Matt Rosenberg engaged in an in-depth interview with Richard Helppie on his “Common Bridge” interview show. Matt explained how progressive governance has produced such awful results for Chicagoans and emphasizes Chicago is still worth fighting for: “…you see the vibrancy everywhere. I walk sometimes 10 or 14 miles in a day, across Chicago, many of my friends think I’m insane. They’re all asking me, are you carrying? I love this place. I love the music, the architecture, the intellectual firepower, the neighborhoods; it’s still a fantastic city. So that’s why many of us still fight to try and get better policies enacted.”
Read more from Wirepoints:
- The CTA ran near-empty trains and buses during the pandemic – and it’s still struggling to fill them. Now it wants higher taxes on Chicagoans to pay for that mismanagement.
- Electronic monitoring horror show grows as lawmakers skate past SAFE-T reforms
- Poor communities bear the brunt of crime unleashed by Cook County bail reform and the SAFE-T Act: New Manhattan Institute report
- Chicago’s progressive agenda has been destructive for black communities

Expect no retraction or apology. This what they do.
The state’s existing buyout program for its own pensions is the precedent for Chicago, which should be a warning: Look out for similar exaggerated claims and shoddy analysis.
Matt moved from Chicago for Seattle many years ago. Recently he moved back to Chicago. Seattle deteriorated real fast in about two years. I know, because I live in Washington State. I am from Chicago. It’s interesting that Matt doesn’t say anything in his book how bad Seattle was getting or if that was a reason he left. But I can’t help but think that Matt’s positivity about Chicago relates to the significant rapid decline of Seattle. Seattle worsened even faster than Chicago, so maybe he missed Chicago and in comparison he sees Chicago in positive light. “There’s no place… Read more »
Despite its problems and it’s major role in modeling modern urban anarchy – which I detail here: https://www.newenglishreview.org/articles/the-source-code-of-modern-day-american-anarchy-was-written-in-seattle/?print=print – Seattle is still a place I am happy to return to in the summers. Except for the no-go downtown; and slightly improved but still feckless politics – it remains a beautiful place to stay. Police response has severely degraded in Seattle and as in Chicago it’s for a myriad of reasons. But while predatory criminality is common in Chicago it is much less so in Seattle. The people of Chicago – the law-abiding ones – are much warmer and more open.
Urban decay comes at you quickly ask those in Detroit and St Louis.
De-gentrification will be a popular word throughout the 2020’s. It’s already happening in Chicago as according to Redfin, neighborhoods bordering crime infested areas of the city are starting to drop – Bucktown is down -5.3% YOY, the West Loop is down -1.4% YOY, residents can’t flee the South Loop fast enough – down -5.7% YOY, Ukranian Village down -2.4% YOY. There’s a handful of other areas that are up low single digits – which is less than inflation, so it’s really a loss, like the Near West Side at +2.8% YOY, West Town +3.6% (it seems like inventory has EXPLODED,… Read more »
Meanwhile, Northbrook is up 25.1% YOY, Glencoe is up 19.1% YOY, Tinley Park is up 11.1% YOY, Hinsdale up 63.5% YOY, Schaumburg up 19.4% YOY, ST. Charles up 5.5% YOY. They former Chicago residents are moving to the suburbs and bringing their bad voting habits with them.
“Was” is the correct verb. Detroit was a fantastic city too.
It once had the highest per capita income in the US, also the highest rate in the US of home ownership. If Detroit had been an independent country c. 1940’s – 50’s, it would have been the fourth – largest economy in the world. That wealth built temples of art, theater, culture, civic life… now all fallen to ruin…
Spot on GM. The most underreported feature of Detroit in the 40s was its industrial base. They were able to convert auto production to war production quickly. WW2 was won as much in Detroit as by our soldiers. If the US gets in a war with a major power (think China) the whole country is gonna miss Detroit as our production has been shipped there by short sighted pols on the take (think the Bidens,Feinstein, etc.) The list is very long and has been growing for decades. I expect to live long enough to see America pay in blood for… Read more »
I have not lived in Chicago for a long time, but I still visit family and friends in the area on a regular basis. I see so much potential. Unfortunately I see even more self centered politicians who have know idea what an honest day’s work is. Its a pity such a wonderful place is run by such dunderheads!
Highly commendable , Matt, for sticking up for Chicago. It is heartbreaking to see what has evolved the last twenty years. It ought to be worth fighting for, but the citizens–i.e., the voters– are doing it to themselves. And if the people aren’t great, the city won’t be either.
Those that claim Chicago is a great city in 2022 clearly don’t travel and explore other cities.
Was Chicago a great city in the 1950s? Absolutely. Even as recently as the early to mid 2000s it was a great city.
You can not say with a straight honest face that Chicago is a great city today. Not with the level of bloodshed, rotting society, corrupt inept government, failing schools, failing infrastructure, declining healthcare & quality of life.
Skyscrapers DO NOT make a city great. The people, culture and quality of life do.
Not being from Chicagoland I disagree with the great opinions regarding it as a great city. To me the only thing good about it is that it is a magnet for keeping a certain element from moving to my area…no more no less
His friends think he is insane because he is. This will not end well for him. Like playing Russian Roulette every day.
I’ve never thought of Chicago as being a great city, but it was my city. I’m a product of the Chicago Public School system. Until recently, I lived my life in the city and its suburbs. I rooted for it to succeed for many, many years. I slowly came to the conclusion that failure was inevitable, and its residents far too foolish to save themselves. Unlike myself, Matt still hasn’t given up. That sort of makes me feel sad for him.