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Kass News: Why Steve the Pilot left Chicago. Sound familiar?

Anatomy of MY Departure

“Vote like your life depends on it, because it does.”

by Steve, the Pilot

February 19, 2023

Since my fishing buddy John (AKA Johnny Two Rods) is recovering, I wanted to do something for him but I didn’t want to send flowers. He’s no doubt now restricted from eating a Bari Brother’s Sub or a Giardiniera Italian Beef from Al’s #1 on Taylor St. but maybe a day off from putting out a column would be a nice gift. He’s often said to me, “I want your story. So here goes…

The Background:

I am the 4th generation of my family to live in Chicago. My dad grew up in Uptown and my mom on Alta Vista Terrace, before that area was called Wrigleyville. My mom’s side got pushed out of the old Greektown when Richard J. wanted Circle Campus and a highway, the other side was pushed out of Turkey when Ataturk didn’t want them there, so I guess I have refugee or Displaced Person (DP) in my blood.

I have two quips I’ve often used to tell my story.

Everyone in my family is here, either above or below ground.

I’ve been everywhere but nowhere (I’m a pilot and I lived 2 blocks from where I was born).

I grew up on the Northside, graduated from Lane Tech (when it was Technical) and only lived outside the city to go to college and serve in the US Air Force. I was the only member of a large extended family to stay and raise my kids in the city, everyone else had moved out to the suburbs. If you talk to any of my friends from college, the Air Force or my job, I was “Mr. Chicago” and I expected to die (of natural causes) in the city where I was born.

We learned “The Chicago Way” at a young age. One election my dad (who worked 2 jobs his entire life) decided he was going to vote in the Republican Primary. If you recall back in the day, we used 55 gallon drums for garbage cans. Shortly after the election our garbage cans disappeared but not our neighbors. Luckily one of my dad’s jobs was at a chemical company so he had access to an infinite number of empty 55 gallon drums. He would bring new ones and then again, only ours would disappear. Finally we stored them in the garage until the garbage men came, then put them right back in. The next election he voted in the Democratic Primary and it was no longer an issue.

The Long Haul:

After the Air Force I moved back, got married, had 2 kids and started my new life of flying. I didn’t have to live in Chicago, I wanted to live in Chicago. We were fortunate, both my wife (she worked downtown) and I enjoyed our jobs and we made a great living. So as the time approached for the kids to start school the questions started, city or suburbs.

First off, my kids are not an experiment, they get one try through life. We took a good look at the CPS offering, the selective schools and the system as a whole. There was a lot of risk, too much for my children’s education. We looked at the private system as well and felt comfortable with some of what we saw, we then asked ourselves the question… time vs money? The commute time to/from work would be substantially less in the city but the cost to live would be higher. You can make more money, you can’t make more time, so we stayed!

I had the most flexibility in my schedule, so I was the most involved in the kids’ schools, their activities and the community. I was a condo board president of our 400+ unit building, an election judge for 20 years, worked at the Green City Farmer’s Market in Lincoln Park and was a Boy Scout Leader. I voted in every election with the exception of one, during my time as an eligible resident.

I was around so much, there was one young lady who would see me in the neighborhood, as an election judge and at the farmer’s market. Finally, one day while I was working for a farmer friend of mine at the market, she asked if I was a farmer too. I laughed and told her no, that I was just helping out a friend but if she saw me coming out of the cockpit on a flight not to be worried because that was my actual job.

The 90’s and 00’s were good in Chicago. Richard M. shined it up, planted flowers, lots of flowers and crime was down. What most didn’t realize was that he was cleaning it up by washing away the city’s foundation. It started with the so-called wrought iron (aluminum) fences around every park, and capped off with the parking meter scandal and so many flowers in between.

Rahm cleaned up nothing, exposed none of the corruption and I would say his time is encapsulated in my sons’ minds with the following situation. We went to City Hall to complete a requirement for their Citizenship in the Community Merit Badge. As we got off the elevator there was a crowd, it restricted our ability to check in for the city council meeting the boys were supposed to observe. We were standing in the elevator bank area and the chanting began, “16 shots and a coverup!”. They learned A LOT about citizenship in the community that day.

