But the head of the Black Republican Caucus of Florida says Trump's state campaign doesn't seem to care much about Jackson's efforts to convert more African-Americans to the cause. In fact, he says Karen Giorno, Trump's Florida campaign manager, has disregarded his advice and all but frozen him out of Trump's efforts to win the Sunshine State.
"Mr. Trump really does have a sincere, passionate interest in black outreach, but his campaign staff has dropped the ball," Jackson tells New Times. "That all starts with Karen Giorno. She has repeatedly failed at embracing blacks across the state."
Giorno didn't respond to an email and phone message from New Times.
Jackson's critiques come after news broke that Giorno refused to let Jackson stay backstage at a recent Florida rally and then, according to Jackson, told him flat-out that Trump didn't need black votes.
"The crazy part about it is that the Secret Service had already cleared me to be back there, and yet she made a scene and claimed that she didn't know who I was," Jackson says.
But Jackson says the problems with minority outreach inside Trump's Florida operation go much deeper than just one misstep by Giorno at a rally.
The West Palm Beach native says he had hoped to use his position to help Trump avoid Mitt Romney's missteps in 2012; Jackson thinks Romney started much too late in reaching out to black voters. Jackson says that he believes African-Americans are ready to leave the Democratic Party but that they need a sustained outreach effort.
"I have been saying repeatedly that you cannot go into a black community in the ninth hour of a campaign and ask them to vote for a GOP candidate," Jackson says. "The party has done a piss-poor job of courting the black vote over 50 years. So you have to have more vested interest in time and in your financial effort for the whole campaign, not just in the last 100 days."
That's why Jackson volunteered early this year to help Trump with black outreach. The real-estate magnate and his national staff have been enthusiastic about Jackson's work, the caucus head says. The state campaign — not so much.
"I have called and emailed and text-messaged every way I can to Karen and her staff... trying to impress on her how important this outreach is. It's fallen on deaf ears," Jackson says. "This is why you have this scenario playing out where the narrative is that Trump couldn't give two craps about blacks, which is just not true."
Polling certainly doesn't show Trump making inroads with black voters; one national poll in July showed just 6 percent of black voters leaning toward the GOP candidate. In battleground states Ohio and Pennsylvania, that poll found literally zero percent of black support for Trump.
Jackson says he's still a true believer and will continue working to get Trump elected in November. He says he believes Trump will rebuild the military and change the economy for the better, even if Jackson is frustrated with Trump's campaign operation in his home state.
"My physical attitude now is that I've hit this crossroads, but my spirit will not allow me to stop working for Mr. Trump," Jackson says. "I know this is much bigger than me. It's much bigger than any one person."