When Don King, the iconic boxing promoter, dropped the n-word during a rambling, off-color monologue about race in America at a Pastors and Leadership Conference in Cleveland, Ohio, Republican presidential nominee Donald Trump didn't flinch. He remained frozen with a grin plastered on his face.
What could Trump have been thinking at that moment? Perhaps that RNC chairman Reince Priebus was right when he reportedly nixed a planned speech by King at the Republican National Convention this summer — or perhaps that he would be forced to do even more "outreach" to the African-American community to clean up any fallout from the gaffe.
"There's only one Don King," Trump said following King's controversial introduction. "He's a phenomenal person."
The parallels between King and Trump have not been lost on longtime political watchers. Besides their oft-parodied hairstyles, both men have carved out successful careers as what some might call shameless self-promoters. They have also both been repeatedly accused of gaining wealth and fame through the exploitation of others, shady business deals and even ties to organized crime.
And yet, at ages 85 (King) and 70 (Trump), both men have proven to be astonishingly resilient figures in American life. Their outsize personas have become a popular aspect of their brands, even if their hubris can often account for inopportune and incongruous public statements.
For instance, King, one of Trump's few celebrity supporters, has proven to be incredibly hard to pin down politically. He came out aggressively in favor of President George W. Bush in 2004, praising his strength in the face of terrorist attacks and attempts to reach out to the black community. He even went so far as to suggest the president would knock out his Democratic challenger, John Kerry, in a boxing match.
When pressed at the time on his prior support for President Bill Clinton, King told reporters: "I was with Bill Clinton when Bill Clinton was running because I'm a Republicrat. Bill Clinton is a good guy. I love Bill Clinton. I have no problem with Bill Clinton. But Bill Clinton ain't president."
In 2008 and 2012, King switched sides again, coming out in favor of Democratic nominee Barack Obama. Among his patented lines eight years ago was to say that white voters should "ask God to help you pretend that Barack Obama is white," so they would feel less self-conscious about electing the first black president.
Even if his rhetoric was uncouth, he exhibited a penchant for picking winners. Perhaps this is why Trump so eagerly sought his endorsement in 2016, and even hyped it before he actually had it.
"I am the least racist person you have ever met. Believe me, I am the least racist person," Trump told supporters at a June rally in Tampa, Fla. "I get a call yesterday, as an example — street smart guy, smart guy, but very street smart — Don King the boxing promoter. And Don King said, 'Donald, I am endorsing you for president.' You think Don King is going to endorse a racist?"
After initially denying he was backing Trump, citing his 'Republicrat' line, King eventually caved and threw his weight behind the real estate mogul while floating the concept of liberal Democratic socialist Sen. Bernie Sanders joining the GOP standard-bearer's ticket.
"I'm neither Republican nor Democrat. I'm for the American people. And the American people endorsed Trump. And the American people endorsed Bernie Sanders for vice president," King told the website BoxingJunkie.
The endorsement didn't come without its fair share of hand-wringing, even among Republicans. They were uncomfortable with Trump consorting with a man who was convicted of manslaughter in 1966 (he was pardoned decades later) and whose eccentricities (he tends to appear in public adorned with both the U.S. and Israeli flags) threatened to overshadow whatever star power he could lend the campaign.
Trump has struggled mightily to woo black voters amid a steady stream of headlines and statements suggesting that he, and many of his supporters, are prejudiced. King's presence on behalf of his longtime friend appears to be a part of an effort to blunt criticism of Trump's problematic history on matters of race.
But according to David A. Wilson, the founder and executive editor of the African-American news website theGrio, Trump has picked the wrong black surrogate to assuage voters on the issue.
"The only thing Don King has done successfully when it comes to black people is sell them for his own profit. That's as far as his credibility goes, " Wilson told NBC News. "It's sort of a match made in heaven when you look at the two of them."
"The fact that he would drop the n-bomb in his whole speech — in the church — it just goes to show you the seriousness of this campaign," he added.
King tried to diffuse the uproar over his remarks (which came while recounting a conversation he'd once had with the late Michael Jackson) on Wednesday by telling Yahoo Sports that he "slipped" while "speaking in the vernacular we'd use on the street."
It still remains to be seen whether Trump will be the one ultimately taking the fall.