Welcome! You are now reading the sophomore bulletin 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
On August 28th, 2025 Alderwoman of the 50th Ward of Chicago Debra Silverstein posted “Greetings from Israel. I have been abroad this week as part of a delegation of Chicago and Illinois elected officials.”
The Ministry of Foreign Affairs of Israel generously covered all expenses (including presumably food, lodging, and a business class flight 6,180 miles away from their pesky constituents) for at least 4 Chicago Aldermen to take a 5 day late-August vacation. At least 3 of Ald. Silverstein’s travel companions appear to have insulted the generosity of their Israeli Hosts by failing to publicly express gratitude for the experience.
Discourtesy doesn’t sit right with us here at SILLY PRIZES, the third or fourth favorite blog of modest Chicago political wonks of all stripes. As this outlet’s humble author and with my tongue planted firmly in cheek, I would like to deeply apologize to the State of Israel on behalf of the following Chicago Aldermen for their lack of public acknowledgement over the past two months of the generosity you provided to them earlier this year:
42nd Ward Alderman Brendon Reilly
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