Well degenerates, welcome to the final dumpster fire of 2025. Just hours before the ball drops, a coalition of gambling giants is scrambling to stop Chicago from picking their pockets.

The Quick Hit

• What happened: DraftKings, FanDuel, BetMGM, Bet365 and Fanatics are suing the City of Chicago
• The damage: A new 10.25% tax on sports betting revenue kicks in at midnight
• Why you should care: Your favorite sportsbooks might shut down in Chicago tomorrow
• The move: If you're a Chicago degen, maybe get your bets in before the clock strikes twelve

The Lawsuit Breakdown

The Sports Betting Alliance dropped the legal bomb on Monday, filing for a temporary restraining order in Cook County Circuit Court. Their argument is pretty straightforward: Chicago can't just make up its own gambling taxes whenever it needs to patch a budget hole.

According to the lawsuit, the Illinois Constitution reserves authority over gambling taxes to the state government. Chicago, they claim, is basically pulling a power move it doesn't have the authority to make. The city "hastily enacted" this tax as a last-ditch effort to balance its budget before the December 31 deadline.

And here's the real kicker that has operators losing their minds: despite every assurance from the city that new licenses would be issued by December 29, not a single operator has received theirs. The new rules require these licenses to operate legally, which means if everything goes into effect tomorrow as written, your sportsbook apps might just go dark.

What Chicago Wants From Your Action

Let's break down what the city is trying to squeeze out of this:

• 10.25% tax on gross gaming revenue
• $50,000 upfront master license fee
• $25,000 annual renewal
• Additional $10,000 platform provider fee
• $5,000 platform renewal fee

Keep in mind, these operators are already paying between 20% and 40% in state taxes, plus per-wager fees of 25 cents on each of the first 20 million bets and 50 cents after that. Chicago essentially looked at that and said "we want some too."

Why This Matters to Your Bankroll

If you're betting from Chicago right now, you should probably pay attention. The Alliance isn't bluffing when they say operators might have to shut down rather than operate illegally. No licenses have been issued. The tax takes effect in hours. Something has to give.

The smarter play here is watching how this unfolds. If sportsbooks do pause operations, it's probably temporary. But the chaos of figuring out open bets, pending withdrawals, and account access could be a headache nobody needs while nursing a New Year's hangover.

The Bottom Line

Chicago politicians tried to sneak a gambling tax through in the final moments of budget negotiations, and now they're getting dragged to court for it. Whether the restraining order comes through in time is anyone's guess. Either way, the first day of 2026 in Chicago sports betting could be very interesting, or very quiet. Get your action in tonight just in case, and maybe pour one out for whatever intern has to sort this mess out on January 2nd.