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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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Financial advisors continue to urge consumers to view sports wagering strictly as entertainment and to only risk funds they can afford to lose.

Research from Stanford University published in April concluded that sports bettors remain “overoptimistic,” generally expecting to break even despite losing an average of 7.5 cents on every dollar wagered.

“Overoptimism is largest among bettors who partake in a complex type of bet known as a parlay,” the Stanford researchers wrote. “Compared to other forms of betting, parlays are more likely to be driven by bias.”

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More recently, Polymarket has paid top dollar for prominent athletes and celebrities to promote its prediction market. The company’s paid partners include LeBron James, Derek Jeter, Eli Manning, Spike Lee, and Craig Robinson.

The Polymarket water tower can be seen from I-94, but isn’t overly prominent, as the interstate passes beneath three bridges—Concord Avenue, train tracks, and a service road—near the Mount Elliott exit.

But the advertisement is still garnering plenty of attention online and in the news, with the controversy surrounding the Polymarket branding a major topic of discussion in prediction market and gaming circles.