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Eight American Cities in Eight Days: Some Observations

My son, Nicolas, loved climbing rocks in Central Park. My wife and I loved that it was an easily accessible respite from the city.

This year for Spring Break, my family and I drove 2,200 miles from Chicago to visit family in Boston and New York City. Along the way we stopped in Cleveland, Harrisburg, New Haven and New Bedford, Massachusetts and spent the night in Buffalo and Pittsburgh. Visiting eight cities in eight days was an amazing opportunity to not only see how varied America really is, but also learn a bit about what cities are doing right and wrong.

Here, in no particular order, are some of my observations from our trip.

1. Boston and NYC’s rapid transit has a much tighter grid, and seems to be much busier than Chicago’s, but Chicago’s system is cleaner, quieter and a better riding experience.

2. Every city, no matter what the size, has some kind of cool thing other cities should all be jealous of. For Cleveland, it’s the West Side Market. Buffalo, it’s the stellar downtown architecture. New Haven, it’s an Italian community with a genuinely unique and excellent native pizza (and Yale too, I guess). Harrisburg, a terrific minor league ballpark right on the river. Pittsburgh, it’s a tight, bustling downtown with a vibrant restaurant scene that is unusual for many mid-sized cities.

3. The American landscape, is varied and beautiful. Just between Chicago, Boston and New York, we saw five very different landscapes that took our breaths away. The spaces between our cities are magnificent.

4. Rush hour traffic in Boston and NYC is horrific. I will never complain about Chicago traffic again.

5. Most everything in NYC, especially Manhattan, is obscenely expensive. I can’t understand how any kind of middle class can possibly exist in Manhattan and most of Brooklyn. This is not a good development for the city.

6. Seafood on the East Coast is plentiful and relatively inexpensive. I’d forgotten this fact, even though I lived on the East Coast for twelve years. I miss it.

Buffalo’s City Hall. Completed in 1931, it is an art deco masterpiece covered with friezes.

7. We only spent a night and a rainy morning in Buffalo. I’d like to spend more time there. The city is absurdly inexpensive, and we stayed in a great hotel and had a spectacular meal at a French restaurant downtown. Maybe we hit the best parts, but I sense there’s more to the city.

8. Boston’s new Seaport district is a development triumph, but a failure of city planning, in my opinion. We visited the Institute of Contemporary Art (not worth a return, I think) and explored the Seaport area a bit. It is full of glassy buildings, trendy young people and pricey-looking restaurants. I suppose this is appealing to corporations and twenty-somethings looking to burn inflated salaries, but it lacks soul. I wonder how popular it will be in twenty years.

Me enjoying Franco Pepe’s white pizza, which covered with clams and garlic and with a crispy crust, was probably the best pizza I’ve ever had. Better than in Chicago. No lie.

9. Now that I’ve had New Haven-style pizza, I think it’s better than Chicago-style and Brooklyn-style. I know this is sacrilegious for me to say, considering my Chicago roots, but facts are facts. Get to Franco Pepe’s Apizza as soon as you can.

10. Coney Island is wonderful. It’s a good thing Chicago doesn’t have an amusement park I can get to by L, because if I lived in NYC, I’d hit Coney Island’s roller coasters at least once a month. So great.

11. We visited downtowns of Buffalo, Boston, Harrisburg, New Haven, New York and Pittsburgh. It doesn’t take much observation to see how dense downtowns – and really entire cities – are able to offer many more amenities. Buffalo and New Haven’s downtowns have large amounts of empty space, but Boston and Pittsburgh have downtowns hemmed in by either water or neighborhoods, enforcing density (NYC is a whole other category). These dense areas create virtuous circles of culture and commerce in ways obvious to any observer. I can’t understand why so many Americans fear density. It makes more things possible.

12. I lived in Harrisburg for three months in 1996 and hated it. Visiting last week for the first time since then, I was happy to see that it has improved somewhat, especially the historic neighborhood just north of the Capitol between Front and Third Streets. The city still has a long way to go, but I would no longer call it a “dump”, as I did twenty years ago.

