Chicago Contrarian, The Podcast
Oct 17, 2026 · 1 hr 8 min · 11 segments
After decades of fiscal recklessness, aldermen in the City Council passed an ordinance raising the benchmark to approve borrowing. Will the mayor pass it? Chicago shells out $260M in police…
Jeff FiedlerPanelistFlorian SunkePanelistJim BoscoHost
Amy JacobsonPanelistPaul, tell us about Mayor Brandon Johnson, the Envy Peddler, and what he was proclaiming this week regarding his plans to tax the rich.
Johnson, you know, he's facing a $882 million budget shortfall by his own admission.
Now, let me point out that he says that his 2027 budget will level the playing field, I'm quoting him, will level the playing field that has allowed corporations to make more money than they've ever made in the history of the world.
And so it's like, I didn't realize that Chicago corporations employed slave labor at one time or another.
But anyway, he also continues to forget, of course, this so-called accomplished history teacher.
and that 280,000 Illinois residents fought for the Union, for the right to free the slaves.
And of course, there were 30, I think 35,000 Illinois Union soldiers who died during the Civil War.
So anyway, he seems to kind of ignore that when he's talking about things like
But look, first of all, let's understand that when he talks about taxing the rich, Nothing he has done has been to tax the rich or to make the revenue generating policies in the city more progressive.
To a certain extent, he is betraying his old progressive constituents because what he's talking about doing in this budget, he has no authority to impose an income tax, certainly not a graduated income tax.
Well, what he's talking about and what he characterizes as taxing these greedy, large corporations, taxing big techs, taxing the ultra-rich, what he's really talking about is imposing what are essentially even higher service taxes on on the use of technology, because he talked about doubling down on his cloud tax, which is already officially the highest tax on computer services in the entire nation, and doubling down on some of his other taxes.
They're passed on to anyone who uses a computer or is accessing the streaming services, is in need of computer services, is in need of technology support.
So whether it's subscriptions, cloud services, or software subscriptions, This is where the tax is falling.
And of course, those taxes bear no relationship to one's ability to pay or even a corporation or a business's ability to pay.
And again, let me point out that these taxes that the city is already imposing are the highest taxes in the entire nation.
Paul, tell us about Mayor Brandon Johnson, the Envy Peddler, and what he was proclaiming this week regarding his plans to tax the rich.
Johnson, you know, he's facing a $882 million budget shortfall by his own admission.
Now, let me point out that he says that his 2027 budget will level the playing field, I'm quoting him, will level the playing field that has allowed corporations to make more money than they've ever made in the history of the world.
And so it's like, I didn't realize that Chicago corporations employed slave labor at one time or another.
But anyway, he also continues to forget, of course, this so-called accomplished history teacher.
and that 280,000 Illinois residents fought for the Union, for the right to free the slaves.
And of course, there were 30, I think 35,000 Illinois Union soldiers who died during the Civil War.
So anyway, he seems to kind of ignore that when he's talking about things like
But look, first of all, let's understand that when he talks about taxing the rich, Nothing he has done has been to tax the rich or to make the revenue generating policies in the city more progressive.
To a certain extent, he is betraying his old progressive constituents because what he's talking about doing in this budget, he has no authority to impose an income tax, certainly not a graduated income tax.
Well, what he's talking about and what he characterizes as taxing these greedy, large corporations, taxing big techs, taxing the ultra-rich, what he's really talking about is imposing what are essentially even higher service taxes on on the use of technology, because he talked about doubling down on his cloud tax, which is already officially the highest tax on computer services in the entire nation, and doubling down on some of his other taxes.
They're passed on to anyone who uses a computer or is accessing the streaming services, is in need of computer services, is in need of technology support.
So whether it's subscriptions, cloud services, or software subscriptions, This is where the tax is falling.
And of course, those taxes bear no relationship to one's ability to pay or even a corporation or a business's ability to pay.
And again, let me point out that these taxes that the city is already imposing are the highest taxes in the entire nation.
The rest of this transcript — segmented and speaker-labeled, so you land on the exact moment something was said
Search every transcript — by keyword, by phrase, or by meaning, across every show Radar indexes
Trends — what is surging across podcasts, measured against its own baseline
Alerts — when a name you follow appears in a newly indexed episode
No account is needed to search Radar.