Over the years, Mr. Trump has deflected criticism by citing friendships with black celebrities. In the 1980s, he became a fixture ringside in Atlantic City, befriending the boxing legends Muhammad Ali and Mike Tyson and the promoter Don King. He briefly owned a United States Football League team, leading to friendship with its star player, Herschel Walker.
As the hip-hop industry flourished in the 1990s and 2000s, rappers often used Mr. Trump’s name in lyrics as a symbol of wealth and flash. Along the way, he became friendly with Sean Combs, Snoop Dogg and Russell Simmons.
Mr. Trump boasted about the mention of his name in rap videos, asking one of the secretaries to find examples on YouTube and play them for guests. “The blacks love me,” he said proudly.
By 2015, now running for president, he stopped using “the” before describing ethnic groups. While some black celebrities stood by Mr. Trump, other relationships have soured because of his politics. Mr. Simmons, in an open letter that year, told his estranged friend to “stop fueling fires of hate.”
‘This Is Just Politics’
The foundation of Mr. Trump’s campaign was built on questioning the birth of the first African-American president. To Ms. Manigault Newman, a conversation she had with Mr. Trump about the “birther” campaign during a break in taping of “The Apprentice,” was the first time she saw him as overtly racial.
“He was bragging about it,” she said in an interview. “I asked him, ‘Why would you do this?’ He said, ‘This is just politics. This is what happens in politics, you do opposition research.’”
And yet like others in Mr. Trump’s orbit, Ms. Manigualt Newman did not find it so objectionable that she broke with him at the time. She spoke out about what she considered Mr. Trump’s racism only after she followed him to the White House and was subsequently fired.