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.

  1. Everyone in my family is here, either above or below ground.
  2. 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 and John fishing for steelhead on that great river up north.

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

Comments 69

  1. I lived in Chicago for 66 years. I moved in 2021 to a SW suburb. Have not regretted it. I want to take a drive downtown to see for myself how bad it is. Haven’t yet.
    Lightfoot destroyed the City in two years. It will take quadruple, if not more, to undo the damage she did.

    1. I love the City, miss the Theatre, miss shopping on Michigan Avenue, driving to a Bear Game. No more. Chicago is starting to look like old Detroit, the Governor and the Mayor only care for power and they have destroyed this once beautiful City. Wake up people take back the State and the City, throw out the thugs and the criminals PUT THEM in jail, hire more Police, and most important Vote for the right people to Win in our Schools and Library positions. I do not have young kids or grandchildren, but I love Chicago and America and as an immigrant it hurts me to see the Minority voices destroy everything we the immigrants that came here legally worked so hard to built. They could have joined us but decided they would rather take things from the people that worked so hard for free and stealing. PLEASE VOTE YOUR CHILDRENS AND GRANDCHILDREN’S FUTURE IS AT STAKE.

  2. Sad but all too familiar story of one being forced to leave the city we once loved…..I also fled the city for south Florida. We voted with our feet but many just don’t have that option… yes, vote like your life depends on it.

  3. Born in South Austin, spent early years in Heart of Chicago, and grew up, got married and started a family in Belmont-Central. Now, since September, became permanent Florida resident and living in our former “Snowbird” house year around. Still go back “Up North” for holidays and special occasions but feeling a lot more comfortable – read that as “safer” – here. Things change but never ever expected Chicago to corrode as badly as it has and it breaks my heart.

  4. Steve, the Pilot, you, sir, have a compellingly honest narrative voice! Great writing about the horrible condition of the city of my birth made my morning!

    Thank you!

    1. Sad but true. Last time I was in Chicago proper, I took my kids on a field trip to the Shakespeare Theater on Metra. That was in 2012. I no longer live in Illinois. I consider myself fortunate to be out of there.

  5. Boy, can I relate to the garbage cans disappearing for voting “the wrong way” reference. I grew up at 2726 North Nordica in the 36th Ward and it is so true! This essay says it all. Thank you, sir, for all your decades in Chicago and for being such a solid citizen. Enjoy the rest of your life in southwest FL. I may be your neighbor some day, but my kids are starting to have kids of their own and my wife will never leave them! John Kass, you have excellent friends!

  6. What an absolutely brilliant assessment of Chicago through the years. I was born, raised, and educated in the city, including college, and I could relate to everything you described; even the 55 gallon garbage cans from the precinct captain.
    I left my city and the state of Illinois in 77 but in my heart I have never left my roots. It grieves me to see what has become of my birthplace.

  7. This column sadly hits home. We live in the Chicago area for over 45 years and reluctantly left in 2020 for those exact reasons! We are enjoying lower taxes and a safe community here in Florida. I pray for that once great city and hope it can recover from Lightfoot’s destructive years.

  8. So heartbreaking. Wish this could be posted to every Chicago household before the upcoming election.

    We too live in a Chicago suburb and the crime is beginning to seep into the northwest suburbs. I feel so bad for the children who are growing up in this atmosphere. God help us all.

  9. Sadly, I don’t think voting will make the slightest bit of difference: Chicago mayors are anointed and, then, there is the County to deal with. That fact that you voted for Lori Lightfoot because you believed that you were voting for “change” tells me that you still don’t understand that. Congratulations on your move to Florida…just don’t do to Florida what has been done to Chicago.

    1. Daniel – you speak the truth. Lightfoot was an obvious radical grifter from the jump. You either know or you don’t. There are many that are awake and sadly many that are woke.

  10. Very well written, and very sad. I’m a retired Cop who worked with CPD my entire 36-year career and still have many CPD personnel as students in classes I teach.
    It is so sad to see how badly they have been maligned and slammed by the (sic) “media” and many elected (sic) “officials”. I have never seen CPD morale lower.