Downtown Pittsburgh is dense, busy and vibrant, even on Easter weekend, when we visited.

13. We did not have much time to explore Pittsburgh, but the downtown has visibly improved since I last visited fifteen years ago. Most of the empty lots have been in-filled, there’s a real restaurant scene, and on Easter Sunday, there were plenty of people wandering around a downtown that lacks residential buildings, which suggests to me that people find downtown worth driving to hang out.

14. Most on-the-road fast food is total garbage. I’ve come to adore Culver’s in the Midwest, and man, it’s a great go-to when you’re just looking for an O.K. lunch on the road. Also: Why the heck do so many toll road service plazas have Sbarro? It is so unbelievably bad.

15. American interstates are incredible. I drove from Paris to Madrid in 2002 and was stunned at how poor the roads in both France and Spain were – sometimes they were barely better than gravel with tiny signs you could miss in a blink. American interstates on the other hand are pristine, have excellent signage and easy to use on/off ramps. We Americans spend an incredible amount of money on our highways, an amazing subsidy for trucking and citizens with enough time and money to use the roads for long distance travel.

The Cleveland West Side Market. Jammed with real vendors in a beautiful building.

16. Cleveland’s West Side Market is amazing. Noticing it on the map while driving through the city on I-90, we decided to get off the interstate to check it out and we couldn’t have made a better decision. This is not a tourist market – stocked with working butchers, bakers, fish sellers and produce stands, it is the kind of place regular people could go shopping on a regular basis. Oh! And the building is gorgeous. Every American city needs places like these. Shopping becomes a social experience and you get to meet the people who care about bringing you great food.

17. Boston is crawling with university students. While the city residential population is about 685,000, the city reported 152,000 students from its 35 colleges, universities, and community colleges in 2010. From past experience, I’ve noticed that Boston during the summer break has a completely different vibe than during the school year – it’s like the city is quieter and more relaxed.

18. I haven’t mentioned New Bedford’s incredible working harbor, the super cool Fraunces Tavern in Manhattan’s Battery, Boston’s North End, Buffalo’s great Pierce-Arrow Transportation Museum, Central Park, the tire shop in The Bronx that fixed a flat for $12 and so much more.

Finally, if you have an opportunity to take an American driving trip like ours, I strongly recommend it. You’ll see so many great things.

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Five Reasons Chicago’s Coming Election Will Indicate America’s Future

Chicago mayoral candidates Lori Lightfoot and Toni Preckwinkle. Credit: Mike Fourcher and WBEZ

Unless you’re a local, American mayoral elections can seem provincial and quaint. “How could a contest for chief garbage collector and town booster be important to the rest of America?” we ask.

But Chicago, preparing for a groundbreaking city election on Tuesday, is a true bellwether city for urban America, and much more conservative than decades of Democratic Party control lets on. Tuesday’s runoff election for mayor and city treasurer, and final contest for many City Council seats, will reveal a great deal of insight on what urban residents, now 80% of America, will be prioritizing in the coming years. While city dwellers set the pace for American politics, Chicago’s Midwestern values hew more to the middle than coastal Los Angeles and New York City, providing a better prediction of what’s to come on the national stage.

Since the start of Chicago’s runoff campaign five weeks ago, polling has pointed to a mayoral victory by rookie politician Lori Lightfoot. Yet, the mayoral runoff has been mostly about style, rather than policy substance, since Lightfoot and her opponent, Cook County Board President Toni Preckwinkle, have very similar liberal outlooks on policing, housing, taxation–and just about everything.

Meanwhile, polling for many for City Council runoffs has been favoring lefty, progressive candidates seeking to sweep out old guard pols, making it unlikely that the last few “machine” aldermen will be able to keep the reins of power away from a new, progressive mayor. On top of that, Chicago is about to elect for the first time a city treasurer who was not pulled into office by mayoral coattails, resulting in a new city-wide office held by someone with their own, independent electorate.

Once the ballots are counted, Chicago will see a whole lot of change Wednesday morning. There are five major reasons why all of America should pay attention.

