His troubles began when he attended a rally by then-presidential candidate Donald Trump in Redding, California, in June 2016. Cheadle was a California congressional candidate at the time, and he stood out as a Black Republican.
Cheadle laughed along with everyone else, but that soon changed. He left the rally early, took a nap at a friend’s house, and by the time he woke up, he had gone viral.
His phone was filled with texts and voicemails from reporters wanting interviews. There also were angry messages from family and friends wanting to know why he let Trump insult him. His Facebook page was filled with both Black and White people calling him “Uncle Tom” and the N-word and threatening to kick his butt.
“Oh, you got to be kidding,” he thought at the time. “America doesn’t have anything better to do than this?”
Cheadle was about to discover the loneliest place in the universe may be reserved for a man who becomes known as Trump’s Black buddy.
“Man, I did it for a joke,” he says now. “When I did it, people around me burst out laughing.” He sighs before adding: “Then the joke turned sour.”
How Cheadle’s life changed
What’s happened to Cheadle since that day in 2016, though, shows how tough the Trump campaign’s challenge is going to be. For starters, he is no longer Trump’s “African-American friend.”
“I was dating a woman and we broke up because of that,” he says. “The whole thing was kind of stupid. She was an influential Democrat and she just couldn’t handle the pressure of even being seen in public with someone associated with Trump.”
Cheadle says he has since lost respect for some Black Republican conservatives. He compares them to ventriloquists’ dolls — puppets employed by powerful white people to mouth political platitudes that hurt Black people.
He also says he was deflated by how the Republican party reacted to the death of Herman Cain, a former Republican presidential candidate. Cain, who was Black, died after contracting coronavirus soon after attending a Trump rally without wearing a mask.
“It was sad that he died, but even more sad that he was not given any honor by the Republican Party,” Cheadle says. “It was like, ‘He’s dead. No problem. Goodbye.'”
“I would be surprised if he did as well (with Black voters) as he did last time,” he says.
“Even when Obama was on the ticket, he got like 95% of the Black vote,” says Perry, chairman of the political science department at Howard University in Washington. He says some Black Republicans have long put more emphasis on conservative principles than skin color. They like Trump’s record of appointing conservative federal judges, for example.
“I don’t think there’s much they can do (to sway voters),” Perry says of Trump’s Black campaign surrogates. “All they can do between now and November is ignore the racial elements of the Trump administration.”
Why he soured on Trump
Cheadle won’t play along with that strategy. The divorced father of three is a gregarious man whose voice rises when he starts talking about Trump’s treatment of Blacks. He grew up in inner-city Oakland and Cleveland and still remembers seeing race riots erupt during the mid-1960s.
He is not an unusual character in the Black community. Virtually every major Black leader — Frederick Douglass, Booker T. Washington, Malcolm X and even Obama — has blended conservative principles like self-help and economic empowerment with progressive ideas.
But Cheadle remains skeptical about the Democratic Party. He doesn’t like Obamacare and didn’t vote for Obama because he says Obama was an “elitist” who never did much for Black people. He doesn’t think Joe Biden, the Democratic presidential nominee, has done much for Black people, either.
And Cheadle still reveres the Republican Party, or at least the 19th-century version of it, which was willing to go to war to end slavery.
“They freed the slaves,” he says of the party of Lincoln. “They literally gave their lives for the cause.”
That’s part of the history Cheadle carried with him when he went to hear Trump speak in 2016. He thought the media portrayals of Trump were too harsh, and he wanted to have an open mind.
Many thought that Trump’s comment that day — “my African-American” — was condescending. Cheadle didn’t think so at the time.
“We’re so polarized and sensitive in this country now. It’s frightening,” he said a day after the rally.
“I pretty much went into hiding,” Cheadle says. “I didn’t want to really be in public because it was too ugly. This is gun country up here. People don’t play.”
But he refuses to call Trump a racist because the term is so loaded. Instead he says Trump has a “white superiority complex.”
“When you say someone is racist, it’s damning but it’s not productive,” he says.
How he’s voting in 2020
The George Floyd racial protests and the resurgence of Black Lives Matter also hit Cheadle deeply. He says the Floyd video made “me sick to my stomach.”
And his politics have evolved so much in recent years that he no longer calls himself a conservative.
“A conservative means you’re in favor of the status quo, and the status quo is keeping the white superiority complex in power,” he says. “I’m not for that. I am an independent, an independent thinking person.”
But he hasn’t made another big decision — who he’s going to vote for in November. He calls himself undecided between Biden and Trump.
“You’re asking me to choose between projectile vomit and diarrhea,” he says.
Cheadle does like Biden’s vice-presidential pick, Kamala Harris. She would be the first vice-president who is Black and South Asian. He believes Harris’ race could make her more empathetic toward Black people.
“If I vote for Biden, it’ll probably be because I’m voting for Harris,” he says.
And Cheadle hasn’t given up on politics. He plans on running for office again.
Does he ever worry that he’ll forever be known as Trump’s “African-American?” Just last month, a news crew from India contacted him seeking an interview about his famous exchange with Trump.
“It doesn’t worry me,” he says. “In the overall scheme of things, I’m happy that it happened. It’s given me a platform to use to better my people. All of that headache and the names I’ve been called is a small price to pay.”
Trump has since found new Black allies, including former NFL running back Herschel Walker, who recently said “it hurt my soul” to hear people call Trump a racist.
We’ll find out in November if these Black supporters make any difference.
In the meantime, Cheadle has finally got enough distance from that Trump rally in 2016 to start working on his memoir. He already has a title.
It’s called, “My African-American.”