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Prosecutors charged him with operating an illegal gambling business and conspiracy to collect extensions of credit by extortionate means. The indictment alleges that the operation involved sports betting and the collection of gambling debts.

Rovito has pleaded not guilty and is presumed innocent unless proven guilty in court. His attorney has disputed the government’s allegations, claiming that the indictment does not allege his client collected money, made any threats, or directed other defendants to do so.

The latest contribution is not the first time Rovito’s campaign donations to Grasso have attracted attention.

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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 charter does not create new regulatory obligations and was designed to complement legislation including the EU AI Act and GDPR.

Instead, it proposed a risk-based approach. It suggested lighter controls on use cases such as coding assistants, but strong checks on customer-facing functions, particularly those involving fraud and responsible gambling.

Kenneth Brincat, CEO of the MDIA, said companies needed “practical ways” to better understand where AI fits within their businesses.