas ultimately makes his way to City Hall is dependent upon his ability to make inroads with both high-income liberal whites in North Center, Wrigleyville, Lincoln Park, and the City’s various historic districts and Black and Latino voters along the West and South sides. 

As more national media coverage hones in on Vallas, he will continue to polarize Chicago’s electorate. His weaknesses remind me of a more disciplined version of Mario Procaccino, an Italian-American former New York City Comptroller and Democratic nominee for Mayor in 1969. Dismissed by a majority of the electorate as a one-trick-pony, Procaccino rode his singular message of law and order to a stunning primary upset over former Mayor Robert F. Wagner Jr. and liberal stalwart Herman Badillo, fueled by a conservative backlash in the outer boroughs, before ultimately unraveling in the general election against incumbent Mayor John Lindsay (running on the liberal party ballot line), who won a plurality with Manhattan white liberals, Puerto Ricans in the South Bronx, and Blacks in Harlem and Bedford-Stuyvesant. Interestingly, Procaccino’s narrow victory in the Democratic Primary, where he captured less than one-third of the vote, inspired New York City (in part) to adopt runoff elections in party primaries, in order to prevent hyper-polarizing candidates from eeking out narrow wins if too many other candidates split the vote.

Vallas’ veiled racial messaging to “take our city back” is reminiscent of Procaccino infamously telling a Black audience, “my heart is as Black as yours.” Should he advance to a runoff, as predicted, the heat will turn up on Vallas - who could be felled by a Black-Latino coalition similar to the one that defeated Kathryn Garcia less than two years ago.

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Jesus “Chuy” Garcia

VIBES: Herman Badillo of Chicago’s Mexican community, Citywide Adriano Espaillat

While the Hispanic populations in New York City and Chicago comprise a nearly identical percentage of each city's populace, a key distinction must be made. In New York City, the Hispanic population is quite diverse, with hundreds of thousands of Dominicans (Upper Manhattan, West/Central Bronx), Puerto Ricans (South/East Bronx, East Harlem, Lower East Side, North Brooklyn), Mexicans (Sunset Park, Bushwick) and South Americans (Jackson Heights, Corona, North Corona) - whereas in Chicago, approximately 80% of the city’s Hispanic population is of Mexican descent.

This harkens back to an era when Puerto Ricans comprised an overwhelming majority of New York City’s Latino community - a time where demographic surveys in The New York Times simply listed “Whites, Blacks, and Puerto Ricans”. 

It is amidst this period where I found my New York City politics comparison for Chuy Garcia: Herman Badillo - a former Congressman (the first Puerto Rican to serve in the House) and Bronx Borough President, the Caguas-native ran for Mayor in three consecutive elections between 1969 and 1977.

Editor’s Note: For the purposes of this piece we will conveniently forget that Badillo launched an ill-fated bid for Mayor in 2001 as a Republican, where he was thoroughly crushed by Michael Bloomberg by a 3:1 margin.

Both Badillo and Garcia rose to power by challenging their local Irish-led political machines, with Badillo defeating State Senator Ivan Warner, an ally of County leader Charles Buckley, for the Bronx Borough Presidency in 1965 - while Garcia, supported by Mayor Harold Washington, bested Frank Stemberk, the handpick of Cook County Democratic Chair, Edward Vrdolyak, by less than 60 votes - dealing a critical blow to “Fast Eddie’s” efforts to obstruct the Washington Administration.

While Badillo’s ascension to Congress came much quicker than Garcia’s, the former always had his eye on the Mayoralty - finishing a close third in the aforementioned tilt that featured Procaccino, Robert F. Wagner Jr, and Pulitzer Prize winner, Norman Mailer. Had Wagner not been summoned to return from his post as Ambassador to Spain, Badillo, a liberal favorite for his championing of the urban poor, would have picked up countless votes from Manhattan’s liberal intelligentsia, but not enough to outlast the Procaccino backlash of outer borough working class whites. Despite advancing to a runoff against Abe Beame four years later, before finishing a distant sixth place in the hotly-contested ‘77 race, the ethnic arithmetic of New York City (at the time) did not lend itself to a Badillo citywide victory. Against the likes of Ed Koch, Bella Abzug and Percy Sutton - Badillo saw his coalition contract, losing White liberals and Blacks who once enthusiastically backed him, leaving him unable to advance forward on the Latino vote alone.