  11. Great article Steve!! We’re also from the once Great City of Chicago. Grew up, went to school (Gordon Tech, now DePaul Prep), worked there for 40 years, and imagined ourselves living there in retirement. I’m so glad we didn’t pull the trigger on purchasing in the museum complex. Like you, we’ve relocated to southwest Florida, and haven’t looked back. It saddens us though, that we can’t go back downtown to visit, for fear of being a victim of a crime. Changes are desperately needed, but with so many likeminded people leaving, my confidence is strained. I hope to see more articles from you!

  12. We, too, reluctantly shifted our legal residence to a place we owned in NE Florida in September 2020, six months into the Covid shut down, and it felt liberating, less because of the tax savings than the change in political environment – freedom vs. authoritarianism; the public/taxpayer interest prioritized over the demands of public employee unions; enforcement of criminal laws vs. the refusal to do so. The passage of such radical new laws as no cash bail and expanding collecting bargaining rights for the ultra-radical CTU (repealing the restrictions that I sponsored as a state senator in the mid-90’s) has sadly confirmed the wisdom of our move.

  13. Great story with a regrettably sad ending. I was born and raised in the city, mostly on the far southwest side, raised a family there, and served over 30 years with the CFD.

    In late 2013 I purchased a home in SW Fla. Over the years I spend more time there and feel almost completely safe (as when you exited the Apple store).

    We still do the “snowbird” thing as both of my children live in Mt. Greenwood and I have to admit their neighborhood is strong, but the threat looms large.

    You are so right about when the decay started and it is now almost complete as the pols rob and plunder at the expense of a civil society.

  14. So true and thank you, Steve. Ask yourself and others:

    Who is happy in Lori Lightfoot’s Chicago? Who is winning in Lori Lightfoot’s Chicago?

    The answer to both questions is no one. Even Lori Lightfoot is not happy. And hopefully not winning the election.

  15. This is very moving Steve. Your moving is a great loss to your neighborhood, the city, and the state. This honest description of the crippling effects of poor leadership and rampant corruption is devastating.

    The loss of good people, who have assets, who have institutional knowledge, who have heart, spirit, is even worse though. The city needs to be rebuilt. Who will rebuild it if salt of the earth types are gone? Who will lead us?

    The people are not racist. We had two black ladies in the runoff for Mayor. We elected a black, lesbian, leftist as Mayor who said she was going to fight for the marginalized and make Chicago work for ordinary people.

    What we got was a narcissistic, paranoid, posturing elite, who treats working people with even more contempt than Rahm Emmanuel. How could we have conned so. How can black pols like Lightfoot, Bobby Rush, Danny Davis, Obama, hurt black kids even more than the supposedly racist Daleys?

    What the hell did they do with all the Covid money? Mental health centers still closed, homeless people in the arks and at the airport. And Lightfoot says we are racist or homophobic for not voting for her?

    There’s a double speak and a sleight of hand going on un politics, in ur society right now. The government and the oligarchs who really own the country have conspired to divide and conquer us with race, identity, class, geography, religion, and big tech and the media are their weapon.

    Unless we can find common ground and treat each other with respect and dignity, these problems of division will continue to fester. Who disagrees with public safety, good schools, jobs, opportunity, taking care of the sick, elderly, needy? Virtually no one. Yet, race is used as a cudgel. Gender, LGBTQ, elitism, are used as a weapon to divide us. Who doesn’t have a gay person in their family, or extended circle? No one.

    We’ve got to come together. We don’t have to agree on everything, we don’t have to agree on most things. If we agree on freedom, peace, privacy and dignity, we can make things better.

    I’m so sorry you had to leave Steve. I wish you and your family the best.

    God help us.

    1. Great article, and even better reply. I’m a transplant to Chicago but have now been here for 35 years (minus a few for law school) and am ready to leave as soon as my kids are done with high school/college (only because I hate to put them through more than one major life change at a time). It’s hard for young adults to understand what’s become of our once-great city, even when I talk about it every day. Praying that Lightfoot loses big . . . but I also worry about Johnson winning a runoff against Vallas as he seems even more anti-progress “progressive” than Lightfoot, which is not an easy feat. God help us all!

