Donald Trump's Behavior Will Lead to More Trials: Apprentice Winner

Former President Donald Trump is not likely to change his business methods, even after facing a major legal blow in New York last week, said a former star of The Apprentice and ex-employee at The Trump Organization.

Trump, his former colleagues and his two eldest sons were hit with $364 million in fines on Friday and barred from conducting business in New York for several years after Judge Arthur Engoron ruled against the former president in the business fraud suit brought by New York Attorney General Letitia James. Trump has repeatedly dismissed the suit as “corrupt” and is expected to appeal the ruling.

According to Randal Pinkett, who won the hit reality show The Apprentice in 2004, Engoron’s ruling is likely not the last of fraud cases that Trump will be handed. Pinkett, the first Black person to win the show, told the Daily Express US that he expects “to see more cases” because he doesn’t “expect Donald to change his behavior.”

Randal Pinkett (left) and former President Donald Trump search for the next “Apprentice” candidates at Trump Tower in New York City. Pinkett said this week that he doesn’t expect the recent ruling against Trump’s business…

Bennett Raglin/WireImage

“Look at how difficult it was for him to keep his mouth shut with E. Jean Carroll. He couldn’t do it,” said Pinkett, who spent a year-long apprenticeship at The Trump Organization after winning Trump’s reality show. “It lasted a couple of days and then he was back in court. I hope he says something again because she will bring him right back into court.”

The former president was ordered to pay Carroll $83.3 million last month for defaming her in 2019 after she first publicly accused him of raping her in a New York department store in the 1990s. A separate jury found Trump liable for sexual assault and defamation in May 2023, and awarded Carroll $5 million. Despite both rulings, Trump has Trump has still made attacks against the former magazine columnist.

“My point is that there will be more cases because it is very difficult for Donald to change his behavior because he has lived with this privilege all his life,” Pinkett told Daily Express. “He believes he can do and say what he wants. But he cannot. The cases will come, he will continue to have these tussles in the courtroom as long as he stays true to who he is.”

Newsweek reached out to Trump’s campaign via email for comment.

Pinkett has been critical of the former president, including raising concerns during the 2016 campaign prior to Trump’s term in office. In 2018, Pinkett told MSNBC’s Joy Reid that there was “no question in my mind” that Trump is “a racist.”

Trump has faced backlash from several other The Apprentice stars, including Season 5 winner Summer Zervos, who sued him in January 2017 for defamation after Trump called allegations that he sexually assaulted her “outright lies.” Zervos dropped the suit in 2021 without reaching a settlement.

Pro wrestling star Bill Goldberg said he had a “miserable” experience while as a contestant on the show, calling Trump “a piece of work” and claiming that the former president “didn’t have any social skills.”