Navigating Chicago's Casino Deal: Financial Complexities and Tax Implications

In today’s episode Patrick McKenzie (@patio11) examines a Chicago casino investment, first of its kind within the city limits. Patrick reads from his Bits About Money essay (published January 2025) with additional commentary based on recent developments. The discussion reveals how municipal politics, grievances about national and local economic history, and creative financing intersect for ‘a very Chicago gamble.’ 

–

Full transcript available here:
www.complexsystemspodcast.com/the-landmines-buried-in-the-fine-print-of-chicagos-new-casino-deal/

–
Sponsors:  Safebase
 

Ready to save time and close deals faster? Inbound security reviews shouldn’t slow down your team or your sales cycle. Leading companies use SafeBase to eliminate up to 98% of inbound security questionnaires, automate workflows, and accelerate pipeline. Go to safebase.io/podcast 

–

Links:

• Bits About Money: https://www.bitsaboutmoney.com/archive/chicago-casino-investment-offering/ 
• The Story of Vaccinate CA: https://worksinprogress.co/issue/the-story-of-vaccinateca/ 
• The Conservative Investor: https://www.patreon.com/theconservativeincomeinvestor 
• Complex Systems interview with Jim McKenzie: https://open.spotify.com/episode/6ocJirzGTStuf0K9ITM21X?si=7HA0RhEOS8GFsA1MlY-EVw

–

Twitter:
@patio11

–

Timestamps: 
(00:00) Intro
(01:43) Chicago has wanted a casino for a long time
(04:55) The stock offering
(10:29) Chicago’s peculiar definition of minority
(14:04) Sponsors: Vanta | Check
(16:26) Reading a complex corporate structure
(20:29) Is this valuation a gift to investors?
(23:20) Capital stack arbitrage
(30:04) The casino will not distribute profits, per se
(32:45) Tax consequences of this offering
(38:34) In conclusion