  16. Thank you Steve for helping the Kass!
    My parents moved out of Chicago in the late 40’s and I always enjoyed going into Chitown to see the Cubs play ball or check out the museums. I have not set foot in any part of Chicago and never crossed that border line since 2002. Yes, I have missed several family celebrations, 50th wedding, new wedding, and other less happy scenes… regrets as people ask why and I tell them I plan on living longer and take care of my wife’s safety here in the burbs.
    I enjoy the closeness of our large family west of the line and since approaching 90, still have a bucket list that can be neatly filled without crossing that line east of me.
    God bless the citizens of Chicago remaining, but I understand that it is very costly to rent a U-Haul lately…..if any are available.
    God bless you and yours Steve and John, get well so that fishing rod does not rust….

  17. The details of my life are a bit different, but the story is much the same. I never wanted to leave my wonderful city, but in 2015, I saw the writing on the wall. My city was broke, and personal safety was in jeopardy as crime turned mobile. Bands of sociopaths with guns were starting to threaten every neighborhood. Rather than submitting to this nightmare, I began the painful severing of my roots. No longer do I worry about a carjacking, or a pistol in my face. My Chicago is gone, and is now only a sentimental memory.

  18. This is the story for so many of us. I grew up in Chicago, with the gritty city in my childhood, all the political circus following “the Boss’s” death, and the beautification by his son while everything rotted underneath. I practiced law there for 30+ years, 90% of that right there in the Daley Center. I could walk the Loop blindfolded. Then the “Progressives” came. I witnessed the riots, and called the CPD three times in an hour while they looted the Target store in my Streeterville apartment building, but no cops were there. I had enough. Now I live in South Carolina, along the coast. I don’t look over my shoulder every time I walk the dog before the sun comes up. I don’t see graffiti covering every square in of concrete. I don’t walk around homeless people on every corner.
    Yes, Chicago is done. Lightfoot put the final nail in the coffin. With Daley and Rahm, people might have stayed to help bail the place out. But that incompetent poser now up on the 5th floor made sure the city will now die.

  19. I do not live in Chicago. But Chicago is a second home. My step-mother lived and worked there for her entire life. When I got married and we had our daughter, my step-mom reveled in teaching us about the city. Every trip was like a tour. If we went to the zoo, we had to make a stop at RJ Grunts. Every Christmas we had breakfast at the Walnut Room before seeing Santa. She wanted our daughter to enjoy all the city had to offer, show her old haunts, and share her memories of the city she loved.

    Now, our daughter wants to move to the city because it reminds her of grandma and all the great times they had. Sadly, we are trying to dissuade her. The expenses are great and the crime is never ending. But she wants one year. Just one year to experience the city she feels a strong connection to before moving on.

    What politicians have done to Chicago for decades is criminal. And yet there will be no reckoning. Voting matters. But the choices for mayor are not stellar. Chicagoans deserve more than voting for the candidate who will do the least damage. They need someone who will actually have solutions. Make your choice wisely.

  20. I saw Chicago for the first time in May of 1964. I was barely four years old and visiting from the West Coast. I fell in love with the city. My Finnish grandparents met here before WWI and my mother lived on School Street while she attended kindergarten. Chicago just felt like home from that first visit. I didn’t get the opportunity to live here until I was thirty-eight and except for two years in San Francisco, have lived here ever since. I cannot imagine living anywhere else in the country. I’ve lived in Seattle, Portland, San Francisco, Los Angeles, Salt Lake City, small town Indiana, Northern Ohio, Boston, Madison, Wisconsin. No where else feel like home to me. I’ve thought about leaving but I just can’t do it. I have to stay. I love this city. I don’t think it’s too late for Chicago. Maybe I’m an optimistic fool. But at least I’m not a maniacal Progressive.

  21. Thanks for sharing your story Steve! Sadly, very much like so many I hear frequently who have moved into SW Florida from Illinois, New York, New Jersey, Massachussetts, Connecticut, and even California to escape! We left Madiganistan in 2015 and never looked back. There are some things I miss about the Chicago area, certain foods, restaurants, parks, etc., but it is all so changed now. That was made clear last summer when I was at McCormick Place for a business conference. It was scary walking to the Metra from a restaurant in the south loop with a friend, and I will never repeat that. Just the number of people riding the Metra trains was an indication of how weak the downtown economy was vs. my past regular work rides into the city from the NW Suburbs!
    In contrast, Florida is booming, there is freedom from the dictatorial, taxing and hypocritical elites out to take money for themselves, and we enjoy good law enforcement and government that mostly works for the people. It has it’s problems, like corruption here and there (nothing like Chicago’s), but such a better place to live! I doubt Chicago will ever revive to what it once was, as too many of the people who cared have left.

