The Downfall of America's Cities: Chicago's Descent Into Socialism

Oct 23, 2026 2:30 PM
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The Downfall of America's Cities: Chicago's Descent Into Socialism
Stormy Petrel, the dark harbinger. (Credit: Ward Clark via AI - Night Cafe Creator)
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Given that I remain a happy resident of a small rural community in Alaska, it's still something of a curiosity that I'm still writing about the state of America's urban areas and Democrat/leftist (but I repeat myself) jurisdictions. If you've been reading my work over the last few years, you know I grew up in a rural community in Iowa and am now a content rural dweller myself. I have little time for cities, despite having lived in them for four decades. I find them unpleasant; crowded, noisy, and, to be honest, they smell bad. I like being able to go outside in the early morning here in the Susitna Valley to clean air and ice-chip stars, and if that means I have to put up with the occasional overnight temps at 20 to 30 below, that's fine.

So, why am I still worried about America's cities? Because our cities are the beating hearts of our nation. Much of the country's economic activity happens there. Urban areas host much of the country's industry and academia. What's more, our cities used to be the pride of the nation, but that's less the case now. Too many of our nation's cities, large and small, are beset with repeat criminals, and in some cases, those crooks are the people who are supposed to be protecting the people.

Case in point: Chicago, which long ago fought a battle with socialism, which the Windy City won — but now that battle is back, and there's no guarantee the proponents of liberty and property will win this time. Socialism isn't a new thing in Chicago; in fact, it began even as Karl Marx was first preaching his pernicious gospel in Europe. In Chicago, this took the form (in part) of the Haymarket Affair, a mass protest on May 4, 1886, at the McCormick Harvesting Machine Company, when police intervened to protect strikebreakers. The strikers had the sympathies of Chicago Mayor Carter Harrison, who described the event as "peaceful" (the only thing he missed was the "fiery but mostly" part). But this was supported by openly socialist members of the Chicago City Council, and the Council had socialist members until the post-World War II era, when the movement there faded away.

This isn’t the first time socialists have sat on the Chicago City Council. In the 1870s, the Socialist Labor Party, created in response to the labor violence of the Gilded Age, elected five aldermen. The movement was suppressed after the 1886 Haymarket Square bombing, but at the turn of the 20th century, the Socialist Party of America emerged. In 1917, three Socialist aldermen sat on the council, using their positions to oppose U.S. participation in World War I. When Alderman John C. Kennedy spoke out against a resolution granting city employees time off to register for the draft, one of his colleagues taunted, “Why don’t you bring a red flag to the Council?” The party’s popularity declined as a result of the postwar Red Scare.

But like a bad penny, it seems socialism/communism always comes back around. In the case of Chicago, the resurgence of the far-left came after the end of the Daley dynasty.

Yet those radicals and organizers remained resolutely committed to their cause, often squabbling with the Daleys and other mainstream Democrats. The most infamous of these figures was Saul Alinsky, author of Rules for Radicals. He was the subject of Hillary Clinton’s senior thesis at Wellesley, and the community-organizing tradition he pioneered influenced Barack Obama, who worked as an organizer on Chicago’s South Side before launching his political career as a young lawyer. The future president also worked on a philanthropic venture with University of Illinois Chicago professor Bill Ayers, cofounder of the Marxist terrorist group the Weather Underground, which carried out bombings of the U.S. Capitol in 1971, the Pentagon in 1972, and the State Department in 1975.

Fast forward to today. There are six card-carrying members of the Democratic Socialists of America (DSA) on the Chicago City Council, making up 12 percent of the aldermen in that group. That may not seem like a lot, but it's the highest percentage of openly socialist politicians in any major city council in over a century. We're accustomed to thinking of places like Portland, Oregon as hotbeds of the DSA, but it's Chicago that's being slowly co-opted, with a growing number of open socialists on the council and a mayor who sympathizes with the far left, while also being not only one of the least competent leaders in Chicago's history (and in that, he's up against some pretty stiff competition).

Now, the DSA and its commie fellow travelers are taking this show on the road. They are subsuming Chicago, and we hasten to note that the actual socialist caucus in Chicago doesn't rule out at least some socialist proclivities among the Council's other members. We have seen a Democratic Socialist mayor elected in New York, Zohran Mamdani, who is proceeding to implement the socialist policies that always lead to ruin, and next month, we could very well see the election of DSA-aligned Nithya Raman as Mayor of Los Angeles, although we admit that in this election Los Angelenos are between the rock of Karen Bass's overwhelming incompetence and hard place of Nithya Raman's communist tendencies.

Our major cities are at a tipping point. Will socialism continue to make inroads into our major cities? If it does, then we can expect the true believers in socialist/communist policies to try to expand into the suburbs and even small-town and rural areas. Or, will socialism fade away, driven off by its own failures?

The next two election cycles will tell the tale. As time goes on, I'm more and more convinced of this; the 2026 and 2028 elections will chart the course for American history for, quite possibly, the rest of the century — and who wins will define whether or not what we have in store for us is an American century, or not.

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