Friday, February 27, 2026

The Race To Bankruptcy Court: The Bears Likely Fleeing Chicago, Chicago Goes Bankrupt In About Decade, and Palantir Flees To Florida

 It seems we are in a little bit of a rut in that we seem to be getting overwhelmed with news about our choice for states and major cities that are likely to go bankrupt relatively soon. As always, our top state governments that we think are nearing bankruptcy include New York, New Jersey, Illinois, and California. Our top major cities we think are rapidly approaching bankruptcy include New York City, Chicago, Los Angeles, and San Francisco.

Before reviewing the latest news and seeing which state or city is  making the best progress towards government bankruptcy, let’s review how these cities and states got themselves into this financial death spiral  position to  begin with:

  • A government entity keeps expanding its budget, eventually putting pressure on the tax revenue stream it receives.

  • At some  point, rather than cut government spending or make its programs more efficient financially, the politicians in charge raise taxes  to meet the ever growing government expenditures.

  • The raising of taxes causes some residents and businesses to leave the city or state for less tax burdensome areas, reducing the tax base and  reducing  the revenue stream.

  • Rather than cut expenses and become more efficient to match the reduced tax revenue stream, politicians in the above cities or states raise the tax burden even  more.

  • This causes more residents and businesses to flee the city or state, further reducing the tax base and tax revenue stream.

  • At some point politicians panic and raise taxes more and start cutting vital government services (e.g. police, fire, education) in order to try and balance government spending against the shrinking tax base and  revenue stream.

  • The reduction in quality of government services in particular and quality of life in general  drives more residents and businesses out of the area.

  • Eventually, the expenses, costs and financial liabilities outstrip the reduced tax stream and bankruptcy occurs.

Okay that’s the process, now lets check the progress some of  the above listed government  entities are making to  achieve this bankruptcy goal:

1)Business and residents have been fleeing Chicago for a while now due to high taxes, high crime rates, faulty management skills of the politicians running the city government, etc. Major companies that have made major moves out of Chicago  include Boeing, Citadel Financial, Tyson Foods,  Caterpillar, and others. The CEO of Citadel, Ken Griffin, told the Wall Street Journal that his co-workers feared getting mugged and attacked on the streets of Chicago which was a driving force for the relocation to Florida.

Consider the following numbers:

  • According to the Illinois Policy Institute, during the tenure of the current state governor, J.B. Pritzker, there have been 49 state tax hikes since 2019. 

  • These tax hikes have  raised the average resident tax burden by 44%.

  • The state has  lost at least ten major corporate headquarters in the past six years.

  • Since 2019, the state GDP has  grown at only about one third the rate of  the national  GDP growth.

But it is not just residents and businesses leaving the city:

  • The Chicago Bears have called Chicago their home for over 100 years, beginning back in 1920.

  • An  original NFL franchise, the words “Bears” and "Chicago" have  been inseparable for so  long.

  • But now there  is a good chance that even the town’s  historic NFL franchise has  had  enough of the city and are  seriously considering leaving the city, and the state, and heading to a new home in  northern Indiana.

  • Despite negotiations directly with the state’s governor, J.B. Pritzker, it looks like the Bears are leaving.

  • Indiana politicians are moving quickly to put a package together that will steal the Bears away while Illinois and Chicago politicians have dithered for years without coming up with a good plan to keep the Bears in the city.

When you lose a 100 year institution like the Bears leaving the city and state, when residents and businesses cannot wait to leave the city of Chicago and the state of Illinois, you have a strong case for either Chicago or Illinois governments entering bankruptcy pretty soon.

2)The Chicago Contrarian website recently published an in-depth article and  analysis on the financial disaster that is the Chicago city government. But the big news is that they not only outlined the dire financial situation of the city but also forecasted when the city would actually go bankrupt:


  • The opening paragraph of the  article summed up the situation quite nicely by claiming “It’s only a matter  of time” before the city’s revenues cannot pay off the city’s expenses and financial obligations.

  • The article maintains that the previous mayor’s  administration of Lori Lightfoot heavily contributed to the  financial mess but that local politicians set Chicago off on a financial death spiral long before she came along.