In contrast, Garcia did not publicly consider running for Mayor until thirty years into his political career - bouncing around between the City Council, State Senate, and Cook County Board of Commissioners before ultimately launching a high-profile 2015 bid against incumbent Rahm Emanuel. Recruited by Chicago Teachers Union President, Karen Lewis (who was once poised to be a formidable contender before being sidelined due to worsening health), Garcia staked himself as the progressive candidate in the race, winning the endorsement of Senator Bernie Sanders. Despite advancing to a runoff and winning significant margins with Latino voters - an impressive feat against a well-funded incumbent - Garcia could not crack the cache President Obama’s former Chief of Staff had accrued with Black voters on the South Side - whom he lost by an aggregate of twenty points - and wealthy white voters adjacent to the Lakefront, who overwhelmingly backed the incumbent by an average margin of 4 to 1.

A crucial variable that helped ensure Garcia reached the runoff eight years ago was his staunch progressive support. Yet this time around, he has lost several marquee endorsements, including the coveted Chicago Teachers Union, to Cook County commissioner Brandon Johnson, who joined the race last October intent on upholding the proverbial progressive mantle at a time when Garcia wavered on his commitment to the campaign. Even since entering the contest, Garcia has been charged with running a lackluster effort that has fractured Chicago’s progressive movement, potentially setting the stage for Vallas and Lightfoot to advance to the runoff. Amidst a more competitive field, Garcia risks his baseline of support with white progressives, liberals, and black voters regressing to the point where he misses the runoff entirely - an unimaginable scenario when he entered the race just four months ago.

Like Adriano Espaillat, Garcia has one of the most progressive voting records in all of Congress, but has staked out more moderate positions at the local level, especially with respect to crime and policing during this Mayoral campaign. Akin to the Dominican power broker, Garcia has cultivated a deep network of Latino legislators along Chicago’s West Side, a sphere of influence the Mexican Mayoral candidate has sought to grow, which has occasionally precipitated conflict with the progressive left - most notably “his endorsement of Samie Martinez, a police union-backed candidate challenging Chicago Alderwoman Rossana Rodriguez-Sanchez, a democratic socialist.” 

By essentially seceding the ascendant activist left to Johnson, Garcia is betting on robust turnout amongst the Latino community and that his decades-long progressive record can swing enough undecided middle-class Blacks and liberal whites, who value the Congressman’s left-bona fides, but view Johnson as an ideologue. 

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Lori Lightfoot

VIBES: If Bill de Blasio ran for a third term, Abe Beame facing six challengers in 1977

While Lori Lightfoot is oft-compared to Eric Adams by the media, her electoral path to City Hall and tenure as Mayor, bears a closer resemblance to Adams’ predecessor - Bill de Blasio. 

The two endeared themselves to liberals with promises to increase accountability and reign in their respective police departments - with Lightfoot touting her experience chairing a special task force to investigate the police killing of LaQuan McDonald, while de Blasio preached racial harmony in an iconic ad featuring his biracial family in addition to railing against Bloomberg’s “stop and frisk” program - efforts that culminated in resounding victories for both. 

While Bill de Blasio’s popularity slowly cascaded following the height of his election, Hizzoner managed to stave off a rumored challenge from Comptroller Scott Stringer in 2017, before being term-limited four years later. Yet, Lightfoot would not be so lucky, assuming office less than one year prior to the onset of the COVID-19 pandemic, which gave rise to a precipitous increase in killings across Chicago over the next two years - quickly turning crime into the most salient issue of the 2023 Mayoral Race.

With urban centers across the United States reeling following the pandemic - wrestling with rising crime, high inflation, worsening health outcomes, and an erosion of commercial real estate value - Lightfoot’s support amongst white liberals, the preeminent force behind her 2019 triumph, has begun to wane - leaving her to increasingly rely on the City’s Black voters to keep her runoff hopes alive. This coalition shift, born out by years of polling and ideological realignment, was also reflected in de Blasio’s final years in office, and became increasingly clear upon his failed run for Congress in New York’s 10th District.

Lightfoot finds herself in a position akin to that of Abe Beame, the diminutive ally of Meade Esposito who presided over New York City’s fiscal meltdown during his first term in office, only to be greeted by six ambitious challengers at the height of the City’s economic and social upheaval. While Beame and Lightfoot, as politicians, could not be more different - with Beame a creature of the Brooklyn Democratic machine and Lightfoot an anti-establishment outsider - the precarious and dire nature of their re-election circumstances bind them together. The uncharismatic and increasingly unpopular Beame ultimately finished in third place, behind the more dynamic characters of Ed Koch and Mario Cuomo.

While someone like Eric Adams can consistently bank on support from working and middle class Black voters, Lightfoot’s strongest support four years ago did not from those aforementioned precincts. In fact, many pundits were originally doubtful of Lightfoot’s candidacy because she lacked an obvious electoral base, preferring to brand herself a coalition candidate divorced from the very political institutions that Adams matured within. Lightfoot’s lack of a durable relationship with Chicago’s political institutions could break her campaign this time around, after having made it four years prior. Given her atrophy amongst the white electorate, the incumbent has been forced nonetheless to try and carve out a meaningful base of support on the South Side - a tall task when facing six other Black candidates. 

