People ask me all the time if I miss Chicago. We left Chicago for Las Vegas in 2020. There are certainly some things I miss. I lived there for my entire life. But reality slaps you in the face often when you visit or read the news coming out of Chicago and Illinois.
When I visit, I see stuff behind plastic in Walgreens, or on the way out, if I need a bag, I get to pay the Rahm Emanuel bag tax. I get to drive on potholed, pocked roads or pay an Uber tax to have another person tote me around. Public transport in Chicago is basically abysmal. I will take it from the airport during rush hour, but since Covid it’s gotten horrible.
I see an old acquaintance yell from the rooftops that “Illinois is open for business,” but all the job opportunities are with the state government. They don’t see the irony.
This chart may be all you need to know about opportunity in Chicago. This is the city's startup sector. A pittance. They do that much in a couple of weeks in the Bay Area.
No money means no growth. No growth means no opportunity, except, of course, if you want a state government job. Illinois is not open for business. Business is leaving Illinois as fast as it can.
I never “got” Vegas until I was at the Joe Brown Lunch listening to the president of the Liberace Museum give a presentation. He said something that resonated with me. “I needed to get the museum in the black. It had to earn.” That goes to the core of Las Vegas.
If it doesn’t earn or isn’t explicitly useful, they get rid of it. There are no sacred cows.
Chicago is the opposite, and the discussion over the Cortland Street bridge is exactly what you need to understand about Chicago and why it is circling the drain both financially and civically. A friend who escaped but goes back often said when they are there they feel like a “bored ape at the zoo.”
My kids went to Francis Parker School in Chicago. One of the school's mottos is “everything to help, nothing to hinder”. The city of Chicago’s motto should be “everything to hinder, nothing to help”. Especially true of infrastructure or capitalistic enterprises.
If you understand the city’s geography, the Chicago River runs through Chicago. The main touristy part is essentially a couple of islands. The canal on this map was dug back in the 1800s. Mostly by Irish immigrants.
Bridges are important because you cannot get places without them. Mayor Daley replaced the North Avenue bridge, and it looks great. It was done as fast as it could be done. He was corrupt, but got stuff done.
If you know Chicago, this bridge connects Lincoln Park to Bucktown.
Here is a photo of the Cortland Street bridge.
It’s just a rusty old expansion bridge.
It’s going to be closed for years. In Vegas, they’d blow it up. They’d have a fireworks display and sell tickets. A new glittery bridge would be built with a flamingo on it and a photo of Elvis. It would take a year if it impeded commerce—two years if not.
In Chicago, the bridge is going through committees. The bridge is landmarked for goodness ' sake… as if it were designed by Louis Sullivan or something. It wasn’t. It’s just old.
My acquaintance Stu Loren has been tweeting about it. He and his son are now doing a tour of the United States’ landmarked bridges. They have done the Golden Gate in San Francisco and the Cortland Street bridge in Chicago. Brooklyn Bridge in NYC next!
As Stu said, tear it down. Or, if it is so significant, build a new bridge next to it. Build a four-lane, two-bike-lane bridge. Save the steel and make an art exhibition.
When you read some of the comments on social media, it’s astounding how silly people are. “We don’t need cars.” Right, because you will bike your toddler to day care, bundling them up in the Burly during January. Or, you will send your kid to soccer practice to the Bucktown field from Lincoln Park, but you won’t have to drive because you will just Uber them there while you stay home and sip chardonnay with the neighbors. After all, you can track them on your phone so nothing bad will happen.
Communists aren’t there to make life better for citizens. They make it worse, and even worse than that, they figure out the economic incentives that inspire and motivate people to do things and take them away. That’s Illinois and Chicago government.
Chicago is no longer “the city that works”. It’s the city that taxes everything. It’s the city that is stupid. It’s the city of passing the buck. It’s the city of irresponsibility. It’s the city of nothingness.
It’s the city where if you criticize anything, you get the pleasure of experiencing a Maoist social struggle session.
There is no there there anymore in Chicago. It’s not relevant. The city’s mayor, Brandon Johnson, is such an inept communist that he lets Mamdani and LA mayor Karen Bass steal his headlines.






I escaped The Chi in 2019, happy to be gone but I return several times a year to visit family and friends.
Have you seen the overpass and off-ramps on the Edens Expressway at Old Orchard road?
I believe that they are now in year 4 of this project…
Sad story about a once great city. Socialists and Communists ruin everything they touch!