Details About Bill Rancic's Relationship With Ivanka Trump

Since winning the first season of "The Apprentice" in 2004, Bill Rancic's career has soared higher than the show's ratings. Formerly an online cigar entrepreneur, Rancic enjoyed a year on the staff of the Trump Organization as the reality show's champ before pursuing his own interests again. He and his wife, former E! News reporter Giuliana Rancic, have written bestselling books, hosted several cable shows, and co-own a series of restaurants. Rancic also helped his wife launch her own prosecco brand, and he has his own podcast, "Dollar Bill.". 

Rancic was invited back on a number of occasions to serve as a "boardroom advisor" on the hit NBC show. As such, he observed the teams fulfilling their assigned tasks and offered their opinions to the star, Donald Trump. Joining him in the boardroom in 2006 was Ivanka Trump. Just 24 years old at the time, Ivanka had already been named vice president of real estate development at her father's firm. The following year, the billionaire's older daughter would go on to launch her jewelry line and proceed to venture into fashion. Sharing an entrepreneurial spirit and a Trump connection, Ivanka and Rancic became friends. They may not be the closest of buds — they live in different cities and work in different fields — but they'll always be bonded by the time they spent helping the mogul decide which contestant should hear the immortal words "You're fired!"

Bill Rancic and Ivanka Trump were co-workers for a brief time when he won his apprenticeship at The Trump Organization. He opted not to extend his one-year contract, preferring to return to entrepreneurial life. Rancic also guested on "The Apprentice" several times as one of the mentors who helped judge teams' performances during their assigned tasks. Some of those appearances allowed him to work with Ivanka again. In a 2006 interview with People, Rancic was asked his opinion of the Trump daughter. "Ivanka is really cool," he summed up. "I was really impressed with how sharp she is. She's very down-to-earth and an overall very nice person." Rancic added his opinion that Ivanka and her father "have a great relationship," and that Trump was guiding her in her business pursuits. 

Apart from a promotion they did in 2010 for HP's "Big Payback" initiative, Rancic and Ivanka don't appear to be close friends. Still, their luxe lives and their values are similar, and they both seem determined to steer clear of politics. Other than his 2016 opinion (per CBS News) that Donald Trump would "be a great president," Rancic hasn't shown any public sign of being a MAGA loyalist. As for Ivanka, she distanced herself from her dad after he left the White House in 2020.

Ivanka Trump seems to support her pal's business ventures. Back in 2017, when Trump was still in her capacity as a senior advisor to her father during his administration. She and her husband, Jared Kushner, treated themselves to a night out at Washington, D.C.'s RPM Italian, one of a series of restaurants Rancic and Giuliana co-own with business partners. It happened to be the city's Restaurant Week, in which diners at selected restaurants can enjoy a full three-course meal for just $35. That's about what you'd spend on RPM's chicken parmesan or lobster ravioli alone. (Don't ask about the porterhouse steak unless you have deep pockets.)

According to a report quoted by the Daily Mail, a witness at the restaurant saw the couple's server put their bill on the table after the meal, but another staffer immediately rushed in to insist the dinner was on the house. Kushner refused the generous offer, explaining government employees aren't allowed to accept gifts valued at more than $20. He went on to pay the check. The gesture made for good optics, but it turns out this might not have been necessary. The Mail cited the U.S. federal code of conduct for employees, which states executive branch workers may accept larger gifts if they come from established friends. While Rancic doesn't seem to have been personally present that day, Trump and Kushner could still likely have taken the restaurant up on the offer thanks to this loophole.