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It's the first time in more than a year of crisscrossing the country that the real-estate mogul has spoken directly to African-Americans at large, and asked for their support.
Trump's strategy for luring black voters into his orbit involved mocking their schools, denigrating their neighborhoods, and citing inaccurate statistics on the impact of youth unemployment.
All of those points were bookended with phrases like, "What the hell do you have to lose?", "You'll be able to walk down the street without getting shot," and "Give Donald Trump a chance."
On Saturday, the Manhattan billionaire took news about NBA champion Dwyane Wade's family tragedy and turned it into the equivalent of a campaign yard sign:
Prominent black voices throughout the country have scolded Trump's outreach methods, calling them tone-deaf and out of touch.
"I hear him not talking to black people, but talking to white people about black people so they will think he cares about black people," former Atlanta newspaper publisher Alexis Scott told The New York Times in a story published on Wednesday.
Marc Morial, the president of the National Urban League, agreed, telling The Times: "Black America has deep problems ... but black America also has a large community of striving, successful, hard-working people: college educated, in the work force."
AP Photo/Mark J. Terrill
Former GOP presidential candidate and Trump surrogate, Dr. Ben Carson, was similarly unmoved by Trump's strategy - which included calling Hillary Clinton a "bigot."
In an interview with The Daily Beast, the world-renowned neurosurgeon commented on the name-calling: "That's what people do who don't have anything to talk about," he said.
Harvard University professor, Jennifer Hochschild told Reuters that Trump's efforts are all but useless, despite his assertions that he can improve the economic outlook of black voters.
"General cluelessness about racial dynamics will diminish any possible black support that comes from Trump's emphasis on job creation," she said.
As the fall debates draw near, Trump continues to poll in the single-digits among African-American voters.