Yet to have heard Obama's rivals on the presidential campaign trail tell it over the last many months, the two Chicago Democrats have been virtually joined at the hip for years.
Before Obama hit the political big time four years ago, he was largely irrelevant to Daley and even bucked the mayor's perceived interests on occasion without repercussions. For the most part, Daley's interests were more parochial than Springfield or Washington.
While Obama never relied on city patronage workers passing out palm cards, his ascension as an outsider was aided by powerful people who also were key players inside Daley's sphere of influence. And as Obama gained prominence, the interests of the next Oval Office occupant and the current inhabitant of the fifth floor of City Hall have grown closer.
Like many city Democrats in Springfield, Obama's legislative goals often aligned with the mayor's. Obama and others from Chicago supported more money for schools and public works and backed more stringent gun control.
"The mayor's agenda was our agenda as Chicago Democrats in the legislature," recalled state Sen. James DeLeo of Chicago, who served with Obama and is close to Daley.
Still, Obama wasn't afraid to oppose the interests of a powerful Daley family member. In 2003, Obama was one of the few Democrats in Springfield to dare criticize a heavy-handed lobbying drive by the mayor's brother, then SBC President William Daley, that produced a law giving the telecommunications giant a big edge over competitors.
"Ramrodding bills through because you've got the clout to do so—rather than because you've got arguments on your side—is not a good way to do the people's business," Obama said at the time.
Obama's ability to find common ground with the desires of the city's political establishment, while still shaping his reformer image, was an artful dance that speaks volumes about his non-confrontational style and pragmatic approach to change.
It also helped that his political base was the diverse Hyde Park-Kenwood neighborhood, a historical breeding ground for liberal independents who often annoyed City Hall but were tolerated nonetheless.
Abner Mikva, a former state lawmaker and congressman from the same neighborhood, said Chicago power brokers have traditionally expected Hyde Park politicians to be contrarians to the status quo, particularly on issues like ethics reform or racial profiling by police.
"You get a lot of leeway if you're from Hyde Park," said Mikva, an Obama supporter who also served as White House counsel for President Bill Clinton.
Obama is hardly the first liberal Democrat from Chicago to come to an accommodation with City Hall. The late Sidney Yates, who represented a North Side congressional district for nearly a half-century, pursued a reform agenda in Washington while avoiding criticism of machine politics back home.
The late Harold Washington was for years a loyal cog in the Democratic organization as he rose through the ranks from state lawmaker to the U.S. House. It was only during his successful bid to be Chicago's first black mayor that Washington assumed the mantle of a political maverick.
Alton Miller, who served as Washington's press secretary, said it was no surprise that Obama eventually worked with Daley allies who didn't share his reform agenda.
"A legislator has to make compromises in order to be a successful legislator," said Miller, now an associate dean at Chicago's Columbia College. "It's in the job description."
Obama by nature is a cautious but calculating politician, and it wasn't until he was safely in the U.S. Senate and poised to launch his presidential bid that he endorsed Daley for re-election against two African-American challengers. Only two years earlier he had publicly complained that corruption at City Hall gave him "huge pause" about Daley's stewardship.
It is perhaps easy to understand why critics could assume that Daley and Obama have long been cozy. Despite its size, Chicago in many respects is a small town when it comes to politics, and the inner circles of Daley and Obama are inhabited by many of the same faces.
"There are lots of Obama supporters who have both an emotional investment in his candidacy and a financial investment in City Hall," explained one political insider with a foot in both worlds who spoke on condition that his name not be revealed.
The architect of Obama's U.S. Senate campaign and his presidential bid was David Axelrod, the same consultant who has served as Daley's political strategist since 1989. Rahm Emanuel, Obama's choice to be White House chief of staff, began his political life as a fundraiser for Daley.
The common ties even include Obama's wife, Michelle, who had worked for Daley in his executive office and at the city Planning Department years before Obama launched his political career. Daley's planning commissioner at the time, Valerie Jarrett, became a close friend of both Obamas, was a top adviser to his presidential campaign and is now poised to play a key role in the new administration.
Despite Obama's state Senate vote five years ago against William Daley's interests, the mayor's brother also served an advisory role in Obama's campaign and is now a member of the president-elect's transition team.
With Obama's election, he clearly has eclipsed Daley as the most politically powerful Chicagoan. Yet Daley also comes out a big winner.
Daley has been no stranger to presidents, forming tight relationships with both George Bushes and Clinton.
With Obama in the White House, it promises to only get better for Daley. The mayor gains a sympathetic ear to Chicago and its needs. At the same time, Obama can now be scratched off the list as a viable African-American mayoral challenger to Daley.