this post was submitted on 06 Sep 2025
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Why Chicago? Not American but curious.
Because it's a big democrat stronghold. And he's racist.
Probably several real reasons... and i think he just throws shit at the wall until he finds something that sticks but this one stuck because among his followers it ticks several boxes...
He already did a dry run in Los Angeles, literally chasing harmless day laborers through Home Depot parking lots. Newsom (Cali Gov) made it more difficult by trolling him on social media. (I realize how insane that sounds but he just has the temperament of a teenage boy). So he is probably thinking of something even more insane to do to us in Cali or at least knows he's playing with fire.
New York he is lowkey working on a deal with Cuomo (former mayor now running as a spoiler candidate to the socialist who beat him in the primary election).
Chicago is an easier target. The only other city I've heard him float is New Orleans (which is unlike any other city I've been to in the states for its amazing seafood, bars, walkable areas, music, eg culture... notably Black culture)
His mostly rural base loves it. Not only is it cities that they have been other-ing and blaming [insert South Park - They took 'er jobs meme] for their problems their whole lives. It is also abuse of minorities. So it is like saying "you know how you complain about cities and they happen to be brown and black. Im going to fix that problem and it just so happens to be by going after those people who don't look like you. wink wink, nudge nudge"
The Midwest has a weird relationship with Chicago. It's our city dammit, but it's thought of as a shithole because of a long history of it being a shithole and also because of a long history of it being used as a byword for dangerous urban areas. People who hadn't been there in a decade were calling it Chiraq so much that my phone recognized the word. As a teenager (late 00s and early 10s) the far right edgelords would joke about bombing it like they did about Tehran. But it's also a costal city with all the limp wristed elite dogwhistles and homophobia. Which is a little funny because Chicago gay culture is tough as fuck. But yeah and there's the racism which is huge and is an undercurrent of it all.
So yeah it's the Midwest's own Al Capone themed LA, but the sky is trying to kill you not fires and earthquakes.
The Sky is trying to kill you?
Tornadoes, wind storms, idk if Chicago still gets blizzards but they used to…
Chicago is the next city ICE is set up to ramp up operations in. Chosen probably because it is a liberal city with a diverse population.
Chicago is a major democratic leaning city infamous for its association with lawlessness and organized crime. Reality is that Chicago cleaned up with the other cities but it maintains a rambunctious similar to LA and Philadelphia. But it's still got a local culture of early 20th century gangsters like Al Capone and other Italian Americans with submachine guns.
The entire great lakes region that includes Chicago had a pretty rough time from the 70s-00s, with other cities in it including Detroit, Cleveland, Buffalo, and Toronto as well as tiny hellholes of deindustrialization like Gary.
Chicago is also notably a very black city, especially by Midwestern standards. During the great migration (when a bunch of black people left the rural southern areas their ancestors had been enslaved in and went to urban areas largely in the north and west), Chicago was one of the major destinations as there was a lot of work that didn't involve farm labor.
So yeah mocking Chicago sometimes will have racist implications (though this applies to any great lakes city when compared to the overwhelmingly white rural and suburban Midwest).