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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.

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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.”

Federal prosecutors, however, do not mention the mafia in court documents. They allege the gambling ring generated millions of dollars through illegal sports betting, video gambling, and loansharking operations, with members using intimidation and violence—or the threat of it—to collect debts.  

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In a separate case, the ASA examined display advertising for White Hat Gaming’s Casimba and The Grand Ivy Casino brands, which had appeared on HLTV.org – a specialist Counter-Strike 2 e-sports website – in March 2026.

Two banner ads promoted a “100% match bonus up to £100 on 1st deposit” and displayed the mandatory 18+ logo. The ads appeared alongside live match coverage featuring betting odds and sponsor logos, including a link to Casimba’s website. 

A complaint suggested that such placements were inappropriately targeted at under-18s.