Obama: Marty Nesbitt
Obama has been close with Marty Nesbitt, a fellow Hyde Park resident and basketball companion, for years. Nesbitt, an entrepreneur, started a successful airport-parking company in Chicago. After serving as the finance chairman of Obama’s unsuccessful 2000 congressional campaign, he's now the treasurer of Obama’s presidential campaign. His fund-raising acumen paid off even before that: In 2002 Marty put Obama in touch with Illinois’ astoundingly wealthy Pritzker family (worth $20 billion) to help with his Senate campaign. But it's not all business between the two; up until the hectic presidential campaign they still played basketball together, went out to dinner with their wives, and socialized within Hyde Park's clique of affluent African-Americans. Marty's wife also delivered both of the Obamas' children (don't worry, she's a doctor), and Obama is the godfather to the Nesbitts' youngest son.

McCain: Bud Day
Former Marine Bud Day nursed McCain back to health in Vietnam, handled his divorce proceedings, and travels with him on the campaign tour. Considered to be the most decorated war veteran since Douglas MacArthur, Day served in World War II, the Korean War, and Vietnam. Day was captured by the Vietcong in 1967 and escaped, but was recaptured just a few miles short of reaching American forces. He spent five-and-a-half years in captivity, where he met John McCain and cared for him in prison. Day advised his friend against running for office back in the eighties, likening politics to prostitution. In 2004, Day aligned with the anti–John Kerry group Swift Boat Veterans for Truth that McCain denounced. In the current campaign, Day woos veterans for McCain.