1. Race and minority status have been election issues in brand new ways. Both Toni Preckwinkle and Lori Lightfoot are African-American women, a first for Chicago in the mayor’s office, no matter which is elected. And Lightfoot is married and openly gay with a daughter, another big first for Chicago, if she is elected. Yet, because both candidates are black women, minority status has not been a divisive campaign issue, but instead repeatedly affirmed as a gain for Chicago.

This is a remarkable development for a city that has lost 181,000 African-Americans in the last eight years, and one that has struggled with “a tale of two cities” with crime and economic underdevelopment raging in minority communities, while white Chicago has been booming in every way imaginable. A black, woman mayor with working-class roots (Preckwinkle’s father was a letter carrier in Minneapolis and Lightfoot’s was a steelworker in Ohio) will be a radical change from the white, professional class mayors Chicago has had since 1989.

Under Lightfoot or Preckwinkle, perhaps the project of racial reconciliation and equitable neighborhood development begun by Chicago’s first African American mayor, Harold Washington, and halted by his untimely death in office in 1987, can be restarted. All signs seem to suggest that Chicago voters are ready for it.

Unlike Chicago’s other recently famous black politician, Barack Obama, both Preckwinkle and Lightfoot have a history of speaking plainly about race and the role it plays in policymaking. Also, both candidates have demonstrated an awareness of how white, Latino, black and Asian perspectives differ, and how personal racial transgressions can feel. With its new leadership, Chicago will be positioned to be a model for post-Donald Trump racial reconciliation.

2. Chicago’s coming crime and policing policies will worth watching. As I mentioned before, Chicago is much more conservative than its Democratic voting record suggests. One leading “moderate” candidate for mayor eliminated in the general election, Illinois Comptroller Susana Mendoza, was nicknamed “Electric Suzy” when she was a state legislator, because of her strong support for the death penalty. As a 2019 mayoral candidate, Mendoza attracted campaign staff from outgoing Mayor Rahm Emanuel’s team, and made “get tough on crime” policies a major plank of her campaign.

In contrast, both Lightfoot and Preckwinkle are strong proponents of police reform, and each of them played a role in pushing Chicago towards the consent decree it is now under that will make major changes in how the police department operates. This is a big departure from Mayor Emanuel (and his predecessor Richard M. Daley) and from many other leading mayor candidates eliminated in the first round of voting. Long before Laquan McDonald was killed by a Chicago police officer in 2014, views on policing had been a dividing line between white and minority communities, with Emanuel and Daley resisting major policy changes.

Despite President Donald Trump’s promotion of 1980’s-era police tactics, urban America is calling for change. Preckwinkle’ leadership on eliminating cash bail, and Lightfoot’s recognition as principal author of the 2016 Chicago Police Accountability Report stating that the Chicago police department struggles with racism, suggests that Chicago is preparing to address crime and race in ways America’s federal government has been avoiding.

3. Chicago policymaking is about to get much more progressive. There was an incredible moment in one of the many televised debates between Lightfoot and Preckwinkle, where they argued over which one would be a more aggressive proponent of affordable housing and moving resources to underdeveloped communities. After eight years of Emanuel’s New Democrat, pro-business policies, where the Chicago Housing Authority sat on hundreds of millions of dollars while the city endured a low-income housing crisis, it was revolutionary to hear an argument about who would build houses faster. Both mayor candidates have promised liberal-friendly changes to city school governance, policing, neighborhood development and cannabis law, all areas where Emanuel has exhibited feet of clay.

While nationally, urban America is having a left-wing moment, Chicago’s incoming leadership will be liberal enough to make big changes but yet challenged to move a big city bureaucracy that naturally resists lefty impulses. Like much of America, Chicago will resist quick fixes and illustrate how hard it will be to implement a progressive agenda.

