Republican White House hopeful Mitt Romney ventured into the heart of Barack Obama's support base, drawing loud boos from African-Americans when he vowed to repeal the president's health care reforms.
Romney's address to the National Association for the Advancement of Colored People (NAACP), America's oldest and largest civil rights group, was billed as a brave appeal to a voting demographic that overwhelmingly favors his opponent, the first black US president.
It was certainly a tough crowd and some cackled when the presumptive Republican nominee declared: "If you want a president who will make things better in the African-American community, you are looking at him."
Polite applause for his pro-jobs pitch was accompanied by some raised eyebrows when he said Obama had left the economy "worse for African-Americans in almost every way."
But he ran into what was perhaps the most negative reaction to anything he has said on his year-long White House campaign when his pledge to repeal the Affordable Care Act was met with loud and sustained boos.
"I think we expected that of course, but you know I'm going to give the same message to the NAACP that I give across the country," Romney told Fox News hours later.
"Obamacare is killing jobs and if jobs is the priority then we're going to have to replace Obamacare with something that actually holds down health care costs, as opposed to causing more spending for the government and more spending for American families."
Blacks voted overwhelmingly for Obama over Republican John McCain in 2008, but with US unemployment above eight percent for 41 straight months and a recent spike up to 14.4 percent jobless among blacks, Romney aims to win over disaffected voters.
The NAACP jeers exposed the uphill battle he faces in convincing minority voters he is the best man for the White House.
Wednesday marked a sensitive time for health care, with the Republican-led House of Representatives doing Romney's bidding and voting to repeal the law, although the effort is all-but certain to fail in the Democratic-led Senate.
In his speech, Romney addressed the need to curb government spending. "To do that I'm going to eliminate every nonessential expensive program that I can find," he said. "That includes Obamacare."
Before he could finish his sentence, the boos rained down loudly, lasting more than 20 seconds.
While it was an awkward moment to be sure, it was also seen as courageous of the Republican to stand before a pro-Obama crowd and sell his political platform. Supporters took to Twitter to praise his determination.
But NAACP president Benjamin Jealous said Romney's repeal pledge showed a "fundamental misunderstanding of the needs of many African-Americans," millions of whom stand to benefit from health care reform.
The former Massachusetts governor argued that Obama's presidency, while historic, is leaving many black families behind.
"If equal opportunity in America were an accomplished fact, then a chronically bad economy would be equally bad for everyone," Romney said.
"Instead, it's worse for African-Americans in almost every way. The unemployment rate, the duration of unemployment, average income and median family wealth are all worse for the black community."
Romney said he was confident his policies "will help hundreds of millions of middle-class Americans of all races" and lift people out of poverty.
He also argued that the Obama camp was telling Americans that Romney was "running for office to help the rich.
"Nonsense. The rich will do just fine whether I am elected or not," he said. "I want to make this a campaign about helping the middle class."
Blacks are expected to back Obama in November, but the question in a neck-and-neck race is whether Romney can lure enough black voters to make a difference in swing states like Florida and North Carolina.
McCain won just five percent of the black vote, and Romney is aiming to bring the figure closer to the 11 percent that George W. Bush won in 2004.
His NAACP address can be seen as an effort to make Romney, a multimillionaire ex-businessman with a reputation of not connecting with everyday voters, appear more attractive to a diverse electorate.
He has a daunting task. Republican-led efforts in several states to require voters to present government-issued ID at polling stations is seen as having a disproportionate effect on minorities and the poor, who vote more Democratic.
And he wants Bush-era tax cuts extended for all Americans including the rich, a position that might not sit well with working-class voters.
Vice President Joe Biden addresses the NAACP on Thursday.