Welcome! You are now reading the inaugural dispatch from SILLY PRIZES: a new blog on Chicago Politicians and the silly games they love to play. A bi-weeklyish newsletter by Bebo, current Chicago Rat Czar [citation missing] and former Treasurer of the Chicago DSA PAC (‘22-’24), SILLY PRIZES will dive deep into niche municipal topics, provide quarterly fundraising updates for City Council, and in rare cases like today: may even break a piece of news. Thank you for reading. -Bebo
34 Chicagoans.
Exactly 34 Chicagoans have made financial donations to the ChicagoRED PAC since its inception in March 2024.
For the uninitiated, ChicagoRED is one of two notable groups of Black MAGA Chicagoans who have found time for the past two years to show up at every City Council meeting to do 3 things: recite xenophobic remarks towards migrant arrivals, attack the mayor or his allies, and praise Trump. Chicago Flips Red, the second group, currently lacks any registration of a political entity with the Illinois State Board of Elections and will have to be the focus on a later investigation.
Normally, I cannot tell you an exact amount of PAC donors; that’s true in this case as well. ChicagoRED PAC did us the courtesy of telling us themselves and I’m not sure they’re even aware of that fact.
Illinois Campaign Finance law explicitly states that no political committees are required to itemize donations from donors who give less than $150 to a unique political committee during each quarterly reporting period. This is to everyone’s benefit — small dollar donors maintain an element of privacy and Treasurers avoid work I personally classify as ‘juice not worth the squeeze’.
If 10 people are donating $20 each monthly to their Aldermen, then the Alderman’s political committee can lump those all together as “non-itemized” contributions when they report those figures in a single lump sum to the Illinois State Board of Elections each quarter. In my previous example, $600 of their donations could be listed as “non-itemized” (10 × 3 × 20 = $600)
This makes enumerating an exact amount of donors impossible under normal circumstances because you cannot accurately perform the process in reverse and provide an answer with certainty due to various ways one COULD arrive at $600. To drive the example to its most extreme, perhaps 600 people gave merely $1 each — highly unorthodox but not a technical impossibility and thus unable to be ruled out.
This is one of several key features to Illinois’s Campaign Finance system that is spelled out in remarkably clear language and routinely cited in documentation provided by the Illinois State Board of Elections to all Officers involved in running a PAC, but seems to have eluded the President’s favorite Chicagoans.
P Rae Easley (pictured left) is the current chair of the ChicagoRED PAC
Unaware or unconcerned with this nuance, officers for ChicagoRED PAC would itemize all 174 unique donations on physical paperwork, effectively doxxing every last one of their roughly 145 unique donors in publicly available findings.
On October 16, 2025 the ChicagoRED PAC would file 6 quarterly reports to the Illinois State Board of Election, after receiving notice of a $9,500 fine due to a lack of filing regular quarterly reports with the board in the previous month of September.
Eschewing my beloved IDIS electronic filing system, ChicagoRED PAC filled these reports out with pen and paper – delaying, but not killing my ability to analyze their reports until a few days ago when the scans of their physical paperwork were finally uploaded to the SBE database.
Turns out that the $9,500 fine threatens to consume every last dollar they had ever raised, as their total contributions since the PAC’s inception in March 2024 only amounts to $9,362.70.
Here are some key figures discovered in my analysis:
All data below is current as of 9/30/2025
Total Raised: $9,362.70
Unique Contributions: 174
Unique Donors: 145
Out of State Donors: 92
Total Raised from OoS Contributions: $6,613 or 71% of all funds raised
Illinois, but not Chicago Donors: 19
Total Raised from Illinois, but not Chicago: $769, or 8% of all funds raised
Chicago Donors: 34
Total Raised from Chicago Contributions: 1,979.90 or 21% of all funds raised
Retiree Donors: 66
Total Raised from Retiree Contributions: $2,481.50 or 27% of all funds raised
Current Cash on Hand: $0.46
Perhaps most alarming for the future of ChicagoRED PAC is the revelation that the President’s so-called “Golden Age” might have catapulted him into billionaire status, but it has been profoundly unkind to his supporters: 84% ($7,886) of all lifetime donations received came in prior to January 1 2025 and in the interim they’ve only raised a paltry $1,477 through the end of September 2025.
Despite now having filed their reports, they are far from out of the woods here: their $9,500 fine is still applicable and their filings reveal further compliance issues which will soon become an issue for them.
Perhaps the single largest fucky-wucky they have made here is disclosing that they accepted a $3,000 donation from a Californian last year. Normally any donation exceeding $1,000 has to be reported publicly within 5 days, and that shrinks to a scant 48 hours in the heat of election season.
I crunched the numbers: they kept this donation hidden from the people of Chicago for 303 days, exceeding their allotted time to report this donation by OVER 60 times. This is a remarkably egregious, seemingly willful, and repeated violation of the black and white letter of the law. Fines for these violations could reach up to 150% of the violating contribution, adding another possible $4,500 in fines that the Illinois SBE could force them to pay up in restitution.
A Silly Prize of $14,000+ in fines looms on the horizon for the President’s favorite Chicagoans.
They have no money in the bank.
They are really struggling to fundraise.
They just exposed all of their donors’ private information due to sheer incompetence.
As the one-time financial steward of >$63K for Chicago DSA PAC for nearly two full years without receiving a single reprimand from the SBE, I can confidently say: ✨skill issue✨
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