In 2011, shortly after Donald Trump first publicly latched onto the theory that President Obama wasn’t born in the United States, Randal Pinkett knew he had to do something.
The winner of Season 4 of The Apprentice wasn’t interested in embarrassing Trump, but he was interested in reaching out to him as a former colleague, as somebody who he thought had Trump’s respect. Pinkett, the only black winner in the seven seasons of the show, called his old boss.
“I said, ‘Donald, if you really want to be president, this is not the way to go about it,’” Dr. Pinkett told The Daily Beast. “Because you are offending people of color. Including me. Including me, Donald!”
The Donald, said Pinkett, wasn’t buying it. “He basically blew me off completely,” said Pinkett. “He asked me if I was trying to make this a publicity issue even though I called him privately.”
The phone call ended coldly and abruptly, and Pinkett didn’t hear from his former boss again for a year.
In the days following the release of video of Trump bragging about sexual assault, rumors have swirled that a similarly incriminating tape exists of the Republican presidential nominee using the n-word. The search for the tape has gotten so intense that Apprentice producer Mark Burnett has released statements clarifying that while he is not a Trump supporter, he cannot release footage from The Apprentice without breaching a spider web of contracts. Whatever footage of alleged depraved behavior exists, the public won’t likely see it for quite some time. If ever.
Pinkett doesn’t recall his former boss engaging in racism that overt and aggressive, but he does have a lingering bad taste in his mouth over how he was treated at the end of his season of the show. In an Us Weekly interview with Trump that ran a week before the finale aired in September 2005 (the same month Trump was recorded bragging about grabbing women “by the pussy,” natch), Trump was asked to describe Pinkett and fellow finalist Rebecca Jarvis.
“He described me as ‘lazy,’” Pinkett said. “He described my white female fellow finalist as ‘beautiful.’”
Their task in the finale was to raise money for charity. Pinkett raised $11,000 for his chosen charity, Autism Speaks. Jarvis did not raise any money for her chosen charity, and Pinkett was crowned the winner.
But after he was “hired” by Trump, producers called Pinkett back into the boardroom, where Trump asked him, on live television, if Pinkett would be willing to share the title of The Apprentice with his fellow finalist. Pinkett said no.
“She was much younger, much more junior, much less experienced,” said Pinkett. He thinks Trump asked him to share his title because he wanted to hire a pretty white woman.
Pinkett said his experience working for the Trump Organization for a year after the show’s finale was mainly positive. But during his apprenticeship, he noticed that he was the only person of color at the executive level. And as a result, he was put in an awkward position.
At the time, the Trump Organization was competing for a coveted casino license in Philadelphia. Pinkett, a Philly native, said he was routinely asked to represent the organization at meetings and community events designed to sway people in the neighborhood to come around to the idea of letting Trump put one of his projects in their backyard. Without the community’s approval, the gambling commission wouldn’t grant a casino license.
“The forums got contentious and ugly, kind of like the campaign trail,” recalled Pinkett. “The executives from Trump would come in and try to begin talking about what they’d do for the community. And at every forum I went to, they never got through their presentation because the vocal community members shut them down and they had to be escorted out.”
Toward the end of his apprenticeship, Pinkett told Trump Organization executives that he didn’t want to attend another community-courting event. He said they didn’t take his refusal very well. His business consulting firm BCT Partners did business with the Trump Organization, and when Pinkett balked at serving once again as the face of Trump’s Philadelphia ambitions, Trump executives told him they’d pull their contract with BCT Partners.
Pinkett has spent the intervening years running his own business, giving speeches, and writing books. In one of them, Black Faces, White Places: 10 Game-Changing Strategies to Achieve Success and Find Greatness, he details his experience in the finale of The Apprentice when he, despite outperforming his competition, was asked to share the title with a white competitor. He’s been speaking about how he was treated by Trump and the Trump Organization for years, including a recent ad that he shot for MoveOn.
But what of The Donald, who declared himself a changed person since the recording of the now-infamous tape in 2005? “Donald surrounds himself with people who don’t challenge him,” said Pinkett. “He weeds out people who want to challenge Donald or who want to be critical of Donald.
“I don’t think he’s learned anything.”