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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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The company only began sales towards the end of 2025, but Yashin says it has subsequently signed around 30 to 40 contracts. Partners include BGaming, SoftSwiss, 1xBet, 01.tech, and Broadway.

Despite his experience launching businesses, Yashin has been surprised by the enthusiastic reception from the wider industry. Perhaps even more revealing is the feedback from the people tasked with selling the product. According to Yashin, one Swipe Games business development manager with more than 20 years’ industry experience told him he had never found a new product easier to pitch.

The response extends to potential customers. Yashin says that of around 50 leads generated through events and the company’s network, only one decided against integration, leaving Swipe Games prioritising a queue of prospective partners.

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In response to a query from local news outlet Patch, Republican Mayor Gary Grasso confirmed the existence of the donations from the Capri restaurant and the Are We Live nightclub, two Burr Ridge businesses owned by Filippo “Gigi” Rovito.    

Rovito, whom NBC Chicago previously reported has alleged ties to the Chicago Outfit, is facing federal charges of operating an illegal gambling business and conspiracy to collect extensions of credit by extortionate means.

He was among 22 people arrested in coordinated raids by the FBI April 29 following a long-running investigation dubbed “Operation Porterhouse Parlay,” which allegedly uncovered links between illegal gambling operations and restaurant networks spanning Northwest Indiana and suburban Chicago.