May 20

May 20 Tax the Rich

Chicago, CTA, Demonstrations, Donald J. Trump, Parades, Performance, Protest, Public Declarations

At 4:00 PM today, 75 demonstrators gathered on the corner of Belmont and North Wilton Avenue, across from Reckless Records. This would be a refreshing demonstration whatever transpired because it was being held at a relatively obscure Lakeview location. The people who live and shop in this neighborhood typically must head to the Loop to take part in rallies and marches.

Undoubtedly, I had seen many of these demonstrators at other rallies and marches, including the “No Kings” rallies. Nevertheless, nobody, including the organizers and speakers, looked familiar.

After one speech on the street corner, the group marched from Wilton Avenue to Sheffield, where they headed west for less than a block until they arrived at Illinois State Representative Margaret Croke’s office. Five or six people delivered speeches calling for an increase in state and local taxes. The demonstrators were calling for a $4 billion increase, which would be used to provide childcare, healthcare and housing for everyone. Additionally, they demanded that more schools be built and that programs be established to support crime victims.

As I have noted before, the demonstrators at “Tax the Rich” demonstrations hold totally unrealistic expectations. Both the State of Illinois and the City of Chicago are already functionally bankrupt. In the city’s case, it has $41.1 billion in outstanding municipal debt, including roughly $4.5 billion in unfunded pension liabilities. Put in more personal terms, to repay the debt in total, every Chicagoan (including the children) would have to contribute $42,600 in additional taxes.

The State of Illinois also finds itself in dire financial circumstances. According to Americans for Prosperity (“AFP”), Illinois has “the highest combined state and local tax burden in the nation at 16.48% of median household income.” Not surprisingly, Illinois has had the lowest bond rating for the last 13 years, which means higher finance costs for the state. Of all 50 states, Illinois is the only one with over $100 billion in unfunded state pension liabilities, coming in at $145.5 billion.

The demonstrators fail to recognize that Illinois is not the Federal government. When taxes head upward, wealthy Illinois residents can leave the state, as billionaire hedge fund CEO Kenneth Griffin did in 2022, when he relocated his business and family to Miami, Florida. In addition to losing Griffin as a taxpayer, the State of Illinois and the City of Chicago lost a philanthropist. Griffin made significant enough contributions to the Art Institute and the Museum of Science Industry so as to warrant naming rights. He is not the only one who has left the state, as the record level of vacant office space in the Loop aptly demonstrates. Or as a law partner of mine said over three decades ago, “With the Internet and cheap telecommunication services, you can run your business from anywhere.”

The problem with the “Tax the Rich” crowd is that they have no idea what things cost and just how much a billion dollars represents. It is seriously open to question whether those in the top quintile or the top one-percent fail to pay their fair share. According to an article published by the Peter G. Peterson Foundation, in 2022 the top one-percent paid 31% of all Federal taxes—individual income, payroll, corporate income, estate, and excise taxes. Those in the top quintile paid 25% of all taxes.

The Tax Foundation shared similar findings. In 2022, the top one-percent paid 40.4% of total Federal income taxes, while the top 25% paid 87.2%. On the other end of the spectrum, the bottom 50% paid 3.0% of total Federal income taxes.

As for progressivity, the bottom 50% of taxpayers paid an average income tax rate of 3.7%, while the top one-percent paid an average income tax rate of 26.1%. These numbers undermine the argument that the rich are not paying their “fair share,” or significantly more than the those with lower incomes. “Fairness” is in the eye of the beholder.

According to those rallying outside of Representative Croke’s office, a wealth tax is one solution As a general proposition, people are very bad at assessing large numbers, as was once again evident today. According to a September 2, 2025 article in the Wall Street Journal, there were 1,135 billionaires in the U.S. in 2024, with a collective net worth of $5.7 trillion, which is a lot of money, but relatively speaking, how much money?

To put the $5.7 trillion number in perspective, according to the Congressional Budget Office, the federal government will have a $1.9 trillion budget deficit in 2026, which will grow to $3.1 trillion by 2036. In other words, if the federal government confiscated all the assets held by billionaires, the government would have enough money to eliminate the federal budget deficit for just three years. Then who is going to cover the federal budget deficit?

As is true in the case of drastically increased Social Security and Medicare benefits, the only way to fund social services on the scale that the demonstrators were demanding today is to increase taxes on the middle class because there simply are enough “rich” people. Those making demands today would be shocked to learn that only they can help fund the social services they are calling for with higher taxes on themselves.