  • The theory is that local politicians sold off the financial future of Chicago by lavishing lucrative salary, pension, and benefit programs on city union workers in exchange for their votes.

  • In order to  finance the city’s massive pension fund liabilities for retired and future retired city employees as well as operate the city on a day to  day basis,, the city has to fund those pension obligations and current expenses off of a shrinking tax base.

  • Unfortunately, over time the city’s politicians have underfunded those future pension liabilities with the police, fire, and  municipal workers pension funds currently funded at less than 30% of what they will need to pay out over time.

  • These low funding levels to cover future pension  liabilities are at about the same  level Detroit had before it  went bankrupt.

  • In the Contrarian  article, the point is  made that the city is not allowed to cut benefit levels because that is prohibited by the Illinois Constitution.

  • In fact, things are already so  bad that the city is actually borrowing money to pay for current financial obligations while at the same time increasing those future costs of servicing the money it  is  borrowing today.

  • So  a shrinking tax base  which  leads to  shrinking tax revenue streams with growing pension and other employee obligations that cannot be  legally reduced and you have a vicious financial death spiral.

  • In fact, the article, using the city’s own actuarial analyses, predicts that the city will  go bankrupt in 7 to 12 years

  • But the state politicians in Illinois have passed legislation that does not allow Chicago or any other state city to declare bankruptcy.

  • Thus, it is unknown  territory of what happens when Chicago can no longer  fund its current  operating city expenses and its pension and other union benefits which makes it bankrupt but cannot legally be bankrupt, quite the conundrum.


Thus, what happens when the city is out of money and cannot legally go bankrupt:


  • One option would be to  drastically cut government services (fire, police education, etc.) but that option would drive more residents and businesses out  of the city further reducing an already dwindling tax base.

  • The city could raise property tax rates and other taxes but that would also drive people out of  the city and further reduce the tax revenue stream.

  • The city or a judge could force the  state government to  change the law and allow the city to declare bankruptcy and then go through a judicial process to fix the financial  situation which would obviously involve slashing benefits and salaries of union workers  and city retirees which would have catastrophic political impacts on  the Democrats ruling the state and city.

  • It could hope to  get a bailout from the Federal government which is highly unlikely since those people  living outside of Illinois are not going to allow their tax dollars to go to bail out a failed  political problem in Chicago.


Get the popcorn because it is  going to be a wild ride since in as early as seven years the city will  go bankrupt in reality but not  legally, it will  not have enough  revenue to pay its  expenses and  financial  obligations but will have to anyway, what a mess.


The bigger question  now becomes whether Mamdani in New York City, Karen  Bass in Los Angeles or any number of other cities (Portland and Seattle) can beat that seven year window  to bankruptcy court.


The  entire Contrarian  article can  be  viewed at the following  link:


https://www.chicagocontrarian.com/blog/when-is-chicago-going-bankrupt#:~:text=Bankruptcy%20isn't%20legal%20%E2%80%94%20yet&text=And%20Illinois%2C%20in%20its%20infinite,Assembly%20passes%20legislation%20authorizing%20it.


3)One last example  of what is going on in cities and states across  the country that are facing a financial death spiral:


  • Palantir is a major AI  technology company.

  • It recently announced that it  is moving its corporate base to the state of Florida which is one of the least burdensome tax states and one of the most welcoming states of businesses.

  • The company had escaped from the high tax/high regulation state of California in 2020, taking its high salary and high tax paying employees with them, giving that state another blow of an exiting company.

  • They moved to Denver but have now fled that state for Florida where taxes and business regulation are lower.

  • The company is  valued at $300 billion so this move to Florida is a pretty big deal.


Florida and other states continue to gather up residents and businesses that are leaving the high tax/high business regulation states like our prime candidates to go  bankrupt: New York,  New Jersey, California,  and Illinois.  At some point the financial bastions of these states, e.g. Silicon Valley in California, Wall Street in New York, Chicago Bears in  Chicago, etc., get hollowed out and the functions they once owned get reincarnated in other states.


