Details About Bill Rancic And Donald Trump's Relationship Revealed

Way back in the early 2000s, television producer Mark Burnett was riding high with the success of "Survivor," the CBS hit that blew the doors open for the hundreds of reality TV shows that followed. In 2004, Burnett unveiled a new NBC reality competition that shared some similarities with "Survivor," but was set in the concrete jungle of Manhattan as opposed to the actual jungle inhabited by "Survivor" contestants. 

That show was "The Apprentice," centered around bombastic New York real estate developer Donald Trump. The assembled contestants, all aspiring entrepreneurs, were tasked with undertaking an array of business-themed challenges, keeping one key goal in mind: to impress Trump and his advisers. Rather than have their torches snuffed after "the tribe has spoken," "Apprentice" wannabes were called into a boardroom and eliminated by Trump himself, uttering two words that became the show's catchphrase: "You're fired."

That debut season of "The Apprentice" was a hit, and when the dust settled it was Bill Rancic who was declared the series' first winner. His association with the show wound up laying the foundation for his own future success, which arguably wouldn't have taken place without "The Apprentice." Two decades later, Rancic is a successful entrepreneur and media personality, while Trump became the controversial 45th president of the U.S. As the ex-POTUS takes another shot at the White House — in between courtroom appearances, that is — read on to reveal details about Bill Rancic and Donald Trump's relationship.

Entrepreneurship was hard-wired into Bill Rancic. Prior to competing on Season 1 of "The Apprentice," he began selling cars at age 15. While attending Loyola University, he started his own business, washing and waxing boats, ultimately graduating cum laude. 

Pitted against all those other entrepreneurs, Rancic distinguished himself; finally, it came down to him and Kwame Jackson, a Wall Street exec with a Harvard MBA. When Donald Trump made his final choice, it was Rancic, not Jackson, who emerged victorious. "The American Dream is still alive out there, and hard work will get you there," Rancic said during a news conference after the finale, as reported by CBS News. "You don't necessarily need to have an Ivy League education or to have millions of dollars startup money. It can be done with an idea, hard work and determination."

Interviewed by SFGate, Rancic revealed that in his quest to win those weekly challenges and impress Trump, he'd pushed himself to the limit on multiple fronts. "It was like a marathon," he explained. "Just week after week of operating on no sleep, so you're mentally and physically beat up, you know? I lost 16 pounds during the taping of it and I wasn't trying to lose weight. You're out there giving it your all." As he was about to find out, however, winning was just the first step; the real work still lay ahead.

When Donald Trump chose Bill Rancic over Kwame Jackson as the first winner of "The Apprentice," was there more than just their business acumen behind the decision? That's the allegation made by Michael Cohen, Trump's former lawyer, and now a diehard detractor of the ex-president. In his book, "Disloyal," Cohen recalled the dilemma facing Trump, from Trump's perspective: should he pick a gay Black man, or a straight white guy?

According to Cohen, Trump balked at making Jackson his first TV apprentice. "There was no way I was going to let this Black f** win," Cohen recalled Trump saying (via the Daily Mail), alleging Trump referred to Jackson using a homophobic slur. Trump viewing the competition in racial terms was something that was corroborated by "The Apprentice" co-producer Bill Pruitt. Interviewed for the book "The Method to the Madness: Donald Trump's Ascent as Told by Those Who Were Hired, Fired, Inspired — and Inaugurated," Pruitt recalled Trump huddling with producers and advisers — including on-air adviser Caroline Kepcher, who shared her belief that Jackson was more deserving of the win. As reported by Newsweek, Pruitt alleged Trump used the N-word when explaining why he didn't see Jackson as the victor of the season.

Interviewed by Salon in 2016, Jackson was asked if he thought race was a factor in Trump choosing Rancic over him. "At the time, no; now, yes," he said. 

While "Survivor" winners receive a cool million, Bill Rancic walked away from the first season of "The Apprentice" with a job — albeit one that paid him a $250,000-a-year salary, as the president of a Trump company. In that capacity, Rancic was tasked with overseeing the construction of a new Trump hotel/condo development in Chicago, on the site of the Chicago Sun-Times building. Still, Donald Trump left no doubt as to who was actually in charge. "Don't worry, you're going to have plenty of supervision of that building, I don't care if you're president or not," Trump told Rancic, reported CBS News. "I'll be the one supervising."

