There is a path to dislodge progressives from office, but will moderate Democrats and Republicans follow it?
One week prior to Chicago’s March 17 primary date, there was every indication Alderman Brendan Reilly (42) was running a competitive race in the Democratic primary for president of the Cook County Board. Among many of Reilly’s supporters, there was a glimmer of optimism Cook County Democratic Party boss Toni Preckwinkle would finally, and mercifully, be turned out of office.
Then, one day ahead of voters heading to the polls, the unthinkable occurred: A M3 Strategies survey revealed Reilly was headed for a thumping at the ballot box. In its polling memorandum released March 16, M3 projected Preckwinkle would defeat Reilly decisively. The day after voters rendered their verdict, Preckwinkle emerged victorious, winning with a startling 68 percent of the vote.
An outcome which, more or less, was unexpected 24 hours before polls opened, Toni Preckwinkle’s soul-crushing victory over Brendan Reilly is to a lesser extent attributed to late momentum in her favor or a dramatic surge in progressive voters, but more likely to ill political fortune, a few foolish missteps, and a serious flaw in his campaign strategy.
Of the many messages Cook County voters delivered when they returned Preckwinkle to office on March 17, the principal message is woke, Diversity, Equity, and Inclusion (DEI) liberalism prevails in Chicago. Though wokeism remains a communicable brain-eating malady, to the uncompromising, absolutist, social justice activists on the far Left to whom victimhood and sensitivity to social issues is paramount, Preckwinkle remains the darling of under-represented groups.
Reilly’s poor performance in the race can also be assigned to low voter turnout: An anemic 27 percent of the city showed up to vote. Though few eligible voters did show up at the voting booth, Lakefront voters — many of whom are committed progressives — flocked to polling places to grant a reprieve to the Board president. A well-heeled bastion of woke, pro-choice, feminist, and secular thought, while Preckwinkle is irredeemably flawed, her complications were not abundant enough for voters along the lake from the South Loop to Edgewater to stomach pulling a lever for a moderate Democrat. Worse for Reilly, while this Lakefront Leftist bulwark cannot be so easily overcome, Reilly failed to woo voters in areas of Chicago which tend to favor moderate Democrats and a handful of Republican voters — the Northwest and Southwest sides.
Moreover, Preckwinkle was also aided by a slight jump in turnout among younger voters. Exit polling revealed nearly 85,000 voters between the ages of 18 and 34 cast ballots, up from 62,000 four years previous. While this upsurge in support from younger voters did not pull Preckwinkle past the post, it serves as an ominous portent for the future: A newer, younger, more ideologically disciplined progressive electorate — kiddie progressives brainwashed by the warped minds at the CTU — are of voting age and are participating in elections.
In one miscalculation, Reilly directed attacks at Mayor Brandon Johnson and summoned the specter of Kim Foxx rather than concentrating on Preckwinkle’s blunders, unwise decisions, and autocratic governing style. Though Reilly’s plan to assail Preckwinkle for her botched handling of the Tyler Technologies contract, mismanagement of Cook County Health, and the County budget tripling under her terms was a sober campaign plank and a sound strategy for victory, his tactic of using Chicago’s inept mayor as a cudgel to bludgeon Preckwinkle drew unanticipated consequences.
A plan which spectacularly backfired — Preckwinkle cleverly declined to respond to the provocation — Reilly conjuring up the memory of the comically incompetent Foxx and hurling brickbats at Chicago’s bungling mayor appeared to be the 42nd Ward alderman mocking and casting withering scorn at one former black officeholder and two black elected lawmakers. A remarkably short-sighted tactic, by stubbornly sticking to lambasting Johnson, Reilly only negated any gains he made among undecided black voters.
Preckwinkle also clinched the victory due in part to Reilly’s faint responses to the Board president’s baseless attacks. While Preckwinkle’s contention Reilly was a covert Trump supporter may have convinced some of her gullible supporters, the consistency with which she hurled the ridiculous charge had a lasting effect. To his credit, Reilly did address the allegation; however, simply shrugging off the false assertion with a chuckle rather than passionately denouncing the claim as absurd and responding by branding Preckwinkle a liar did little to bolster his campaign.
