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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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Shortly after his release, Santos had begun working as an influencer for Polymarket.
Santos’ case represents the most severe among four disciplinary settlements announced by Kalshi, which has faced increasing scrutiny concerning insider knowledge risks and event outcome influence by market participants.
Santos is not the only individual disciplined for trying to game the prediction market system. Ben Midgley, a Republican candidate for the governorship of Maine, admitted purchasing under $1,000 worth of contracts related to his campaign. He accepted a $5,434.30 fine and a three-year suspension.
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Beginning with the US presidential elections in November 2024, when prediction markets catapulted into mainstream culture, their rise has been undeniable. Kalshi and Polymarket have seen their valuations balloon to $40 billion and $21 billion, respectively, and the majority of the top US bookmakers have scrambled to expand into the prediction space in various forms, either by building their own exchanges, acquiring existing ones or engaging in market-making.
Commercial sports betting generated just under $17 billion in nationwide revenue in 2025, which is why Davenport asserts that the “stakes of this case are exceptionally high”. Kalshi and Polymarket alone posted more than $45 billion in trading volume, which is similar but not identical to betting revenue, in August. That was a 15% decline from July, although that drop is attributed to the conclusion of the Fifa World Cup tournament that month per Yahoo! Finance.
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.