Rebuilding Chicago: An Exit Analysis Provides Clues to Fixing Things

February 27, 2023

A business guy does “win/loss” analysis for why he left Chicago starting with a decline of the lakefront

In my career, this author always found “win/loss” analysis in business invaluable. Learning specifically why someone bought your product or service (or, more importantly, why they didn’t) over others is invaluable to know, especially the qualitative reasons they decided to move in one direction or another.

This is my own “win/loss” – specific “loss” – analysis for Chicago. I’m one of “those people” who left the city (for a neighboring state and Florida) permanently last year. Yet that was never our original plan. My wife and I had intended to raise all of our kids in the city and continue to build businesses -- and invest in others --in our backyard.

Understanding why we left might hold the keys to getting families like us back.

I’m deadly serious here. Because believe me, I would love nothing more than to return to Chicago at some point, at least on a part-time basis each year. But I don’t see it happening in my lifetime without radical change that addresses the three reasons we left, linked by a commonality of city, county and state government waste, malfeasance and apathy.

The first reason we left the city may surprise some: Chicago is no longer a place to appreciate the natural surroundings and environment, something which originally attracted so many people here, including us.

Decline of the lakefront

The first thing we noticed when we left Chicago was how much more free we felt outside of the city, in nature, and how Chicago’s natural spaces had become dirty and unsafe. And besides, from a dwelling perspective, after spending just about our entire lives looking at alleys and other buildings in New York, Chicago, and other cities, getting out in nature all the time simply made us happy, much as walking around the bird sanctuary at Montrose did in Chicago back when it was safe to walk along the lakefront at dusk and dawn.

Leaving Chicago during the COVID-19 pandemic for a much less affluent community with spectacular nature – even if it lacked in other things such as good, casual restaurants – that was only a reasonable train or car ride away from downtown was a trade off that we realized was a no brainer in the end. Of course it also helped that our property taxes were one-eighth of that in Chicago.

Being in nature outside the city reminded us one reason we loved Chicago so much, back in the day, was the glorious lakefront which we used from the South Side all the way up to Bryn Mawr on a weekly basis (even in winter). I probably have logged 7,500 miles of running on the Chicago lakefront over the years.

I loved the lakefront. And lived on it, back when it was gorgeous and safe as opposed to a progressive equity experiment gone horribly wrong.

But today, the lakefront is not only looking shabby compared to the past (think flowers on Lake Shore Drive – the reverse of broken windows policy under Daly and Emmanuel), it simply is not safe anymore, as recent major crime data suggests. The growing homeless cities – they are now beyond “encampments” as many have dozens of tents with communal cooking and toilet facilities – under and around the viaducts and under passes on Lake Shore don’t help the problem and make getting back to your home after a run or walk an unpleasant and risky experience, especially if you identify as a birthing or egg producing person.

The Chicago lakefront was the city’s treasure – something that attracted thousands to the city before it went downhill, including me. Ken Griffin realized this when he donated tens of millions of dollars to expand the lakeshore bike path. As did Rahm, when I saw him dozens of times jogging with his detail on the old single path before Griffin’s generosity to expand it (before he left for Florida, where I write this essay not too far away).

The lakeshore is so important to a turnaround of Chicago that I believe we must separate it out from the broader crime issue plaguing the larger city. After all, without a magnet to attract people, everything else will simply repulse those who would even consider a move to (or back) to Chicago.

Exit analysis lesson #1: For Chicago to get its mojo back for families (many of whom value the outdoors), a safe, clean and natural lakefront is absolutely critical. Chicago should over-invest in everything along the lake – landscaping, flowers, safety, etc.

Crime and punishment

I will sound like a broken record by pointing out Chicago’s crime issues. But when COVID hit and then our neighborhood, and those around it, were ransacked by BLM riots as the city turned a blind eye – and as our kids’ schools encouraged it from the classroom – we knew that we had to leave the city permanently.

