I'm Worried About Chicago

I am writing this Newsletter while I am back visiting Chicago and seeing friends and family. I was born and raised in this city and come back every year. I can see that it has undergone the “New American Urbanism” change that many big American cities went through during the last 20 years. When professionals started moving back into American cities instead of just going to the suburbs.

• Expensive Real Estate

• Bicycle Lanes

• Coffee Shops

• Upscale Clothing Stores

• Yoga Studios

• Interesting Restaurants

• etc

Chicago is still peculiar though, because it isn’t really known city or has a brand of its own but it is big, much bigger than the other cities in the midwest. It does get disrespected by coastal elites a lot.

What is Chicago?

When I mention I'm from Chicago during my travels in Europe, many recognize the name but can't pinpoint its significance. Even within the US, its identity remains somewhat elusive. Other cities have clear associations: New York is known globally as America's financial and cultural hub, San Francisco as the tech center, Las Vegas for gambling, Miami for its beaches and vibrant nightlife, and LA as the heart of entertainment. But Chicago's defining characteristic? It's harder to articulate.

Chicago defies easy labels. Urban planner Pete Saunders once described it as "1/3 San Francisco, 2/3 Detroit." In a talk he delivered in the city, Peter Thiel remarked, "If you're truly exceptional, you either head to New York or Silicon Valley." His implication? Chicago isn't a magnet for the global elite. And there's some truth to it. Chicago pulses with a distinctly American vibe. It resonates more with its neighboring rust belt cities—Milwaukee, Detroit, Cleveland, or Pittsburgh—than international hubs. Yet, it stands apart in its affluence, towering above these counterparts in wealth.

Chicago boasts formidable assets. It's home to a myriad of corporate headquarters, and it anchors the world's paramount financial exchange: the CME Group. These financial titans, long regarded as the pivotal force in the global derivatives market, steer a staggering $75 billion industry.

It has elite universities (Northwestern and the University of Chicago), a major hub airport (O’Hare), and offers Americans an opportunity to live in a real city.

• The city has a magnificent lakefront setting

• A big expanse of true urbanism in a nation where high-quality urban neighborhoods are in short supply. It has neighborhoods that are walkable like Lincoln Park, Wicker Park, Andersonville, etc.

• It also has a mini-manhattan downtown called the Loop 

The only real flaw is the terrible, terrible winters. The cold can be deeply felt, and the wind often intensifies the chill. The streets, which are familiar and lively in other seasons, become challenging to navigate due to ice and snow. Visibility decreases as breath becomes visible in the cold air. The lake, a hub of activity in summer, becomes desolate and frozen. Activity on the streets slows down as residents move carefully to avoid icy patches. The usual hum of the city quiets, and indoor spaces like cafes and bookstores become sought-after refuges from the cold.

Why Am I Worried?

The pandemic left its mark on every American city, like the diminished occupancy in downtown offices, that are not unique to Chicago; cities like San Francisco echo these sentiments. Presently, only 54% of Chicago's workforce has returned to their offices. Even if this were to climb to 70%, it paints a bleak picture for owners of towering office spaces who banked on 90% occupancy. When these skyscraper values tumble, so do sales and property tax revenues, leading the city's budget into a treacherous dance and triggering a cascade of economic repercussions.

Distressed office space being a problem in Chicago isn’t like a big deviation from national trends. Yet, my focus isn't on these commonalities. I'm drawn to the nuances unique to Chicago, issues that may either prove stubborn to mend or guide the city down an unprecedented avenue.

In This Newsletter

I will explain the reasons why I think Chicago may be entering a pivotal time in its history.

1) What Does Decline Look Like? Decline does not have to mean a Mad Max situation. Lots of cities are in decline but people still live in them and go about their business. I believe Chicago will always be a city that functions and works, just worse off in its’ own unique way.

2) Crime: For as long as I can remember, there was an unspoken agreement. The high crime rates in Chicago only existed in certain neighborhoods. Recently, crime is spilling out into neighborhoods that never experienced much crime before. Why would this ever stop now that this line has been crossed?