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If you agree that we need to deseat every member of Congress for their lack of success and accomplishment, then please consider going to the following petition link to help the cause:


https://www.change.org/p/deseat-congress-reset-freedom



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Our book, "Love My Country, Loathe My Government - Fifty First Steps To Restoring Our Freedom And Destroying The American Political Class" is now available at:


Sunday, February 22, 2026

The Race To Bankruptcy Court: An Update On the City and State Government Races

 Over the past few posts we have  made the case that New York City is in  the lead to be the next major U.S. city to go bankrupt. The new mayor, Zohran  Mamdani, is already in budget problems and budget shortfalls, making his campaign promises look moot since he does not have enough money to pay for those promises. In fact, he does not have enough tax revenue to pay for basic city services, being over $5 billion short relative to the next fiscal year budget.


But today let’s see how other prime candidates for government bankruptcy are doing in  their financial death spiral. As you may know, our top state candidates to go bankrupt include New York, New Jersey, Illinois, and California. Our top city government candidates to go bankrupt include New York City, Chicago, Los Amglees, and San Francisco (although a couple of west coast cities are making late moves in this bankruptcy race, Portland and Seattle).


But before reviewing the financial status of the above government entities, let’s review how the financial death spiral and eventual bankruptcy will unfold:


  • A government entity keeps expanding its budget, eventually putting pressure on the tax revenue stream it receives.

  • At some  point, rather than cut government spending or make its programs more efficient financially, the politicians in charge raise taxes  to meet the ever growing government expenditures.

  • The raising of taxes causes some residents and businesses to leave the city or state for less tax burdensome areas, reducing the tax base and  reducing  the revenue stream.

  • Rather than cut expenses and become more efficient to match the reduced tax revenue stream, politicians in the above cities or states raise the tax burden even  more.

  • This causes more residents and businesses to flee the city or state, further reducing the tax base and tax revenue stream.

  • At some point politicians panic and raise taxes more and start cutting vital government services (e.g. police, fire, education) in order to try and balance government spending against the shrinking tax base and  revenue stream.

  • The reduction in quality of government services in particular and quality of life in general  drives more residents and businesses out of the area.

  • Eventually, the expenses, costs and financial liabilities outstrip the reduced tax stream and bankruptcy occurs.


1)Let’s  start this update with the situation out in California:


  • We have already reviewed numerous times how residents and  businesses are fleeing the state due to high tax burdens, high utility costs, high gas costs, high crime rates, high business regulation burdens, etc.

  • Businesses that have moved their operations in total or in part out of California include Tesla, Schwab, Toyota, and other small and large businesses.

  • Residents have  also been fleeing, creating a smaller tax base and  smaller tax revenue  stream for the state government.

  • Rather than reduce taxes and/or make state government operations more efficient  to match the outflow of taxable assets, there is a movement to impose a so-called “wealth tax” on the wealthiest Californians, not an  income tax but a wealth tax on the total  assets of individuals, not their income.

  • Billionaire founders of Google, Facebook, and Paypal have  already moved their operations and lives to Florida to avoid both the current high tax burden of California and obviously not wanting any part of the wealth tax.

  • But it is not just high tech founders moving out of the state with news reports indicating that Hollywood stalwart, Steven Spielberg, has already moved out of California, relocating to Manhattan in NYC.

  • Whether he moved out of California to avoid the wealth tax or it is to stay closer to family,  his explanation for the move, it is another very rich California who will be trying to avoid the wealth tax if it ever becomes a reality.


Whatever the motivation was for Spielberg’s move, in any case California will not be getting his current state tax revenue going forward, never  mind getting his wealth tax bite. Raise taxes enough and those that can most easily afford to move out from under the tax burden will do just that: move elsewhere and take their tax stream with them.


2)One state we have not discussed that is on the path to bankruptcy is the state of Virginia. However, recent actions by the state’s politicians open up the possibility that they will also start down the path to bankruptcy:


  • One of the first things the state politicians did in the state legislature in January was to impose a slew of new taxes on a large variety of products and services.

  • In a stunning  move of hypocrisy, right after politicians imposed a whole host of taxes on every state resident and business, a member of the legislature is proposing that the salary for members of the legislation get tripled.

  • So it appears that the state political class has no problem significantly  increasing the taxation of its residents and businesses while rewarding themselves for no good reason.