Beyond the riots, in our old neighborhood, we observed (without even consulting CWB to hear about rapes, murders and homicides in Lakeview):

  • An attempted break-in (for the first time in 40 years) in our “fortress” apartment building with 24-hour security 
  • A dramatic increase in violent assaults and muggings within a two block radius of our home including multiple victims we knew well 
  • Someone getting shot walking his dog in the park in front of our building (as part of a robbery attempt)
  • Drive-by shootings on Lake Shore Drive which we could hear at night
  • Dozens of car jackings within 500 meters of our apartment (in a matter of weeks) 
  • A dramatic increase in violent crime at our L stop (which suggested you would have to be an absolutely idiot to take the purple, brown or red lines if you could avoid them, even at rush hour) 
  • Increased hit and runs in our neighborhood (with no police presence to enforce traffic laws) including fatalities 

Exit analysis lesson #2: Chicago, of course, has done nothing to fix the crime issues on the Northside. Yes, it’s a complex, potentially intractable issue given that police have no incentive to do their job, and Kim Foxx is a public defender rather than a prosecutor. But the city must do something dramatic here. And soon. Or crime alone will create a death spiral of wealthy families leaving (yes, those “oppressors” who create jobs) as more become victims themselves.

Educational standards and excellence

Everything you hear about “critical race theory” and “gender ideology” on the news in Chicago schools is true. I saw it first hand during distance learning in public and private schools with my kids.

On the high school level, it’s happening in select enrollment schools. And it’s happening in private schools as the “butt plug dean” at Francis Parker – who kept his job mind you even after parental outcry which is the real shocker – taught us as well, anal lube, fisting instructions and all.

I won’t focus on how these educational philosophies deny the rights of students, teachers and parents to disagree with them, since you’re only a gender ally or anti-racist when you admit that white supremacy and cis heteronormalcy is the issue.

No, the fundamental issue is cratering academic standards, across the state in fact. Test scores and proficiency in math and reading are dropping even as educators and schools negotiate for more authority over our children’s lives. We saw this as our youngest child was behind grade level in Chicago in reading (which we only learned moving out of the state), but was caught up after a year of 2-hours of homework a night for his new school.

Even at top Chicago private schools (our child above who was behind grade level attended one of them), intersectionality, equity and gender ideology is replacing excellence as the focus. But not that this matters anymore for oppressors (e.g., Asian, Jewish and white kids who attend these schools). Those without the right intersectional victim street cred are simply not getting into good colleges as a general rule, even when they come from the so-called best Chicago high schools with top grades and perfect test scores.

Compare the college matriculation list 10 years ago at Whitney, Lane, Northside, Payton, Parker, Latin, Lab, Ignatius, etc., with today (the actual number of students attending a school each year – not the admitted list since that could be a single student getting into multiple schools).

In short: unless you check the box as black, Hispanic or LGBTQ (hmmm, maybe your child should, since gender and sexual identity are fluid and can change :-), you’re simply not getting into an Ivy or equivalent school unless you’re a legacy (who applies early) or an athlete. Yet if you’re on the “victim matrix,” you don’t even have to submit your test scores anymore and, voila, you’re in.

Of course Chicago can’t fix the issue of the complete elimination of merit and hard work as the primary criteria for college admissions (even if the Supreme Court is about to) nor its overt racism to whites and Asians in education, politics and the media (thank you Lori Lightfoot and Toni Preckwinkle). Not to mention the omnipresent woke anti-Semitism from the same politicians starting with the refusal to condemn the BLM and pro-Palestinian riots and social media air cover.

But Chicago can and should blow-up CPS and the CTU and figure out how with its gigantic budget ($29K per student). Note: this cost per student is generally two or even three times that of private, public, charter and parochial schools with far superior outcomes in neighboring states. Only by providing alternatives to the selfish iron fist of the CPS and the CTU, and giving that money to families in the form of vouchers and school choice, can Chicago’s educational system come back from the grave it currently lives in.

Exit analysis lesson #3: There is no “my truth” in math and reading proficiency. Chicago schools can only hide beyond the facade of gender ideology, equity and anti-racism programs for so long. The real threat is the systematic elimination of academic standards despite a ginormous budget per student which clearly is not having any impact on student proficiency. “DEI,” “equity” and “privilege” rhetoric is simply air cover for a failed educational system in Chicago. This includes private schools as well whose recent college matriculations lists and early acceptances for the 2023-2024 year suggest an absolutely abysmal ROI for most parents – one that’s only getting worse.

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