  22. Great column and thank you for writing it.

    We too fled to SW Florida, and we are happy we did. We initially planned to go back and forth, but that quickly changed in late March 2020. We bought our place here in February 2020, and when we got locked down, we soon drove down here and never looked back. We visit fairly often to see family and friends, but not downtown. Probably will never make it back down there, which is a shame.

    Chicago was a great city. It is no longer that.

  23. I relocated to Chicago proper in 1991, and lived there for almost thirty years. I had wanted to do so ever since I had seen, “The Untouchables.” Circumstances were such that I left only a couple of years before it all went to hell. I saw it coming, though.

    Richie “Shortshanks” Daley only looks like a reasonably decent mayor in comparison to The Dwarf, and now, Beetlejuice. Having worked more than a few elections as a volunteer Republican poll watcher, I knew how the corrupt Chicago and C(r)ook County machine worked. The city and county were corrupt enough by themselves, but I knew that the sh*t all flowed downhill from Springfield.

    As early as 2010, I had expressed my desire to get out of Illinois entirely to my now ex-wife, my rationale being that single-party rule eventually removes liberty either in an effort by the political class to preserve such for itself, or through mayhem and anarchy, with only the criminals and political class benefiting from the lawlessness.

    I had already lived under authoritarianism and was not about to do so, again. So what I saw happening in Chicago from my new, adopted home state of Texas saddened me deeply, but sadly, it wasn’t surprising.

    I feel for everyone who desperately wishes to leave, but cannot, for whatever reason.

  24. I too was born and raised in Chicago in the Back of the Yards. I thought it a great city and enjoyed taking the bus to Rainbow Beach and with lots of transfers to Riverview or even walking to the Colony or Marquette Theater for a movie with friends. I saved my bus money by walking to Vis and back almost every day, never worrying about being mugged, shot or kidnapped. It was safe and people looked out for kids in those days. After high school I got married and lived with my husband in his family’s 2-flat in Sherman Pk. until the day MLK was killed and we had tanks on our streets in response to cars being overturned/torched and violence erupting all over the city. We moved to Oak Lawn in 1969 and still live in the same house. I look at what I used to think the best city in the world in horror with crime of every kind running rampant…and no consequences. I also see crime spreading to suburbs in every direction and people actually curtailing their activities in response. Very few are willing to take the risks associated with going downtown, the lakefront or other venues that used to be popular, especially when considering expressway shootings that might take you out on the way home. These days I worry because my husband’s health is deteriorating and I’m going to be faced with living here alone. For the first time I have to admit that’s a scary thought. Last year a foreclosed home next door was purchased by a national rental company and a sketchy group moved in that was greeted one morning by armed-to-the-teeth, bullet-proof vested FBI and county law enforcement as we were having our morning coffee. After working with local govt. and police with constant updates on activities, they were finally put in jail and some evicted. It seems there is little to stop such happenings and I wonder how far out from Chicago people will have to move to escape all such chaos to raise a family in peace. Worse, we have a Federal govt. that is trying to change the world, cancel all we have held dear for decades including family, faith and education. If we don’t start electing better “leaders” even Florida won’t be far enough.

  25. It’s not just Chicago, but the entire state of Illinois. Schools state-wide are a disaster and all theat money is simply a racketeering scheme conjured up over the years by Democrats and greedy teacher unions. Public employee pensions are another wealth transfer scheme hatched by Democrats over the years and now the obligations are unimaginable to overcome. There’s very little going on in Illinois politics to right the ship. I threw in the towel and departed for Florida a couple years ago. There is simply no means of countering the Democratic super majorities and until voters have the guts to demand new politics, it will never change.

    1. Sad, but you are correct, Tim.

      We also left IL in the late 00’s. Just didn’t see any way that the ship could ever right itself, not when there are still people who find it amusing to say that they have the best politicians money can buy.

      They have very expensive politicians, but they’re not worth a plug nickel.