Working for the Trump Organization promised to be an eye-opening experience for Rancic; remember, prior to "The Apprentice," he'd operated an online cigar business (which was apparently not as successful as the show had hyped it up to be). "I'm a small-time entrepreneur, and I've gotten to see what the big-time is like," Rancic told Bloomberg, insisting that his gig with Trump was the real deal, not just reality-show smoke and mirrors.

While eyebrows might raise in light of the Trump's fraud trial and the massive penalty he received, back in 2005 Rancic praised him for being a straight shooter in the business world. "I like how he does business," Rancic added. "He's above board. He takes the high road. I wouldn't be here if he didn't."

There's been much discussion about how much reality actually occurs within so-called reality shows, and it would be easy to assume that the job offered as the grand prize in a TV competition may not be completely legit. Such was the case when Bill Rancic was placed in charge of overseeing the $700 million Trump International Hotel & Tower. As Chicago financier Bruce R. Cohen told The Ledger, putting a guy whose prior experience was selling cigars in charge of such a massive project seemed somewhat ill-advised, comparing managing something so complex to conducting a symphony. "I don't know how somebody can conduct the Chicago Symphony Orchestra if they've never gone to a concert before, and if they've never played any of the instruments," Cohen mused.

Trump, however, insisted that Rancic's duties would be both significant and authentic. "It will be an important job," Trump insisted. "He will be a project manager." While Trump also contended that Rancic would be surrounded by seasoned pros entrusted to show him the ropes, he also hinted that Rancic's real role was more of a promotional one, given how much the building's exposure on "The Apprentice" was intended to spur sales of condos. "I felt that this was a great opportunity to promote a great project," Trump said. 

For his part, Rancic conceded there was a lot to learn. "I think I'm going to need some guidance," he said.

When examining the relationship that developed between Donald Trump and Bill Rancic, it speaks volumes that Trump was only contractually obligated to keep the "Apprentice" winner on the payroll for one year — but kept him on for another. "He's so talented that I thought he might want to go out on his own and make millions," Trump said in a statement, as reported by Digital Spy. "We're lucky to have him back for another year and I can rest assured that my Chicago project is in the best of hands." 

Rancic also chimed in with a statement, offering his gratitude to Trump and expressing his excitement about sticking with the project. "It will be a privilege to spend another year with him," Rancic said. Meanwhile, Digital Spy also reported that Rancic would also be returning to "The Apprentice," filling in whenever Trump's advisers, George Ross and Carolyn Kepcher, were unable to be on the show due to business matters. 

Later that year, Rancic announced that when his contract ended in March 2006, he'd be moving on. "I'm gonna go out and start another business of my own," he said during a global leadership forum held in Malaysia, reported Today. Ultimately, Rancic changed his mind and decided to stay put for a third year, working in sales and marketing for the project. 

In 2015, Donald Trump transformed his life forever when he descended on a gilded escalator in Trump Tower to announce his candidacy for president of the United States, an office to which he was ultimately elected. 

In 2016, ahead of the election, Rancic shared his opinion about what he expected a potential Trump presidency to look like. "I think he'd be a great president, certainly," Rancic told CBS News. "I got to watch him from the inside and I was able to see how he works and how he does deals and how he was able to negotiate in difficult times." After Trump was elected, but prior to taking office, Rancic praised the president-elect's work ethic while interviewed by CNBC. "He's a hard worker," Rancic said. "You saw him on that campaign trail. He was doing six, seven, eight, 10 stops a day."

In 2017, Bill Rancic was delivering a speech to the Schaumburg Business Association when he was asked to share his opinion of how Trump would fare as president. "He knows how to lead. He knows how to get things done," Rancic said, reported the Daily Herald. "If he can do for our country what he did for me, I think America is going to be in a really good place," he said. Of course, he pointed out, the real test of Trump's presidency would come when he ran for a second term.