In another instance, Reilly insufficiently defended his position on criminal illegal aliens. Though Reilly did justify his support for a January 2025 vote to allow the Chicago Police Department police officers to cooperate with the federal government on the arrest of criminal illegal aliens, the irregularity with which he defended his position alienated voters who were frustrated with Preckwinkle’s slavish support for criminal illegals.
Despite his campaign being cushioned by deep-pocketed donors, and his clear and compelling message Preckwinkle was burning Cook County down with her bumbling leadership, Reilly’s fatal mistake was failing to directly connect with voters.
Though television and digital advertisements, phone banks, mass SMS texting, and mail are effective, winning campaigns do not limit themselves to political spots or glossy mailers. While Reilly did spend on several essential forms of advertisement to boost his campaign, his campaign failed miserably to develop and execute a field strategy — mobilizing volunteers to canvass neighborhoods — to promote awareness of his candidacy and convince voters to embrace his message. A significant strategic lapse on his behalf, by neglecting to assemble a committed brigade of volunteers to circulate on foot through Chicago’s neighborhoods and directly engage with residents to drum up support for his candidacy, Reilly denied his campaign countless potential votes.
Though canvassing a neighborhood is not an unprecedented campaign strategy, the collapse of the patronage system has left legacy wards without committed campaign volunteers. With the crumbling of the Daley-era patronage armies came a void, and this vacuum has today been filled by progressive activists.
Progressives grasp, in a way their political opponents do not, that in order to win elections a large-scale effort must be undertaken to build sustainable political networks in neighborhoods to directly engage with voters. An exercise referred to as "community organizing," perhaps the simplest definition of community organizing is the practice of identifying a specific aggrieved population — say residents of a blighted neighborhood — and agitating them until they become so flustered about the conditions in which they live, they take collective action to compel lawmakers to enact change.
Today, progressives control Chicago’s streets with the assistance of organized labor and the vast underworld of neighborhood non-profits, all of which swear fealty to progressive leaders in Cook County and Chicago. A mechanism which functions very similarly to the Chicago Machine, in exchange for generous contracts with the city and Cook County, organized labor — mainly the Chicago Teachers Union (CTU) and the Service Employees International Union (SEIU) — unions donate to progressive candidates and perform door-to-door canvassing for progressive office seekers during campaign season. Equivalently, in return for grants from the state, Cook County, and the City of Chicago, non-profit leaders use neighborhood non-profits as vehicles to rally on behalf of progressive candidates for office, mobilize an army of canvassers to spread the progressive gospel, and conduct voter outreach. Tax-bankrolled political activism, this built-in advantage is precisely what propelled Preckwinkle back into office.
All the money in the world won’t win elections
Brendan Reilly was an exceptionally qualified candidate for president of the Cook County Board. A man with a long and substantive resume in the private sector and in public office, Reilly was well funded and had a pragmatic, nonideological vision for Cook County. While Reilly should be laureled for having the political courage to challenge Preckwinkle for Board president, the gaping hole in Reilly’s campaign strategy was failing to develop a strong political network of committed volunteers for door-to-door solicitation.
There are many lessons to be learned from Brendan Reilly’s loss to Toni Preckwinkle. Paramount among them is money alone cannot win elections. While television spots and gleaming political mailers are effective, it is not an adequate substitute for bonds built between a campaign worker and residents. Second, moderate and conservative voters must rid themselves of the notion they will receive perfection in their candidates. Progressives elect deeply flawed candidates — many of whom are outright incompetent — and it keeps moderate and conservative voters home. Finally, bodies matter. Moderate and conservative voters must put forth an effort construct political networks — a web which is closely intertwined logistically, operationally, and strategically — in Chicago’s neighborhoods to compete with the progressive movement’s neighborhood power structures.
The groundwork for Chicago’s reversal of fortune hinges on moderate Democrats and Republicans building political networks in Chicago’s neighborhoods. The core obstacle before moderate Democratic and Republican candidates is whether they have the patience and determination to assemble stable, disciplined, mass-based power organizations across Chicago. Moderate and conservative candidates have the right messages and funding, yet they are missing out on connecting with countless voters. Until consensus-seeking candidates directly engage with voters through local political networks, they will not find themselves at an immeasurable disadvantage, they will continue to be locked out of office by progressives.