3) The Bernie Sanders Revolution Comes to Chicago: What if Bernie Sanders ran for Mayor of Chicago instead of running for president? How well could his policies work in a major US city? We’re about to find out.

4) The Worst Deal in History: Chicago signed probably the worst government deal in history. You probably haven’t heard about it. It involves leasing parking meter revenue for 75 years to the United Arab Emirates in exchange for a one-time payoff to close a budget hole.

What Does Decline Even Mean?

When you say that a city is in decline to an American, in their head pop-up images of Baltimore or Detroit. Really, the worst cases.

A decline in a city doesn't necessarily equate to dysfunction or poor living conditions. A city can remain functional while it's experiencing a decline. This is evident in places like Naples, Italy. Many tourists who visit Italy often explore cities like Venice, Florence, and Rome. However, when they arrive in Naples, they're surprised by its condition, especially when compared to the other Italian cities they've visited.

It’s true, Naples is in decline. There is dysfunction on so many levels. Currently, it is probably at its lowest point in its thousand year + history. The decline mostly began after the 1970s and has increased. You can watch the 1972 Billy Wilder film Avanti! and see Naples look much better than it does now. Or you can peruse archival footage.

Naples is a real city though, with people living in it. It has over two million people living in it permanently. Compare with Venice, an Italian museum city, the permanent population of Venice has gone from 175,000 in the 1950s to below 50,000 today. Venice is not a real city. Naples is an amazing place to walk around. It is intense but very stimulating. There is charm to Naples even as it is in decline.

How Do You Stop a Crime Wave?

I've spent a significant amount of time living in Europe and have observed that Americans, on the whole, seem more accustomed to higher levels of crime in their societies. If an American were informed about a shooting in a nearby park, many might see it as an unfortunate but not uncommon event in urban life. In contrast, many Europeans would be deeply alarmed by such news and would likely call for increased police presence and security. From an American perspective, Europe seems to have almost no violent crime. Personally, I always felt safe in Europe, even when walking through cities late at night.

American cities went through an intense crime wave during Covid. It has mostly declined in New York City. Through the first six months of 2023, New York City has seen reductions in five of the seven index crime categories, including murder down 7.9% (199 v. 216), rape down 9.9% (729 v. 809), robbery down 4.8% (7,789 v. 8,180), burglary down 9.9%. The city elected a cop with the explicit mission of lowering crime and he has succeeded.

However, in Chicago, crime has just kept going up. Robbery reports are up 24% from last year and 30% from 2019, the last year before the pandemic. But the story is much worse in certain districts. Compared to last year, robbery reports are up 59% and 53% respectively. They’re up 78% and 96% versus 2019. The increase is primarily due to armed robbery sprees. Small groups of young men, usually traveling in stolen cars, sometimes commit more than a dozen robberies at a time. The robberies are usually a violent encounter.

• DePaul students being pistol whipped

• Waiters being gunned down walking home after their shifts

• 78 year old man beaten during robbery raids

Chicago has historically struggled with a high crime rate. However, what's notable about the recent surge in crime is its location. Traditionally, crime was largely concentrated in the South Side and West Side, areas often associated with poverty and minority populations. In contrast, the more affluent Northside was typically safe and experienced minimal violent crime. Now, this surge is predominantly occurring in the Northside.

Chicago has the highest number of gang members in the U.S., with around 150,000 individuals affiliated with over 100 different gangs.

Many of these individuals choose not to participate in the legal economy. Historically, these gangs mainly clashed amongst themselves, with civilians usually remaining unaffected. However, recently, there's been a noticeable shift with gangs targeting ordinary citizens for robberies. This is a departure from the past, something I've never observed before.

Addressing this change will require a novel approach, given its unprecedented nature. It's uncertain whether any strategy will be effective.

If this trend continues, Chicago might see an uptick in street robberies during the night or early morning, eventually becoming an accepted part of daily life.

The Real Left Takes Power in Chicago

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