In the Chicago Tribune, Ambivalence of hopes it states:
Obama and the rest of Chicago's powerhouse delegation, which included first lady Michelle Obama, Mayor Richard M. Daley and his wife Maggie and the Queen of All Media Oprah Winfrey, were fighting an uphill battle all along.
Expectations were overinflated by the media hoopla. But as the final bidding indicated, the IOC has a mind of its own.
Speculation runs wild as to why Chicago lost. Most of it follows personal agendas. The negatives that various analysts and critics bring up -- crime, corruption and cronyism lead the pack -- are hardly unique to Chicago and are certainly no worse than the problems faced by Rio de Janeiro, the winner of the 2016 Olympics.
Rio took an edge in less tangible ways. Chicago's presentation to the IOC, despite the Obama glitter, was lackluster and disorganized compared to Rio's colorful and passionate presentation.
Brazil played the geopolitical card skillfully, holding up maps that showed South America to be the only region left without a single Olympics. This may have touched the hearts of IOC members, who like to think of the organization as a groundbreaking force for international development and unity.
And how savvy, for Brazilian President Luiz Inacio Lula da Silva to use a certain Chicagoan's famous slogan when talking to reporters to promote his country's bid: "Yes we can!"
Which really points out the truth as to why Chicago didn't get it, even the power of Obama was not enough to combat a poor presentation....Or maybe they just didn't like Oprah...