Screenshot from a recent appearance on CNN when former Apprentice contenders Kwame Jackson (left) and Randal Pinkett debated Donald Trump supporter Andy Dean (right)

If there is any way to mathematically stop Donald Trump from having the most delegates at the Republican convention, it pretty much has to happen in New York. If the real estate mogul/reality-TV star/erstwhile Republican manages to get over 50 percent of the vote in every New York district, he’ll score almost 80 of the 95 GOP delegates available. That means only a contested convention will stop him from being the GOP standard-bearer.

With Ted Cruz stumbling over his own words and John Kasich a nonentity, who can step into New York to bring down the Donald? None other than a group of former Apprentice cast mates, who, at great financial and professional risk, are sticking their necks out to warn America that Trump isn’t just erratic and a bigot, and that the very skills that make him a good businessman would make him a terrible president.

“I spoke out consistently since [Trump] announced his candidacy,” said Randal Pinkett, who is now the chairman and CEO of BCT Partners, a consulting firm based in New Jersey. Pinkett has a unique insight into Trump as both an employee and a businessman. He won season 4 of The Apprentice (the first African American to win the show) and worked for Trump directly for years. Nevertheless, that didn’t color his views when his former boss announced he was running for president.

“[I was] denouncing him every time. I’ve done more interviews over the last year than at any other time of my life, except when I won The Apprentice. But people still come to me and say, ‘But where do you stand?’ So clearly my limited megaphone is not loud enough, so that prompted me to reach out to other apprentices,” Pinkett said.

The alumni of The Apprentice, especially the minority-group members, are a pretty close group. They’re connected by the experience on the show, in addition to colleges, mutual business partners and clients. Pinkett first reached out to Kwame Jackson, a season 1 alumnus who is now running Kwame Inc. and consulting PepsiCo on millennial and diversity marketing. Jackson recruited former season 3 cast member Tara Dowdell, who runs a socially conscious public relations and marketing firm in the Greater New York area, and others soon followed. However, it wasn’t easy. Donald Trump is a powerful businessman; he’s threatened former cast mates about speaking ill of him, and in some cases, cast members are still financially tied to Trump’s empire.


“There are a number of other apprentices that declined. I reached out to a number of folks,” said Pinkett. “[I told them] I want to organize a group of us to talk collectively. Are you down or are you not down?”

Eventually, six former cast members (Pinkett, Jackson and Dowdell, plus Marshawn Evans Daniels, Kevin Allen and James Sun)—five African Americans and one Asian American—stood together to denounce Trump’s candidacy for president of the United States. They all describe Trump as having fantastic business skills. Dowdell calls Trump “complex.” Pinkett says that Trump is great at getting people to believe in an idea. But he also has other traits that won’t work so well if he’s trying to run the country, says Jackson.

“Immaturity, petulance, ego and a bombast that are dangerous for the nuclear and terrorism world that we live in,” said Jackson.


“This desire to win at all costs may be great in business,” said Dowdell, “but not in government.”

Much of Trump’s campaign narrative is based on the idea that he is a great businessperson and manager of people. Consequently, the views of those who have worked with him and under him over the years are crucial to understanding what kind of man millions of Americans are voting for.

While television viewers only saw the clips and the final dramatic scenes of Trump saying, “You’re fired,” these men and women worked with Trump for months. Many of them maintained business dealings with him long after the show. If there’s anyone who knows who Trump is, what he’s capable of and how he’s changed, especially on issues like race and gender, it’s this group.  


“The person that I knew then was fair, supported me in my outside projects—he was encouraging—obviously the ego and the bombast was there … but the vitriol, the racism and the sexism and xenophobia—all the things we see now—are total Mr. Hyde. That wasn’t the Dr. Jekyll that I met,” said Jackson, who is clear that if the Trump of 2016 had been running The Apprentice in 2004, he’d have never gone on the show.

“It’s the devaluing of African Americans … that was the turning point for me,” said Dowdell, who, like many of the apprentices, noticed a sharp racial turn in Trump’s politics, especially once Barack Obama was elected president. “When he asked for Obama’s [college] transcripts, he never asked [John] McCain or Mitt Romney or anybody else for those. As a black woman whose qualifications and credentials are always questioned, [I feel] he’s making a space, he’s validating that kind of bigotry at the highest level.”

Pinkett, however, saw some of this coming. Trump’s racial microaggressions almost cost Pinkett the win in the season 4 finale of The Apprentice, and he said he could see Trump’s true attitudes beneath the surface.


“I had seen shades of racism, dating back to the Central Park jogger and my finale on The Apprentice, and discrimination cases and a lack of diversity in the organization. … [But] this is just way beyond anything I could have fathomed from the Donald I worked for and with,” he said.  

Omarosa Manigault, probably the most famous Apprentice cast member, has attacked her fellow alums, accusing them of being bitter ex-employees trying to raise their profiles by attacking Trump. How does this group view Trump surrogates, especially African-American ones like Manigault?

“They’re lost souls,” said Jackson. “Those folks are opportunists. Now, everyone is an opportunist to some degree, but at what cost? Your self-worth? Your community? Your value? To help a man who is not in favor of our community—to say the least—get elected? I don’t understand.”


If they’re lucky and their collective voices are finally loud enough, maybe some of those lost souls will change their minds about Trump by the time they go to the polls. 

Jason Johnson, political editor at The Root, is a professor of political science at Morgan State’s School of Global Journalism and Communication and is a frequent guest on MSNBC, CNN, Al-Jazeera International, Fox Business News and SiriusXM Satellite Radio. Follow him on Twitter.