Leaving Illinois: Another Wealthy Chicago Entrepreneur Votes With His Feet

By Ted Dabrowski of Wirepoints

Illinois keeps losing people it can ill afford to lose.

I recently checked in on a prospective donor who I met in Chicago three years ago. I didn’t know him at all back then, but it was easy to get a sense he cared deeply about Illinois. His passion for fixing Chicago’s problems was obvious from the moment I met him.

He was everything Chicago should want from someone in the business community. An engaged and highly successful investor, tech entrepreneur and C-suite executive. Politically active yet still willing to get his hands dirty on real policy issues. Not scared to take on politicians. Paid lots in taxes, too.

To my disappointment, he told us he’d fled Illinois. He was one of the 114,000 Illinois lost in population this year. Here was his email response to a Wirepoints end-of-year request for financial support:

“Good to hear from you and glad all is going well.

I have bailed on Illinois. I’m now a resident of a great state out West. God knows I tried to be a loyal Illinoisan! They say that in the marketplace people vote with their pocketbooks. In Illinois, people are voting with their feet.”

In our line of work, we hear daily from Illinoisans who recently left the state for greener pastures. Illinois is the nation’s second-biggest net loser of tax filers so that’s not a surprise. Most who’ve left are happy to have shed the high property taxes, worsening crime rate and overall disrespect for residents that’s embedded in everyday Illinois corruption.

But I didn’t expect this guy to leave. He’s a player that donates to both sides of the political aisle. He’s advised lawmakers on how to bring down debts, he’s fought against tax hikes and he’s helped raise funds for political campaigns. I figured he was loving mixing it up with Lori Lightfoot like he did in the past with previous city officials. 

That’s why I called him directly to dig deeper: 

“I love Chicago and I left very reluctantly. I have been intimately involved with trying to resurrect the state, the county and Chicago, but they are all on a path to destruction. Only the open coffers of the federal government is helping them in the short term. And that’s got them spending money on programs that they have no ability to pay for on an ongoing basis.

Illinois is, in blunt terms, no longer going down the sewer. It’s already there. What did they call it in Roman times? Cloaca Maxima. It’s there. When you look at the state’s finances, it’s impossible for Illinois to resurrect itself. It’s just not gonna happen.”

This Chicagoan was one of about 3,000 wealthy taxpayers that Illinois loses, on net, each year. (In 2019, Illinois lost to other states 6,400 tax filers with incomes greater than $200K, while just 3,000 such filers moved into Illinois.)

And when they leave, those people take their families, their incomes, their wealth and their entrepreneurship with them.

Sadly, it’s the same story for every income group in Illinois (see Appendix). This state is being hollowed out.

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This same time last year I told The Illinois Channel’s Terry Martin that the state’s leaders had no plan to fix the state in 2021. That hasn’t changed in 2022.

They have no plan to reverse the destructive surge in crime. Nothing is being done about the state’s broken finances except the recent begging for more federal handouts. There hasn’t been a peep about cutting property taxes ever since Gov. Pritzker’s failed commission did nothing. And the education system is getting worse by the day. 

Illinoisans can increasingly smell those failures. Cloaca Maxima, indeed.

P.S. That’s not to say there’s no plan. Wirepoints has developed a baseline solution to Illinois’ biggest problem: the pension crisis. Our new Pension Solutions page breaks down the crisis, why it happened and what we can do about it. We also have a whole host of other reforms Illinois should pursue to turn this state around.