The non-stop headlines cannot help but evoke the classic account of stupidity, futility, and doom
There are weeks when writing a column requires effort. And then there are weeks when Chicago’s mayor — hereinafter “His Honor” — does the work entirely on one's behalf. Increasingly, the latter outnumber the former. In the spirit of humility, I must admit it is a rare professional delight to cover an administration so committed to self-parody that your correspondent is reduced to the role of a stenographer, dutifully recording each fresh absurdity.
Under His Honor’s misrule, Chicago’s government has become a kind of perpetual-motion machine of ineptitude. One need only observe, chronicle, and publish his loser litany.
It helps that Chicago remains resolutely blue — so blue even the Chicago Tribune, once considered the city’s conservative bastion, now reads like Pravda. Our institutional press has merged seamlessly with aldermanic talking points; the headlines alone serve as milestones on the city’s downward path.
For his part, the mayor produces these headlines at a rate that would exhaust the most caffeinated pundit. One almost admires the consistency. He is clearly a man devoted to his craft — and that craft appears to be providing an ongoing case study in what happens when ideological zeal outpaces rudimentary administrative competence.
His Honor’s hapless reign cannot help but evoke the famous stanza from Alfred Tennyson's The Charge of the Light Brigade:
“Forward, the Light Brigade!
Was there a man dismayed?
Not though the soldier knew
Someone had blundered:
Theirs not to make reply,
Theirs not to reason why,
Theirs but to do and die:
Into the valley of Death
Rode the six hundred."
Could any description better fit the pin-headed minions who continue marching in lockstep behind his blunders, lances of failed policy falling from their cold, dead hands (politically speaking, of course)?
One suspects he commands at least 600 such functionaries; his 150-strong mayoral security detail alone gets him a quarter of the way there. But all the king’s horses and all the king’s men cannot put the Humpty Dumpty that is His Honor back together after his fall — plummeting from the thrill of victory to the agony of serial, crushing political defeat.
No one expects a mayor to be a budget savant. Richard M. Daley certainly wasn’t. But one does expect a basic familiarity with numbers — preferably whole numbers, though fractions would be nice — particularly when calculating the percent of tax dollars annually poured down the sewer grate that is the Chicago Public Schools.
His Honor, however, displays a level of innumeracy typically associated with the victims of severe educational malpractice. “Fiscally illiterate” may be the kinder phrasing, but the evidence suggests a more comprehensive abdication of the administration’s fiduciary obligations — dereliction of duty masquerading as “progressive innovation.”
In many ways, his election marked the apex of progressive fantasy: The belief that government could be reinvented through pure moral preening. “If we can elect this man,” activists reasoned, “we can elect anyone.”
Perhaps they overshot.
In criminal justice circles, it is said that a grand jury can indict a ham sandwich. Your correspondent regrets to inform you that His Honor is, politically, a ham sandwich — and a stale one at that.
His major policy ventures have collapsed with startling speed.
His signature ballot initiative, the “Bring Chicago Home” referendum — touted as a moral crusade — failed spectacularly. In a city where progressive referenda usually pass with all the suspense of a Soviet election, this one lost decisively. The only people unsurprised were the voters.
Then came the budget. Presented to an all-Democratic City Council — one-fifth of whom are democratic socialists — His Honor’s fiscal blueprint united the chamber … entirely against him. To lose a budget vote in a room without a single Republican is a political nadir no known blue city mayor in American history can claim. To lose it overwhelmingly is something else entirely.
At one point the Council delivered a 50–0 rebuke. Let that sink in: The big 5-0. Zero. Nada. Zip.
Even His Honor’s supposed loyalists struggled to conceal their embarrassment.
Chicago’s lineup of past mayors has included fools and knaves. Still, even the dimmest of the Daleys would never have brought such a dead letter to their puppet council — let alone seen it defeated unanimously. The mere possibility would have reduced their alders to trembling heaps. The Daleys, referred to with awe as “The Man on Five,” ruled as emperors of their personal Empire by the Lake; their political mistletoe was dutifully kissed by all who wished to survive.
By contrast, our contemporary His Honor commands no such respect. He is the first Chicago mayor whose own party treats him as a nuisance rather than a Napoleon. Little wonder he reportedly suffers from panic attacks. At least City Hall provides excellent health insurance.
Even Lori Lightfoot — whose legacy was, until recently, considered politically unrecoverable — now benefits from the comparison. And Rahm Emanuel, that sailor-tongued, hyper-competent terror of City Hall, looks like a reincarnation of Pericles beside him.
During his campaign, His Honor offered a “read my lips”-style pledge on property taxes. Those familiar with George H.W. Bush’s experience could have predicted how this vow would age.
Sure enough, the administration soon rolled out a property tax hike, defended with the sort of rhetorical gymnastics usually reserved for pre-digital children explaining why the dog ate their homework. Even his own floor leader refused to carry the water. The mayor, meanwhile, insisted as late as December 8 that no one could know whether his budget had 26 votes “because the vote has not yet been taken.”
Apparently, he has not heard of the political position of whip, perhaps an educational deficit resulting from not at least minoring in political science.
His attempt to influence the Chicago Board of Education — a body largely composed of people who should be friendly to him — failed in a manner reminiscent of the Light Brigade: brave, perhaps, but strategically suicidal. Losing a vote in a chamber you effectively control is rare. But His Honor is a man of rare talents.
Then came the open revolt. Alderman Samantha Nugent (39) accused him of precipitating an unprecedented shutdown of city government, comparing him to his bête noire, “Orangeman Bad.” One could almost hear the mayor whispering, “Et tu, Samantha?” as the Council lined up to stick political shivs through his toga. An appropriate soundtrack for this tragicomedy might be “Symphony Chapter 9.”
Meanwhile, His Honor presides over the constriction of arterial streets, shrinking four lanes to two in order to install bike lanes protected by concrete medians. The problem? Chicago’s winter cyclists number roughly the same as the remaining dodos, while motorists — actual voters — find themselves stuck in glacial traffic.
Their backlash was immediate: Demonstrations, honking, signs, and the general ambiance of peasants storming the Bastille. One imagines they will remember this at the polls — early and often, as the Chicago maxim goes.
As I write, television reports show furious residents confronting city officials over triple-digit property tax hikes used to feed the monstrous, failed Chicago Public Schools system.
Chicago has survived corruption, economic shocks, and demographic churn. But resilience has limits, and those limits are now being probed with uncommon vigor by a mayor whose internal compass appears factory-calibrated to magnetic south.
For journalists and political observers, this is manna from heaven — grist for the mill where, in the immortal words of Finley Peter Dunne’s Mr. Dooley, “Politics ain’t beanbag.”
But for the city’s 2.7 million residents, it is considerably less amusing.
Cities rarely collapse all at once. More often, they deteriorate through accumulated misjudgments and leaders who believe that ideological fervor can substitute for competence. Chicago may be approaching that threshold.
Far be it from this correspondent to prescribe solutions. Yet the electorate tends, eventually, after exhausting all alternatives, to do the right thing. And His Honor’s approval ratings in this deep-blue burg have reached record lows — approaching zero, as University of Chicago economists might put it, asymptotically.
Chicagoans of good judgment — and Contrarian readers are so blessed — can draw their own conclusions.
Ours is but to document the spectacle of Stupid City Hall Tricks for your consideration, secure in the knowledge that, on Election Day, you’ll know what to do.