  26. Steve – I feel your sorry. I grew up in South Shore when we could walk to 71st Street to do all our shopping, banking, eating and ride the IC to the loop, or the “Jeffery 5” bus downtown. Spent 3 years in the Navy, and then in 1973, had to move my folks out their 2 flat to the north side, after a major robbery of their apartment. So, the journey to the north began. My wife and I moved to Lakeview, where our son now has a restaurant on Broadway, eventually we moved further north to Lincolnwood, along with my parents, where our kids went to school and high school. Downsized from Lincolnwood home in 2004 to condo in Glenview, yet, we’re both reluctant to journey back “into the city!” Our cop friends and/or relatives tell us to only go day time, and keep head on a swivel, and concealed carry when possible!!! Be aware of your surroundings at all times!! What a shame. Have warned my spouse I don’t know how much longer we’ll be able to afford to live in “crook county!” RE Taxes are a burden to retirees, and so are all the other sales, use, gas, you-name-it taxes. Our daughter and her family left New York last year for Florida, and aren’t looking back! That’s where I think our future lies, seeing as how Illinois is so “ILL” and broke, and yet governor maximus keeps lying to everyong about how the state’s not insolvent! HAH! Anyway, you gotta do what you gotta do. For it looks like Chicago is toast, for all the pols have one thing in common, (save Vallas)…..”stupid is as stupid does!” So quotith Forrest Gump!

  27. Retired in 2018, escaped to Texas in 2019 and haven’t regretted it one bit. You can’t get a good Italian beef sandwich out here but good Texas brisket is an great substitute! Winters here where I’m at (a suburb of Houston) usually last about two weeks, and I’ve already started planting new greenery in my yard. Gonna hit the eighties this week! The public schools where I’m at are actually pretty good, especially when compared to Chicago. Republican Gov. Abbott has recently proposed school vouchers for parents who are dissatisfied with the education their kids are getting and since this is a Republican run state this bill is very likely pass. I shouldn’t publicize this since it might encourage some left leaning Chicago democrats to move over here. We already know the largest influx of legal political refugees are coming from California. There are bumper stickers popping up that righteously state ” ..Don’t California up our Texas”. If you are indecisive about leaving Chicago you should ask yourself : Is it getting better over here? Or is it getting worse? And is this how I want to live? If you answer is no to two of these, it might be time for you to flee. Wherever you end up, I hope you remember the reasons you left and who was responsible for you having to leave. And vote like your life depends on it. Don’t California up our Texas.

  28. You made the correct move.
    I moved in 2013 to San Diego from Joliet for the weather. That part of it paid off.
    But the politics here are abysmal.
    We now live in a relatively safe area in the Eastlake neighborhood of suburban Chula Vista. Our condo complex has a lot of active military. I see them wearing their uniforms. It adds to our sense of security.
    But San Diego itself is a no-go zone after dark.
    Why? There have been numerous shootings in once quiet beach areas such as Pacific Beach and Mission Beach. Our trendy Gaslamp Quarter in downtown is just as bad. It too is a no-go zone after dark.
    When the libs took over, the police were branded the bad guys, the bad guys branded the victims. The rest of us shelter in place when the sun goes down thanks to the Democrats.

  29. Thanks for your story, Steve the Pilot. In many ways, those of us who left Chicago and Illinois share a special sorrow.

    My first childhood home was in Andersonville, and I moved to Lincoln/Belmont area in junior high, when my parents bought their first 2 flat.

    Went to the NW ‘burbs at 18, but always found my way back to visit family and friends.

    Things became progressively, inexorably worse. Finally left IL for safer, freer pastures.

    I miss the Chicago in which I grew up, the city of neighborhoods, the museums, the schools and churches… That was my City. But it is now dead, and I mourn it.

  30. All it took after 46 years in our Oak Park home was a gun pointed at my husband’s chest at 6pm on a beautiful summer evening in July 2021. We too were “forever Chicago”. Planned for a move downtown. Do we miss what was? Heartbroken. Concerts, theater, lakefront picnics, sports, beyond fab restaurants, best bread on planet earth, Symphony Hall, Holy Name cathedral, farmers markets, neighborhoods and neighbors- all. The thugs stole our new car, used it in a gang shootout on the west side, left it near Comiskey, beat to hell, traumatized my husband and myself. We loved you, lived you, and spent big dear Chicago. Life is too precious to be spent waiting for next shootout.