  • And as we have  discussed in a recent post, while the states around Virginia have been working at reducing or eliminating their own state income tax programs, giving their residents back some of their earning power, that does not appear to be in the genetic makeup of current Virginian politicians.


And to compound this driving up of the tax burden on state residents, a major company has already announced that it is moving a significant Virginia business presence and tax stream out of state:


  • In a possible leading  indicator of business out migration, Boeing has announced it will move its Defense, Space, and Security headquarters out of its current home in Alexandria, Virginia.

  • It will move this division’s entire operations to St. Louis, Missouri.

  • This will take almost 400 highly paid, and highly taxed, employees out of the state to the benefit of  Missouri.

  • When the transfer to  MIssouri was announced,  Boeing also announced major investments in that area  of their business, a major investment that will not happen inVirginia.


While Virginia is not in imminent danger of going  bankrupt, these latest developments from the state’s political  class are early leading indicators of behavior that drive the out-migration of residents and businesses as the state government increases the tax burden on their tax base.


3)A brief diversion back to New York City’s race to bankruptcy court. The city currently cannot fulfill its current government responsibilities, given it could not remove snow and garbage during a recent snow storm and it could not prevent about 20 individuals from freezing during that storm. Given a $5.4 billion budget deficit for the next fiscal year, Mamadani will have  difficulty implementing all of his free promises he made during the campaign: free buses, free daycare, free college tuition, etc.


And yet he has devoted millions upon millions of dollars towards government equity programs in his budget, programs that will  do absolutely nothing for the  benefit of city residents. And according to Joe Rogan, not only does Mamadani want to waste millions of dollars on  stupid gender, race, and sexual DEI programs,  he  also wants to  spend a whopping $1.2 billion on illegal immigrant care.


Garbage and snow does not get removed. People are freezing on  city streets. The budget will likely require cuts to essential  city services. And he wants to spend over a billion dollars on people that should not even be here in the country in the first place. 


As city residents and businesses see their tax dollars going to waste like this while city services stink, more and more will decide to head  out of the city for more sane, less burdensome taxation areas, making the current $5.4 billion budget deficit look good against future rising deficits.


4)One of our favorite state governments to go bankrupt includes the state of Illinois. The state government has unfunded liabilities extending far into the future at the same time that residents and businesses are fleeing both the state and its largest city, Chicago. 


And as always rather than rein in spending to be in line with the state government’s  shrinking tax base or make  government  operations more  efficient, the latest budget proposal from the state’s governor calls for increased taxes:


  • Illinois Governor J.B. Pritzker’s proposed budget calls for the highest level of state government  spending ever.

  • He needs to  close an expected $2.2 billion budget shortfall and thus, as always, he calls for tax increases of over $700  million.

  • He wants a wacky “social media tax” on large  social media  platforms, an idea that likely cannot even be implemented.

  • His tax increase proposals require increased taxes on both businesses and residents.

  • He wants to keep more state money for the state government and deprive local governments of their typical share of state tax money, an action that will  likely result in local government tax increases to make up for the $60 million shortfall.

More taxes, more taxes, more taxes. Do these people never learn? The state has been bleeding businesses, residents, and tax base for years and they still do not understand: when government  services get worse and  worse, when taxes and business regulations get more and more burdensome, people will  look for opportunities to  move to other places where they have more freedom to keep their hard earned wealth.

That will  do it for today: politicians in these financial death spiral cities and states do not get it: you cannot keep rising taxes on residents and businesses without seeing those same residents  and  businesses eventually getting fed up with the process and taking their tax revenue streams elsewhere. It is basic human  nature.


Coming attraction: while our current position is that New York City will be the next major city to go bankrupt, our next post, based on  some in-depth statistical  and  financial analysis, makes a strong case that Chicago will win that race to bankruptcy court. It is  still our contention  that Illinois will be  the first state government to go bankrupt, holding  off California (just barely),  New York and New Jersey.

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If you agree that we need to deseat every member of Congress for their lack of success and accomplishment, then please consider going to the following petition link to help the cause:


https://www.change.org/p/deseat-congress-reset-freedom



**********************


Our book, "Love My Country, Loathe My Government - Fifty First Steps To Restoring Our Freedom And Destroying The American Political Class" is now available at: