"At the end of four years, I guarantee you I will get over 95 percent of the African-American vote. I promise you," Trump said to a largely white audience Dimondale, Mich., a town where in 2010 just 9 of the town's 1,234 residents were black, according to census data.
He began by extolling the contributions of African-Americans.
"The African-American community has given so much to this country. They fought and died in every war since the Revolution. They've lifted up the conscience of our nation in the long March towards civil rights. They've sacrificed so much for the national good.”
But then he painted an exceptionally grim picture of the African-American community, describing black voters as largely impoverished and unemployed.
"You're living in poverty, your schools are no good, you have no jobs, 58 percent of your youth is unemployed, what the hell do you have to lose?" Trump asked, repeating a question he posed to his crowd in Charlotte, NC Thursday night.
Some bristled at the implication that most African-Americans were impoverished or not well educated. According to Census Data from 2015, 52.9% of all Black Americans aged 25 or older hold some sort of college degree. A Pew report released in December shows that black adults experienced the largest income increase from 1971 to 2015 and were the only racial group to see a decrease in the percentage of their low-income earners.
As a whole, however, black Americans face huge wealth disparities when compared to white Americans that many experts attribute to years of systemic discriminatory practices such as segregation, housing discrimination and failing schools.
As Trump tries to attract black voters, the ability to attract such a high level of support in four years would require a major turnaround from Trump's current poll numbers.
In President Obama's two victorious campaigns in 2008 and 2012, he attracted 95 and 93 percent support within demographic, respectively. The Democratic candidate for president has won at least 82 percent support from African-American voters in every election since 1972.
In addition to his dismal poll numbers, Trump also faces other challenges in attracting black voters. Trump was the public face of the Birther movement, accusing President Obama, without any evidence to support his claim, of being born outside the United States. Obama is a natural-born citizen.
Trump and his father were sued in the 1970s, accused of housing discrimination and intentionally excluding blacks and Hispanics from becoming tenants in his building. The case was brought by the Department of Justice for alleged violations of the Fair Housing Act, and both parties settled in 1975.
According to the New York Times, Trump initially called the claims "ridiculous" and the settlement did not include and admission of wrongdoing.
And, as his campaign was in its nascent stages, Trump retweeted a graphic loaded with racially charged and incorrect statistics on black-on-black crime. Trump recently hired Celebrity Apprentice star Omarosa Manigault as the campaign's Director for African-American outreach, but Trump himself has yet to publicly appear in front of an audience that is mostly Black.
Despite the disadvantage, Trump made clear that he believes black voters are making the wrong choice.