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I don't have any suggestions, I'm sorry. It's something you hear about from other people who have lived here longer and just kind of observe happening to you and around you through daily life, the news, and Wikipedia rabbit holes. My favorite depiction of the Machine is in the show South Side. I have no idea how true to life it is, but they capture the spirit of Chicago politics really well.

Lol back in 2019-2020, I volunteered with Marie Newman's campaign. She was a progressive Democrat running for the House of Representatives, Illinois District 3, as a challenger to the incumbent Dan Lipinski (also a Democrat, but a socially conservative blue dog Dem, so he voted against things like abortion and health care). Here's the thing about Dan Lipinski: he basically inherited the position from his father and kept it for seven terms. How does that work? Rep. Bill Lipinski ran for re-election in the Dem primary, won it, and then retired. He talked the IL Democratic Party into replacing him with his son on the election ballot. Here in northern Illinois (I don't know how far the political machine reaches out from Chicago), the dem races are the only races because nobody up here votes republican. (Sidenote: Chuy Garcia, a progressive Representative from IL-4, got reprimanded last month for doing something similar: on the day of the deadline to register for the ballot, he waited until there were only a few hours left and announced his retirement. His chief of staff stepped forward as the only Dem eligible to register because she had already collected all the signatures she needed.)

With that background in mind, let's get back to my anecdote! I was volunteering for this upstart campaign and I come into the office to all this chatter one day. It was a week or so until the primary, and even busier than expected, so I asked another volunteer what was up. They were trying to catch up on stuff they'd had planned for the previous day, when they'd been unable to work because someone from Lipinski's campaign physically cut power to the office. If I remember correctly, the power cut was only to the section of the building where Newman's campaign office and a couple others were, the kind of disruption that took some research to pull off. A breaker getting flipped could've been fixed in minutes, maybe an hour if it took that long for someone to go and check it. The power line was cut and getting a line worker to do the repair took them the whole day. Despite the Democratic machine's best efforts, Newman won the seat. She held it right up until 2023, when they gerrymandered it out from under her.

You do not defy the Machine.