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The relationship has drawn additional attention since Rovito’s arrest.
In June, Grasso wrote an opinion piece in the Chicago Tribune criticizing what he described as media coverage that unfairly associates Italian Americans with organized crime. However, he did not directly name Rovito in the piece.
“I’ve sadly watched some members of the Chicago news media stigmatize Italian Americans as Outfit members or mafia operatives whenever it serves to embellish a story,” Grasso wrote.
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Polymarket has developed its media presence elsewhere. In January, it signed a deal with Dow Jones to provide its prediction market data to several of the publisher’s consumer platforms. The deal covers publications including The Wall Street Journal, Barron’s, MarketWatch and Investor’s Business Daily.
Prediction markets have become more and more intertwined with sports and entertainment businesses. Polymarket has agreements with Major League Baseball and Sportsradar. Sportsradar provides data and services for more than 20 sports leagues and competitions.
The company has also pursued partnerships outside the normal financial media. Its deals include relationships with major sports organizations and entertainment properties, signaling efforts to integrate prediction markets into mainstream content and information services.
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Friday’s announcement followed an investigation that found he manipulated contract prices linked to his anticipated attendance at the 2026 State of the Union address.
He was also fined $71,356.
Kalshi’s compliance department uncovered a series of large trades made by Santos throughout February 2026 involving contracts that would pay out based on whether he attended the State of the Union address on 24 February.