4. Downtown big business won’t be the first priority. Elected in 1989, Mayor Richard M. Daley put a top priority on building up Chicago’s downtown and pushing it to diversify into more finance and national corporate headquarters, as many other Rust Belt cities’ downtowns withered throughout the 1990’s. Emanuel, Daley’s successor in 2007, put the downtown-first policy on steroids, pouring resources on while doing everything he could to draw corporate headquarters to the Loop. Emanuel’s downtown focus has been hugely successful, as Crain’s Chicago Business recently reported that since 2010, the Loop added 130,000 new jobs.

But this boom has been mostly to the benefit of professionals, who are mostly white, as high wage industrial jobs working class blacks and Latinos relied on dried up. During the same time black neighborhoods have emptied out, and large parts of the South and West Sides have been locked into a cycle of disinvestment and high-unemployment since the 1960’s. Preckwinkle and Lightfoot have both made neighborhood investment top planks of their campaigns. While it’s possible for neighborhood investment to not be anti-business, many of Chicago’s business leaders are concerned about what they hear from the mayor candidates, expecting rent control, higher commercial property taxes, and less support for big downtown projects.

Like the rest of America, Chicago’s neighborhoods need infrastructure and private investment to spur growth. The 21st Century manufacturing and knowledge economies still need to take hold in Chicago and the city’s next mayor will have to write a playbook most of America has yet to discover.

5. The end of mayoral autocracy and a more activist City Council is coming. Chicago’s fifty alderman have long quailed under the gaze of their mayor, but come Wednesday, more independent-minded aldermen will hold office than ever before, with the vast majority of alderman elected to office without significant help from the mayoral candidates – a big change from past elections. Past mayors have held power by allying with aldermen who ignored city-wide issues in return for dominance over their home wards and help from the mayor around election time. But this year’s Council will bring a majority of aldermen with a history of asking unpleasant questions, and too few of “old machine” pols to keep the levers of power away from activist Council members.

We should expect a bumpy ride for the new Chicago mayor, as City Council pushes back in ways it hasn’t done since the early 1980’s. But unlike those days’ Council Wars between a progressive African-American mayor and reactionary white aldermen, Chicago’s next Council session is likely to be pulled between independent-minded aldermen that are more left than the mayor, and reactionary whites and minorities who are more conservative on policing and/or taxation than the mayor. As it stands today, it is unclear what kind of legislative coalition a new mayor will be able to assemble, and that suggests conflict is on the horizon.

America’s Democratic Party wrestling match between lefty populists and centrist establishment-types is about to be played out in Chicago. What happens here could be a good indicator of how hard it will be to establish a coalition if a Democratic president ascends to the White House in 2020.

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After A Visit To New York, Some Reflections On American Cities

Second Ave. and 60th St in New York City, taken by me from the Roosevelt Island Tram, which floats above the street.

I visited New York City this weekend to visit my sister and a few friends. I’m trying to visit more of my friends and family that live in other cities, to broaden my experience beyond Chicago. Besides New York, this year I’ve visited friends and family in Milwaukee, Boston, Cincinnati and Lexington, Kentucky. After five years of not much travel beyond the usual family vacations, it’s been a good opportunity to see how other parts of the United States work.

When I visit a city, for the first time or fiftieth, I try to walk as much as I can, take public transit and if possible, do things that regular residents might do: grocery shop, see a doctor, eat lunch at a joint frequented by office drones (of which I am one). I find the regular things are much more revealing of a city’s character than anything else. Where does a city put its energy? What is the struggle or joy of being a resident?

So, here are, in no particular order, some observations about American life in some big and small cities I’ve visited this year.