  31. Trying to figure out why all of this is happening; why are the politicians doing this? It could be a perfect storm of dorm room going-to-change-the-world fantasies mixed with pay-to-play corruption and nouveau riche guilt.

  32. The majority of people commenting here have moved to Florida, citing less crime, lower taxes and better weather. I bet most would vote for Paul Vallas if they sill lived here. Yet there Vallas was yesterday, castigating the Chicago FOP and the Florida governor with this: “…there is simply no place in Chicago for a right-wing extremist like Ron DeSantis…”

    Huh? A right-wing extremist? Because he backs the rule of law and freedoms guaranteed in the Constitution and opposes teaching toddlers sex education? WTF?

    Don’t get me wrong. Vallas is obviously the BEST candidate in the running, but he too is a “progressive” who apparently will bow to the demands of those deranged people. Therefore, you ex-pats are right when you say Chicago is a lost cause.

    1. I thought the same re DeSantis. Last time I looked this was a free country and people were able to freely cross state lines, but JB has Illinois on a trajectory course for ruin. My husband and I still recall the day we escaped to northern Wisconsin during the lockdowns! These pols feed on their power and control over us, and it is sickening. I just don’t understand how people can’t see it!? Are they blind?

      This state could sure use some of that “DeSantis extremism” here. The fact that Vallas had to make those comments is sad. He may have been surprised to see that more folks really want more of that common sense here. I wish Vallas had taken a stand for free speech. It brought my opinion of him down a few pegs. So sad to see our city and state being dragged into this progressive hell hole even further.

  33. I grew up in Oak Park but saw the Chicago Way in my family. My father was a partner in the 3-person BEACON PHOTOGRAPH company and the one who had the greatest responsibility. He was the sole commercial photographer, working for large companies such as Wrigley, Illinois Tool Works, etc. He traveled throughout the Chicago area daily to the sites so was in and out of parking garages. They moved the office whenever the rent increased in a building. His last location was on Clinton in the 70s. He needed access to parking to transport the heavy equipment used in that era. He was refused a single parking spot in the nearest Chicago owned garage because he wasn’t anybody in their eyes. Later, I spent some time working in county and state government. I witnessed incompetence in extremely well-paid positions because of family connections. One in particular had anger issues in addition to being ignorant. I have never been a Daley family fan though I recognize they loved the city. They allowed corruption.

  34. Left Illinois 2 years ago after being born in Chicago and living in and around Chicago for 59 years. Chicagofest, Disco Demolition, Sox and Cubs World Series, running/biking along the lake.

    You nailed it Steve on what the best years were. We and our kids were there at that time.

    Once they came of age, they got out. Quick.

    We finally left and live near them…. My son comes over for coffee most mornings.

    Don’t look back. – Mike and Karen in Colorado.

  35. Great story…..unfortunately, your story is spot on. The part about Police Command Officers meeting to tell her how we were going to handle the George Floyd fiasco is true. They brought a retired Officer back with vast and successful experience in handling crowd rioting situations like the Riots ( Oh I’m sorry, peaceful protests), and Lightfoot turned them down. Well, you see what happened. I am born and raised here in Chicago, but it’s time to make a move.

  36. Ridiculous. Generations of politicians have come and gone, some aligned with your ideology, some opposed, no one has ‘died’ as a direct result. This is exactly the inflammatory language that has turned neighbors and family into enemies, and it’s pointless. The protests were a black eye on the city, the moment you break, steal or vandalize you forfeit your POV, regardless of its racial injustice or an insurrection over an election lie. No difference. Crime is a central issue-let’s talk about it. Work/life has fundamentally changed post covid, no one is going back downtown 5 days a week, yet the city was literally designed for that level of occupancy, so what to do? How does the city evolve? You made your decision, god bless. The rest of us are here, waiting for someone to talk directly to issues/challenges versus resigning themselves that ‘everything sucks now and it used to be better..” That isn’t helping. Florida, yes, great weather, beaches are amazing, we love Disney. Governor Ron wants to be Emperor of the United States, thinks that some authoritarian screaming ‘woke’ will get him to the white house-that isn’t going to happen either. I read that Portillo’s opened in Sarasota…