After three years working with the Trump Organization, Bill Rancic finally made an exit. His next project brought him back to the realm of television, hired to host online series "In the Loop with iVillage," and then hosting his own A&E series, "We Mean Business." In 2009, Bill and his wife, Giuliana Rancic, began appearing in their own reality show, "Giuliana and Bill," which ran until 2014.

Back in 2006, Bill told People of his desire to eventually team up with Donald Trump in some type of business venture. "One day I'd like to be partners on a project with Donald Trump," he said. "I think it would be a great ending to the story."

While that never happened — and, given the current circumstances, seems highly unlikely — Bill nevertheless had nothing but good things to say about his former boss after he'd taken up residence in 1600 Pennsylvania Avenue. During a 2018 interview with Us Weekly, Bill continued to heap praise on then-President Trump. "He was great to me. He treated me very fairly. He genuinely wanted to lift me up," Bill said of his one-time boss. "He wanted me to do good things [and] arm me with the tools to succeed in life. It's an opportunity that I'm always grateful for and that I will always appreciate."

In 2005, Bill Rancic first met Giuliana DiPandi, then working for E! News. The electricity between them was apparent during their ultra-flirty interview, particularly when she asked him about his love life — and he threw the question back to ask about hers. The two became an item not long after, and were married in 2007.

When the Rancics were interviewed by CBS News in 2016, after nearly a decade of marriage, he gave all the credit for meeting his wife to his one-time boss, Donald Trump. "He was incredible to me and changed my life," Bill said. "I give him a lot of the credit. If it wasn't for him, I wouldn't have met my wife and things would have been different for me."

Giuliana Rancic (née DiPandi) echoed those sentiments in a solo interview with CBS News later that same year. "We always say if it wasn't for Trump, we wouldn't be together," she declared. "I met my husband because he won 'Celebrity Apprentice.' He was doing charity work for Boys and Girls Club and we met and were engaged eight months later." She also indicated why it was unlikely that her husband would ever say anything negative about Trump, due to his unwavering loyalty. "He never turns his back on people who have been his friends or who have helped him out," she added. 

For Bill Rancic, becoming the first winner of "The Apprentice" was indeed life-changing. Not only did he gain a high-paying job working under Donald Trump, he also became a media personality in his own right, managing the not-always easy trick of maintaining fame after encountering it via reality television. That ability was also something that Rancic credited to Trump, praising his abilities to garner attention for himself. "He knows how to brand," Rancic explained in an interview with CNBC. "He knows obviously how to use the media and he does it very effectively. There's no question about it."

Speaking with Business Insider, Rancic also recalled one of the best pieces of advice that Trump had ever given him, one that continued to resonate with him in his subsequent business dealings. "You know, the one thing I learned from Donald Trump is that if you want to be successful, you have to be a conductor," Rancic said, explaining how an orchestra conductor will assemble a great collection of musicians who have mastered their instruments. "The conductor himself may not be able to play each and every one of those instruments," Rancic added, "but boy, when he gets them all together, they make beautiful music." The point he was making: surround yourself with the best people you can find, steer them in the right direction, then let them do what they do so they can work their magic.

Long before "The Apprentice" made its television debut, Donald Trump unveiled his first book, 1987's "The Art of the Deal," which became a bestseller that led to many more books.

Bill Rancic certainly took a page from Trump in the publishing department, and went on to write a few books of his own. The first of these was "You're Hired: How to Succeed in Business and Life." Trump wrote the forward. That book, along with his fame from "The Apprentice," opened the door to a successful career as a motivational speaker, with Bill commanding a fee ranging from $30,000 to $50,000 per speech.

Bill went on to write another business-themed book, "Beyond the Lemonade Stand: Starting Small to Make it Big," and then offered marital advice (a topic the thrice-married Trump wisely chose to avoid in his books) in "I Do: Now What?" — co-written with his wife, Giuliana Rancic. In 2018, Bill published his first novel, "First Light." Speaking with the Chicago Tribune, Bill admitted he recognized why his debut as a novelist might be met with skepticism. "I think I felt more pressure because I knew going in that people didn't expect this from me, and I was well-aware that some may be more critical in their critique," he said. "And this being my first novel, I felt some pressure to get it right — so that it wouldn't be my last one."