City officials and the Chicago 2016 Olympic bid committee are ramping up their campaign. Just a little over a year from now the International Olympic Committee will convene in Copenhagen to decide on the host city, and between now and then Chicago has to convince the world that it not only has the money and infrastructure to host the games but that its citizenry supports the effort.

In 2004, when Frayne was a thermal engineering manager in California’s Silicon Valley, he explains, he watched controversy unfold over New York City’s ultimately unsuccessful bid for the 2012 Olympic Games, as residents voiced concern over the potential for overzealous use of eminent domain, displacement, and diversion of funds from more urgent city improvement projects. But he was disappointed, he says, that there was no centralized forum where the public could discuss those issues. This, he says, inspired him to buy up more than 40 domain names—”as many as I could afford,” Frayne says—including Tokyo2016.com, Chicago2016.com, LA2020.com, NYC2020.com, and Moscow2024.com; he won’t say why he chose the combinations he did or how much he paid for them. Frayne was betting that at least one of his city-year combos would end up short-listed by the IOC, and so far two have: Chicago 2016 and Tokyo 2016. Four days after he registered Chicago2016.com, the city, considering a bid, registered Chicago2016.org.

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This has happened with Olympics Web sites before: Web hosting company and domain registrar GoDaddy registered Athens2004.org and used it to redirect visitors to several other sites, including one that offered online gambling, and Network Solutions LLC registered Beijing2008.org but didn’t put any content on the site. When the respective Olympic committees filed complaints, neither company fought them.

When the two met on November 14, 2007, Frayne says, he told Stiers he had no interest in selling. But Stiers says Frayne also asked how much traffic Chicago 2016 was getting on its .org site and how much the committee would value the .com site. Frayne said he would hold on to the site until Chicago won the 2016 games and then “study his options,” according to Stiers.

In early June, Frayne says, Patrick Ryan, the Chicago businessman who chairs the Chicago 2016 committee, called him to set up a meeting. “He also informed me that he’s the chairman of Northwestern’s board of trustees,” says Frayne, who’s in his second year at Kellogg. “He just wanted to make sure that I knew that.” Patrick Sandusky, a bid committee spokesman, says that’s not true. “Patrick never spoke with him,” Sandusky says.