    1. Well, well, well…look who crawled out from under his rock again: Riga tony!
      Tony Cesare, a.k.a. Riga Tony, is an endless troll.
      And he is an identity thief.
      He broke the law when he attempted to steal the identity of the owner of Tony’s Tap in Mineral Point, Wisconsin. They have never heard of of Rigatony or Tony Cesare there. Never.
      He uses a fake name here. Why? He’s an abject coward. Do you see any other fake names here? It’s pure cowardice and a thin attempt to deceive John Kass’ readers.
      He pushes a broom. That’s it.
      Our soon-to-be-released YouTube video will have it all.
      A major potential consequence of identity theft, such as that perpetrated by Tony Cesare a.k.a Rigatony, is that the thief might be able to obtain credit under false pretenses, a federal felony.
      I know of a business in Arizona that was bankrupted by this. That’s Rigatony.
      RigaTony is identity thief, Tony Cesare. Kass calls him the “cockroach in a gas station urinal.” Kass blocked him from his Facebook pages.
      Never reply to him or comment. He will troll you endlessly. He has trolled me.
      Here is the proof of how he attempted to steal the identity of the owner of this place in Wisconsin.
      We called Tony’s Tap in Mineral Point WI. They have never heard of Tony Cesare. NEVER! Here is the proof:


      Or this:

      Stay tuned for our complete expose on Tony Cesare, or Riga Tony, or whoever this identity thief is.
      It’ll be on YouTube soon:
      ‘Riga Tony – Recipe of a Failed Life.’ We have his lies going back ten years.

  37. What a great, but sad story of a once great city. The saddest thing is the ones who can’t afford to escape are the ones hurt the most. Praying voters wake up in the mayoral election. IL can’t survive if Chicago dies and the city is on it’s last breath.

  38. Longtime Chicago resident.
    Left in 1990 for Dubuque Iowa.
    Went to med school in Chicago.
    Trained at the Cook county hospital.
    Great grandfather was the head of the fire department in 1870s.
    Grandpa was a Chicago detective.
    Multiple uncles involved with both electrical union and steamfitters.
    County sheriffs and state police in my family.
    Grew up in Morgan Park loved the neighborhood.
    Raised by great parents with plenty of aunts and uncles and cousins in the vicinity.
    Sadly, families like ours don’t exist like they used to. The nuclear family seems to be something lost in this new culture. Almost an anachronism.
    Not sure if it’ll ever return to Chicago culture.
    Hey John, you may want to ditch the Orvis brand,you’re in Wisconsin.
    Try LaCrosse or St. Croix brand😁
    Less expensive and very functional.

  39. Thank you for your insights. I left Detroit at age 18 in 1982. My city, once the Jewel of the industrial age in the 40s and 50s, had suffered 30 years of rampant corruption on every level of leadership. I knew my future was limited there and I got out. I never went back except several times a year to see my mother and sister. Those that stayed continued to hope. Only after three decades of rock-bottom is Detroit now seeing glimmers of answers to that hope. Chicago is where Detroit was in 1982 when I left.

    Come to Wisconsin. The people are nice, taxes are lower and things seem to still work outside the cities of Milwaukee and Madison. But please please if you come, don’t vote for or put up with the shit that created the uncivilized hole that is Chicago today.

  40. Great article Steve, I can totally relate with the Chicago Way references since my dad had building inspectors visit after voting republican in a primary. It pains me to see Chicago and it’s citizens suffering due to poorly managed government and the greed that comes with it. Good Luck in the sunshine state and Go Lane!

  41. Mr John Kass – Sir, I think that you are falling in to a bit of a rut only presenting personal stories of older/old Chicagoans who have …

    Given up on Chicago the city

    Those who have thrown up their hands, thrown in the towel, moved to Indiana (you) far suburbs or Florida. These are understandable things to do, but it doesn’t exactly inspire confidence, hope for those of us who haven’t give up and run away.

    Yes, our city has lots of terrible problems, car jackings, murder and mayhem, organized mass looting, a BLM, Woke Soros (don’t mention Soros or you WILL BE FIRED) funded DA bad sh** Crazy Kim Foxx. But, it’s not like our city hasn’t had problems in the past Fort Dearborn Massacre, 1871 Great Fire, The Depression, 1967-68 SDS, Wheather Underground and Black A American riots that destroyed the West Side of Chicago which has never recovered.

