Sen. didn't have to issue the challenge about homophobia in the African-American community - not in one of the nation's premier black churches, not on the eve of the Martin Luther King Jr. holiday - but he did it anyway.
"If we are honest with ourselves, we'll acknowledge that our own community has not always been true to King's vision of a beloved community," Obama told 2,000 worshippers Sunday at Atlanta's Ebenezer Baptist Church, where King once preached. "We have scorned our gay brothers and sisters instead of embracing them."
The statement drew polite applause from the congregation, but it roared across the gay blogosphere, earning almost universal praise from a constituency that doesn't always feel supported by presidential candidates.
Yet the goodwill - at least among some in the gay community - evaporated quickly.
At the same time as Obama's Sunday speech, gay bloggers were digging into the background of the Rev. Kirbyjon Caldwell, a spiritual adviser to President Bush who endorsed Obama a day earlier. They turned up a page on his Houston church Web site promoting a ministry to cure homosexuals, sparking outrage among the same bloggers who were extolling him only a few hours earlier.
The twin developments appeared to encapsulate the tension inherent in Obama's embrace of what he calls a new style of politics, his belief in forging alliances even with those who hold fundamentally different views.
In this case, he has spoken out against homophobia in front of black audiences while embracing some black religious leaders who are resistant to gay rights.
"People are confused," said Wayne Besen, a gay activist and founder of Truth Wins Out, a New York organization aimed at countering the "ex-gay" movement. "We see one report of him saying powerful words. Then he is hanging out with some shady characters. People don't know what to make of that."
By Monday, Caldwell's church, Windsor Village United Methodist in Houston, scrubbed its Web site of any reference to the gay conversion program, Metanoia Ministry.
In a Politico interview Tuesday, Caldwell said his 14,000-member church - one of the largest United Methodist congregations in the country - is not affiliated with Metanoia.
"I got to tell you, this is going to sound real stupid, but I didn't know it was on our website," Caldwell said. "I was surprised and embarrassed by it. I'm embarrassed from the standpoint that I should have known. We have 120 ministries at the church. You can't be on top of everything."
When asked if he opposed such programs, Caldwell said: "It's not a ministry of the church. It is not supported financially by the church. It is not located at the church. That is pretty much where I am with it."
Caldwell issued a similar statement Monday to John Aravosis at Americablog, a a popular liberal website.
But blogosphere skepticism has persisted, in part because of this connection: Barbara Hicks, a church staff member and treasurer of the church's Prayer Institute, is listed as the contact for Metanoia Ministry. She uses a church phone number and email address.
"That is my ministry," Hicks said Tuesday when reached at her church office.
She directed further questions to Caldwell, who said Hicks "does it on her own."
The controversy started Saturday when Caldwell told Texas reporters that he was personally backing Obama for his "character, confidence and courage." He said he would campaign for the Illinois senator, who might even appear at the church.
But two days later, the Obama campaign, which did not participate in the endorsement, appeared to back away from Caldwell.
The campaign told Americablog on Monday that Caldwell has not - and will not - be asked to do anything for the campaign. In a statement posted on the blog, Caldwell said neither Obama nor his staff "knew of this outside ministry, nor have they expressed any agreement with my church's belief on gay rights."
"Bottom line: Obama gets some major chits for what he did yesterday morning, and with that in mind, I think on this one we can give him a pass," Aravosis wrote Monday.
Aravosis was highly critical of Obama in October for appearing with Donnie McClurkin, a gospel singer who considers himself an "ex-gay" and has called homosexuality a "curse." Obama and McClurkin traveled South Carolina as part of a gospel tour aimed at religious African Americans.
Besen, who was also vocal during the McClurkin controversy, said Obama "deserves a lot of credit" for his speech, but was not as forgiving about Caldwell.
"It matters who you are endorsed by because these are the people who are going to be calling in favors," Besen said. "The gay and lesbian community has the right to be disturbed when such individuals are standing up beside Obama."
For his part, Caldwell said he is a "believer in everybody having access to all rights and privileges."
When asked if that meant he supported civil unions and gay marriage, Caldwell said: "I would need to check with the church."