After days of speculation, NAACP's Cornell William Brooks told CNN that Trump had declined the group's invitation to address its members in Cincinnati at their conference, which is being held this weekend.
Hillary Clinton, the presumptive Democratic nominee, is scheduled to speak, Brooks told CNN's Wolf Blitzer on "The Situation Room."
"Mr. Trump has declined our invitation, so we will hear from Sec. Clinton," Brooks said. "Namely, the explanation given was that (the Republicans) are holding their convention at the same time. We are, of course, in Cincinnati, they are in Cleveland. We were hoping he would make the short trip from Cleveland to Cincinnati."
The Trump campaign did not immediately respond to a request for comment.
Trump's decision to skip the event represents a change of course from previous Republican presidential candidates, with 2012 GOP nominee Mitt Romney addressing the 103rd NAACP annual convention in Texas.
Brooks said he was disappointed by Trump's announcement, saying it was a missed opportunity for the real estate mogul to respond to recent problems between law enforcement and the African-American community.
"I will simply say this: the NAACP, representing millions of Americans, we represent an occasion for those running for president to speak to the nation's most critical issues at a critical hour in this country," Brooks said. "You can't run for president and not talk about police misconduct and police brutality. You can't run for president and not talk about this country's civil rights agenda, so this is an important moment and our convention really will be an opportunity for anyone running for president to provide a window into not only their policies, but into their heart and character as a candidate."
Asked by Fox News' Bill O'Reilly if he is able to understand the black community, Trump said: "Well, I'd like to say yes but you really can't unless you're African-American. Because I do understand what goes on in life, and I do understand that the economics of our country are not the same ... that our educational system stinks, it's absolutely horrible."
"We need a cheerleader, not a divider," he said. "We have a divider as a president. (Black Lives Matter) are certainly dividing America."