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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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Also, Stephen Cloobeck, a billionaire and 2026 California gubernatorial candidate, purchased approximately $10,000 in contracts tied to his campaign. He was fined $31,770 and suspended for three years.
Each settlement involved cooperation with Kalshi’s investigation.
What distinguishes Santos’ penalty is the exchange’s allegation that he actively issued false or misleading statements to alter prices and profited materially, violating additional rules such as failure to cooperate and manipulative conduct.
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“There’s this huge, proven revenue opportunity, but it’s also about continuity of the brand that exists across the whole platform and the whole offering,” Wilson adds.
Even the most flexible technology cannot do all the work itself. Wilson is blunt about what happens when an operator treats an integration as the end of the job.
“If I just give you one of our games or our jackpot engine and you just plug it in and leave it there to collect dust, you will come back and tell me in three months’ time it’s not working,” he says. “And I will say to you, ‘How have you invested in the product?’”