The kids went to college, the wife retired and our life of travel was beginning. I mentioned I had missed one election earlier. The only one I missed (no, I even voted when deployed for Desert Storm) was the municipal election of 2019, we were overseas before voting started and did not come back until a few days after it had taken place. I voted in the runoff and happily voted for Lightfoot looking for that change… and boy did I get it.

The Decision:

We’ve been going down to Southwest Florida for 20+ years on vacation and loved the area but never had any intention of moving there full time. I was a Chicago Boy! but Covid, George Floyd riots, crime and budgets changed everything.

Let’s start with Covid. They locked down the city but you could still go get your booze, pot and gamble, though not go to church… huh? We went to a drive-thru, in-car, “actually peaceful” protest waving American Flags to stand up against all the closings and the Tribune reporter called us Nazis… huh? We walked through Lincoln Park on a beautiful May day, the sun is shining and it’s packed with people picnicking, playing sports, etc. but as we tried to walk over the bridge to the lakefront, the cop is telling us to turn around, the beach is closed… huh?

The state of Georgia had opened up, so we decided to take a vacation there for a week to get out from under the tyranny of Lightfoot and Pritzker, it was eye opening. Then the riots came to Chicago.

I had many friends from high school who went on the job. The story I heard was that CPD leadership went to Lightfoot’s office with a plan to protect us, as city after city started having riots. She told them we’re not doing that plan, all the guys I know have now retired. I rode my bike to the river near Wolf Point the morning after the first riots. I have pictures of smashed windows, looted stores and an iconic photo of all the bridges up, which I wish I never had the opportunity to take. I was devastated.

The second set of looting happened much closer to home, during that so called “Summer of Love”. Friends who have places of business, not even near downtown, were on their roofs and in their stores armed and ready, since the police wouldn’t or rather were told couldn’t. That morning after, the looting was still unraveling. I was at the airport going to work in my uniform and as I watched the reporting on the TV in the terminal, I started to tear up. While I think I hid it well, I wept for my city. My dream of living in Chicago until the end was over, I knew we were going to be moving. Lightfoot had destroyed our city in under 2 years.

My time in Chicago started in the tumultuous 60’s, the grimy 70’s and then the upward trend until we peaked in the 00’s. Those are many decades, it took a long time to build the city up. The taxes were lower, the city had less debt but it still took 30+ years and a lot of corruption tax to get it shiny. It is now completely bankrupt (anyone who tells you otherwise doesn’t know what 2 plus 2 equals). The taxes (property, sales, internet/phone, water…) are sky high and the infrastructure is collapsing. It took 10+ years for the Jane Byrne and that lakefront bike bridge to be built and the schools, oh the schools.

Imagine if you were 11 or older on the west or south side when Covid hit. No in person classes, no education for 2+ years. They’re 14+ now… do you think those kids went back to class? Most are lost for good with no future for them, the west or south side and eventually, the rest of us. CPS receives for each student, just as much as we paid for our kids to go to a top private school. Where does all that money go?

They started burning Michigan Avenue and now there’s a lot of boarded up storefronts and no one after dark. Carjackings, murders, robberies, shoplifting and mayhem in broad daylight, even in good neighborhoods. My family didn’t want to come into the city to visit us for fear of robbery or worse! The engine is dying and I don’t see it running smooth, if ever, for a very long time. They talk about investing in the neighborhoods, but without a well running engine at the core, the car doesn’t go. It’s pretty simple.

I was there when Chicago was down, I grew up through the tumult. I know even if the city does turn itself around, it’s a long road and I will be too old when it happens to enjoy it.

A story I told John kind of encapsulates the whole issue. I went into an Apple store down here in Florida shortly after we moved. As I jaunted out into the sunny blue skies with my purchase, I realized it was the first time I ever walked out of an Apple store without my head on a swivel worried about getting mugged.

It saddens me, but the back is turned, the decision has been made and there’s no turning around. I guess in a way, I’m now a DP, it comes full circle.

That’s the Anatomy of MY Departure.

Vote like your life depends on it, because it does.



Steve the Pilot was born in Chicago and lived on the North Side before being driven out of the city of Chicago.

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