  1. New York’s density makes it vast, and difficult to traverse. Moving from borough to borough takes concentrated effort. I love the subway system, but to go five miles from Manhattan’s Upper East Side to downtown Brooklyn took me forty-five minutes. I don’t know how that can be improved, but negotiating closed subway lines, transfers, etc. was hard, even for an experienced traveler like me.
  2. Although it has so much to offer many cities don’t, just doing the basics in NYC can be grinding. At one point it took me 20 minutes to refill my MetroTransit card (the story isn’t worth it). Going grocery shopping in Manhattan requires a dedicated trip and once you’re in the store, you’re faced with much smaller pickings than other cities and much higher prices. Every friend I visited with had a harrowing commuting story. That kind of stuff could wear you down.
  3. Beyond America’s biggest Northern cities like New York, Boston and Chicago, it’s hard to live without a car. I know there are people who do it, but most American cities are just not designed for life without a car. I know many Americans like their cars, but that’s a huge sunk cost, and will keep us from enjoying the benefits of density.
  4. I’ve visited Boston maybe fifty times in my life since I have family in Massachusetts and I went to college nearby. This spring, I tried using BlueBike, one of the bikeshare services in the city. It was a revelation. Going from West End to Fenway, with a few stops in between was easy, and cheap as heck, since I had bought a $10 day pass. Easier than taking the T and a ton of fun, since I got to see much more of the city than I would have if I were underground. I didn’t get a chance to use Citibike in NYC this time around, but I saw I ton of people using it in Manhattan and downtown Brooklyn. Total game changer for getting around in a big, dense city.
  5. New York’s subway system is really incredible. While you expect it to move you around the city easily, you don’t really appreciate how special it is until you’re three stories down, walking to transfer from one line to another, and you come across a vast underground mall lit by a skylight four stories up. It has been upgraded and improved so that it’s more than just transit, it’s an experience. I haven’t ridden the subway in Los Angeles, but Boston, Philadelphia, D.C. and Chicago’s subways are certainly not this nice. I wonder if every city had subways as clean and convenient as New York’s, would more people use them?
  6. The culture of “Internet Delivery Everything” has taken New York, Chicago, Los Angeles and San Francisco by storm. But the rest of the U.S., especially medium-sized cities like Milwaukee and Lexington, is experiencing this economic-phenomenon in fits and starts. Amazon delivery is everywhere, but not necessarily Uber Eats, Grubhub, grocery delivery services, and especially good Uber/Lyft coverage. These services have transformed my life in Chicago, freeing up hours of time a week and changing the way I think about shopping and getting around. When I travel to cities without these services, I realize how much I depend on them, and how I really don’t want to be in a place without them. I’m not confident delivery services will eventually get to every small and medium-sized American city, largely because of a lack of density. I imagine this will become a major drawback for those used to big-city life and make it hard for smaller cities to compete.
  7. With the exception of the biggest, many Northern cities are experiencing a hollowing-out, with big population drops and significant downtown vacancies. The big test for any city is – how busy is the downtown after 5:00 p.m.? But visiting Cincinnati was an especially big shocker for me: Almost the whole western half of downtown, the part without Proctor & Gamble or Fifth/Third Bank headquarters, was virtually empty. While three blocks away the city was buzzing, whole city blocks on the west side were mainly occupied by pigeons. Like Cincinnati, big chunks of Milwaukee are vacant – as are parts of Chicago, which has lost 250,000 African-Americans in the last ten years. This is a crisis of epidemic proportions, and it worries me that it isn’t part of our national dialogue.
  8. Travelling around, it becomes hard to ignore that American cities are in serious competition with one another. The winners are ones able to demonstrate a specialized niche, like Pittsburg’s tech sector, Boston’s higher education offerings, New York’s everything. I seriously worry about the future of small and medium-sized Midwestern cities. Sure, Peoria is a nice place to live, but if Caterpillar were to leave, why would anyone move there? The biggest cities are sucking up talented young people (Chicago’s 60661 ZIP code has the most Millennials of any in the country, do you think they’re planning to move elsewhere?) and smaller cities don’t have a convincing story. This also seems like a burgeoning crisis we’re just not talking about enough.
  9. This last year I’ve been wowed by New York’s subways, Boston’s Big Dig, Cincinnati’s riverfront athletic complex, Louisville’s new Ohio River bridge. In each one, every detail has been attended to, every standard met. These infrastructure projects change the way we interact with cities and the way we think about what’s possible. America at its greatest, is when it changes what’s possible. We need more of these kinds of projects, because it will change what we think about ourselves.

I really need to visit more American cities more often. If you’ve got an air mattress, let me know, because I’d love to stop by and go for a long walk. Drop me a line!