Having demonstrated the fallacy that the billionaire class are the only ones who should and can fund social services on a much larger scale, I should note that the billionaires deserve blame for the public misconceptions about the extent of billionaire wealth. Jeff Bezos, Elon Musk, Mark Zuckerberg, and the other tech Bros have turned right, being seen often in the company of Donald J. Trump and up on Capitol Hill. It is not unusual to see these folks walking the red carpets at galas and balls, where tables can cost well over $100,000.

The tech Bros have a huge image problem, which is fueling the calls for soaking them with confiscatory taxes. While the tech Bros might not be able to totally eliminate their abysmal image in the eyes of the public, the Bros At 4:00 PM today, 75 demonstrators gathered on the corner of Belmont and North Wilton Avenue, across from Reckless Records. This would be a refreshing demonstration whatever transpired because it was being held at a relatively obscure Lakeview location. The people who live and shop in this neighborhood typically must head to the Loop to take part in rallies and marches.

Undoubtedly, I had seen many of these demonstrators at other rallies and marches, including the “No Kings” rallies. Nevertheless, nobody, including the organizers and speakers, looked familiar. '

After one speech on the street corner, the group marched from Wilton Avenue to Sheffield, where they headed west for less than a block until they arrived at Illinois State Representative Margaret Croke’s office. Five or six people delivered speeches calling for an increase in state and local taxes. The demonstrators were calling for a $4 billion increase, which would be used to provide child care, healthcare and housing for everyone. Additionally, they demanded that more schools be built and that programs be established to support crime victims.

As I have noted before, the demonstrators at “Tax the Rich” demonstrations have totally unrealistic expectations. Both the State of Illinois and the City of Chicago are already functionally bankrupt. In the city’s case, it has $41.1 billion in outstanding municipal debt, including roughly $4.5 billion in unfunded pension liabilities. Put in more personal terms, to repay the debt in total, every Chicagoan would have to contribute $42,600.

The demonstrators fail to recognize that Illinois is not the Federal government. When taxes go up, wealthy Illinois residents can leave the state, as billionaire hedge fund CEO Kenneth Griffin did in 2022, when he relocated his business and family to Miami, Florida. In addition to losing Griffin as a taxpayer, the State of Illinois and the City of Chicago lost a philanthropist. Griffin made significant enough contributions to the Art Institute and the Museum of Science Industry so as to warrant naming rights.

The problem with the “Tax the Rich” crowd is that they have no idea what things cost and just how much a billion is. It is seriously open to question whether those in the top quintile or the top one-percent fail to pay their fair share. According to an article published by the Peter G. Peterson Foundation, in 2022 the top one-percent paid 31% of all Federal taxes—individual income, payroll, corporate income, estate, and excise taxes. Those in the top quintile paid 25% of all taxes.

The Tax Foundation reports similar findings. In 2022, the top one-percent paid 40.4% of total Federal income taxes, while the top 25% paid 87.2%. On the other end of the spectrum, the bottom 50% paid 3.0% of total Federal income taxes.

As for progressivity, the bottom 50% of taxpayers paid an average income tax rate of 3.7%, while the top one-percent paid an average income tax rate of 26.1%

These numbers undermine the argument that the rich are not paying their “fair share,” or significantly more than the those with lower incomes. “Fairness” is in the eye of the beholder.

As is true in the case of drastically increased Social Security and Medicare benefits, the only way to fund social services on the scale that the demonstrators were demanding today is to increase taxes on the middle class because there simply are enough “rich” people. Those making demands today would be shocked to learn that they only they can help fund the social services they are calling for with higher taxes on themselves.

Having demonstrated the fallacy that the billionaire class are the only ones who can fund social services on a much larger scale, I should note that the billionaires deserve blame for the public misconceptions about the extent of billionaire wealth. Jeff Bezos, Elon Musk, Mark Zuckerberg, and other tech Bros have turned right, being seen often in the company of Donald J. Trump and up on Capitol Hill. It is not unusual to see these folks walking the red carpets at galas and balls, where tables can cost well over $100,000.

The tech Bros have a huge image problem, which is fueling the calls for soaking them with increased taxes. While the Bros might not be able to totally change public perceptions, the Bros could improve public perceptions by making significant contributions to charity now rather than promising to make contributions upon their deaths. They could also burnish their images by stepping out of the limelight and out of politics. In other words, by shutting up.

Representative Croke has her own public relations problems. If she was in her office, why didn’t she step outside to address her constituents?

[Click on an Image to Enlarge It. The Images Are Not Necessarily in Exact Chronological Order]