    How about the late 1980s, early 1990s Crack Cocaine plagues – I was in New York City during this time. Remember when Time Magazine did a cover story ~ 1991 “Are US Cities Dead?” We have corrupt and incompetent, racist hateful BLM pols now like Lightfoot, but back then our Nation’s Capital had an illiterate Black A American crack cocaine addict Marion Barry as mayor, Detroit was ruled by Coleman Young, LA had the Rodney King mass riots, pogroms against Korean Merchants and Orthodox Js in Crown Heights Broooklyn, the rise of race hustler Rev (Al Sharpton). Ok so it’s not like most of my life (born 1961) has been the safe, wholesome 1950s life of President Eisenhower, Leave it to Beaver, Father knows best and Cowboy movies and TV shows where the good guys always win.

    How about featuring, interviewing some younger folks still in Chicago or just outside of the City who haven’t given up?

    All you do is push gloom and doom like the Dwarf “Glum” from the cartoon show who says “We’ll never make it, We’re doomed”.


    Left behind in Chicago but not giving up

    1. Rare instance were Mr Klein and I agree, but here it is. Crime wasn’t a hot button issue here until it moved to downtown post covid. Regarding the lock downs, allowing gambling always confused me but ‘pot’ (its cannabis now) or alcohol were in and out purchases, whereas church is crowds and close proximity. Everyone praises Governor DeSantis for his reaction to covid, but he is blessed with a state of perpetually warm weather and clear skies, try that in Michigan. The riots were a black eye, but as you point we’ve been there before. Watching shows like “The Bear” makes me feel hope for our city, but there is never any hope here, just grievance and grumbling retirees. How about a new perspective? Or perhaps a solution??

  42. Thanks Steve for creating a collective way for us to grieve for our city with each other. I agree with everything you said,and every detailed perspective. We moved to North Carolina this past summer, 7 months now. I want to share some things I miss and will forever miss about Chicago at it’s core. Backstory- born Keeler and Bureau (before it was Old Irving), and took the Montrose bus from age 6 (alone) to 17 to school for private Lutheran education. My game was to memorize every street west, then backwards east. 4 th gen myself. Grandpa owned apartments by St Luke’s hospital on Ashland, a fun day was changing banisters and getting the quarters out of the laundry room.
    Parents retired and moved to a condo at Montrose and Marine Dr til they died. Dad’s joke was next move was Montrose and “in” the lake. He loved Chicago. I’m glad he died right before the pandemic. The erosion of the fabric of the city would have been devastating to him.
    So memories:
    World series of rock at Wrigley field, pink Floyd floating pigs..
    where at a concert your only worry was a sunburn or losing a friend in the bathroom, taking the L, or finding your car. No one got shot. Marshall Field’s windows as a child and drunk Santa’s on Michigan Ave as an adult. Starting a sentence with prepositional phrases mid sentence and yet everyone understood you. My husband always wants me to say the entire sentence and start at the beginning. Why,you all know what I mean. Playing at parks until sundown, because nothing nefarious started until the kids were in and after dinner…it was the gentleman s agreement to keep neighborhoods safe. You all know what I mean. Last December was my last trip downtown at Christmas. As I sat at the bus stop on State street waiting for the bus, I focused on everything around me to absorb it with all my might. The vision of the decorations,the colliding sounds of the bell ringer, traffic, commotion. I knew it was my last time. The faint smell of the fumes radiating up thru the sidewalk vents. Everything familiar. Everything lost. For those of you still there, please vote. Please think. It’s Rome and it’s eroding away in our lifetime.

  43. Spectacular column. Chicago has become a real life “Lion King “ egotistical starring Lori Lightfoot as Scar in an unholy alliance with the hyenas. Jus as the kingdom was ruined, so to the city.

  44. Lightfoot just has to lose – I don’t know if she will, but she is not qualified to run a major city. Unfortunately- there is only one person who has a shot at saving the city and it’s Vallas. The people of Chicago have one chance left to try to get out of this situation- 4 years of another incompetent will be a disaster.

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