To do so, Lightfoot has gone on the offensive, employing some Adams-like rhetoric in the process, calling her Black opponents “false prophets”, who risk letting political power “go to another part of town,” while asserting that a vote for "somebody not named Lightfoot is a vote for Chuy Garcia or Paul Vallas. If you want them controlling your fate and your destiny, then stay home.” 

As she has leaned into more divisive rhetoric, Lightfoot may be setting herself up to fail by narrowing her coalition. While she has made these remarks in predominantly Black neighborhoods, her attacks have been consistently covered by the press throughout the campaign, and could cost her dearly with civically-engaged white voters, especially if she makes the runoff. Yet, she may believe there is no other choice. 

While Eric Adams rode a public safety message into City Hall, Lori Lightfoot’s tenure as Mayor may be felled by a similar current.

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Brandon Johnson

VIBES: Apex Jumaane Williams

The choice of Chicago’s leading progressive institutions - from the United Working Families to the Chicago Teachers Union - and David Axelrod’s pick to join Vallas in the runoff, perhaps no candidate enters Election Day with more momentum than Brandon Johnson.

Since entering the race, Johnson has made significant strides coalescing the progressive vote, which was up for grabs at the start of the campaign. Increasingly popular with young renters and the activist left, Johnson is the only viable candidate who has not committed to filling the 1,600 vacant Chicago police department positions - in addition to facing criticism from his opponents for past calls to “defund the police.”

Redolent of an rising Jumaane Williams five years ago, Johnson is beloved by the Windy City’s “Alphabet Left”, yet still maintains a degree of cache with working class Black voters, particularly in his home neighborhood of Austin. At the apex of Williams’ coalition, he remained equally popular with progressive whites and Black voters in Brooklyn, from homeowners to public housing residents. 

However, it is important to consider that, absent civically-engaged liberals bordering Lake Michigan, New York City’s white electorate, particularly in Manhattan and along waterfront communities Brooklyn and Queens, is far more ideological as a whole than Chicago’s - and in turn, more left-leaning, creating a more hospitable electoral environment for progressive candidates like Williams and Johnson. Yet, in the Windy City, the share of progressive and liberal whites compared to the electorate at large is considerably smaller, narrowing Johnson’s prospective coalition.

Not to mention, throughout all of his citywide campaigns, Williams never had to contend with another prominent Black candidate, whereas Johnson must remain competitive with Black voters against both the incumbent Mayor and popular businessman Willie Wilson, who are channeling their eleventh hour efforts into winning voters on the South Side. 

A perennial candidate for office, the aforementioned Wilson remains a pivotal figure in shaping the outcome of Tuesday’s election. The son of a Louisiana sharecropper, Wilson established himself as a McDonald's franchise owner, latex glove importer/exporter, and gospel music television producer before running for Mayor in both 2015 and 2019. Despite a lack of ties to the City’s political institutions, save for an endorsement from the Cook County Republican Party, Wilson broke ten percent of the vote each time, including winning thirteen predominantly Black wards (the most wards of any candidate) four years ago, indicating the raw depth of his base. While not tapped by many observers to advance to the April 4th runoff - given that his electoral performance flatlines with Whites and Latinos - Wilson’s prohibitive strength with more conservative Black voters ensures he is a safe bet to take home between 9-12% of the vote. While the only non-Democratic Party affiliated candidate in the race, Wilson will almost assuredly lose out to Paul Vallas amongst Chicago’s white Republican voters.

Think of Wilson as having the working class appeal that New York City liberals feared fellow-Trump supporter, Rubén Díaz Sr. had in the 2020 open primary for New York’s 15th Congressional district.

It is hard to imagine a scenario where a meaningful number of past Wilson supporters abandon his candidacy, either for the besieged Lightfoot or the left-leaning Johnson, given the former finished behind Wilson in every majority-Black precinct four years ago.

To advance to the runoff, Johnson must remain competitive with Lightfoot amongst Black voters, take 10% of the Latino vote (assuming Chuy will win 75+%), dominate with progressive voters in wards represented by DSA electeds, and best both the incumbent Mayor and Congressman Garcia along the liberal Lakefront corridor. If Johnson prevails and enters into a runoff against Vallas, he would have multiple avenues to rebuild the ever-elusive “Rainbow Coalition” - but does he lack a strong enough base to get there in the first place?

In a campaign defined by racial politics, ideology may have to wait.

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