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Grasso was quick to defend Rovito following his arrest, describing him as “a stellar corporate and residential citizen” who has “a YouTube following of a quarter of a million people or something like that.”

Rovito, meanwhile, was such a fan of the mayor that he named a dish after him— “Linguini alla Mayor Grasso”—a pasta that comes with “fresh tomato sauce and basil, tossed with a touch of olive oil, and topped with fresh ricotta.”

In an op-ed for the Chicago Tribune in June, Grasso complained that “some members of the Chicago news media stigmatize Italian Americans as Outfit members or mafia operatives whenever it serves to embellish a story.”

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The American Gaming Association estimates that the exchanges have siphoned more than $1.3 billion in would-be tax revenue from states. One of the AGA’s primary spokespeople pin its fight against prediction markets is former New Jersey governor Chris Christie, who championed the PASPA case to the Supreme Court.

As with PASPA, this matter revolves heavily around federalism versus states’ rights. Traditional sports betting is governed by individual state regulators with varying laws and regulations. Federal derivatives are regulated by the CFTC, which has fully embraced prediction markets under US President Donald Trump after rejecting them in previous administrations.

The web of lawsuits and court rulings involving prediction markets has greatly complicated the issue of jurisdiction. Kalshi has been forced to limit trading in multiple states, most notably Nevada, and the CFTC has gone to unprecedented lengths to protect its licencees. This includes suing nine states directly and issuing emergency orders to reject state mandates.

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Meanwhile, on a post that received 1.2 million views, Manning joked: “Might have to put the pads back on.” It prompted Sherman to retort, “now let’s try this on the field”, in reference to the prediction market app.

The 2026 NFL season arguably marks the most contentious battle to attract customers interested in sports betting and predictions, dating back to the historic PASPA decision. For the first full NFL season, traditional sportsbooks such as DraftKings will offer sports-event contracts in the three most populous US states – California, Texas and Florida.

Unlike regulated sportsbooks, prediction markets allow customers between the ages of 18 and 21 to trade on sports-event contracts. Craig Carton, a sports talk host with WFAN 660 AM in New York, criticised the athletes for their endorsement of Polymarket. Carton, a recovering compulsive gambler, opined that the “unregulated” gambling markets are driving Americans into bankruptcy and kids out of school. Regulated books prohibit those under 21 from betting on their platform, leading Carton to question the celebrities for promoting the company.