Donald Trump Apprentice Winners: Where Are They Now?

Donald Trump’s reality TV show, The Apprentice, dominated ratings during its original run from 2004 to 2017. The business-themed competition offered contestants the chance to showcase their skills and ambition, vying for the opportunity to work for Trump himself. As the show gained immense popularity, winners became household names overnight, with fans eager to know what happened to them after the cameras stopped rolling. In this blog post, we dive into the lives and careers of the Donald Trump Apprentice winners and explore where they are now.

Bill Rancic (Season 1 Winner)

Bill Rancic emerged victorious as the winner of the inaugural season of The Apprentice in 2004. As part of his prize, he worked on the Trump Tower Chicago project. Following his win, Rancic went on to become a successful entrepreneur, author, and television personality.

Rancic married his fellow reality TV star, Giuliana Rancic, and the couple has since become powerhouses in the entertainment industry. Bill Rancic has founded multiple ventures, including a motivational speaking business and a real estate company. He has also appeared in various television shows, providing business advice and insights.

Kelly Perdew (Season 2 Winner)

Kelly Perdew triumphed as the winner of The Apprentice Season 2, earning a one-year contract to work for Trump Entertainment Resorts. After his time on the show, Perdew continued to pursue a successful career.

Perdew co-founded the consulting firm TargetClose and later became the CEO of Fastpoint Games. He has also provided expert commentary on business-related topics on various news networks. Furthermore, he has volunteered his time to support charitable organizations and has shared his knowledge through public speaking engagements.

Kendra Todd (Season 3 Winner)

Kendra Todd became the first female winner of The Apprentice in Season 3. Her prize included overseeing the construction of the Trump Tower Tampa. Following her victory, Todd made significant strides in the real estate industry.

Todd founded her own real estate company, The Kendra Todd Group, which specializes in luxury properties. She has expanded her reach by authoring books on real estate investing and serving as a contributor for major news outlets. Furthermore, Todd has taken on speaking engagements to share her expertise and empower others.

Randal Pinkett (Season 4 Winner)

Randal Pinkett, an accomplished entrepreneur and Rhodes Scholar, won Season 4 of The Apprentice. Pinkett received the opportunity to launch his own project with Trump. Since then, he has continued to excel in various business endeavors.

Pinkett founded the consulting firm BCT Partners and has become a sought-after public speaker. He has held executive positions in multiple organizations, including serving as chairman of the business advisory boards for both Rutgers University and Clemson University. Pinkett has also authored books on leadership and business strategy.

Sean Yazbeck (Season 5 Winner)

Sean Yazbeck triumphed in Season 5 of The Apprentice and was tasked with overseeing the Trump SoHo Hotel-Condominium project. After the show, Yazbeck continued his successful career in the hospitality industry.

Yazbeck has held executive positions with various hotel groups and has embarked on entrepreneurial ventures, such as founding the luxury travel club MyVIP. Moreover, he has been involved in philanthropic efforts, supporting charitable organizations focused on education and healthcare.

Stefanie Schaeffer (Season 6 Winner)

Season 6 of The Apprentice introduced Stefanie Schaeffer as the winner. Schaeffer, an attorney and entrepreneur, won the opportunity to work on the Trump International Hotel and Tower project in Chicago.

Since her win, Schaeffer has remained actively involved in legal practice and has founded her own marketing company, Schaeffer Marketing Group. Additionally, she is a public speaker and has shared her insights on business and leadership at renowned events.

Brandy Kuentzel (Season 7 Winner)

Brandy Kuentzel emerged victorious in Season 7 of The Apprentice and worked on the Trump International Hotel & Tower Las Vegas project. Post-show, Kuentzel has made notable strides in the business world.

Kuentzel has served as a regional director for a healthcare management company and has held executive roles in the healthcare industry, specializing in strategic planning and business development. She has also devoted time to community service and has been actively involved in charitable initiatives.

Annie Duke (Celebrity Apprentice, Season 2 Winner)

While not a part of the regular Apprentice seasons, Annie Duke claimed victory in the second season of Celebrity Apprentice. As a professional poker player, Duke showcased her strategic thinking and decision-making skills.

After her win, Duke continued her poker career and expanded her expertise into professional speaking engagements, focusing on decision-making and negotiation strategies. She has contributed to books related to poker and has utilized her platform to advocate for social causes.


The winners of The Apprentice have demonstrated their ability to capitalize on their successes, each forging their own paths in various industries. From real estate moguls to marketing experts and philanthropists, these individuals have utilized their experience on the show to propel their careers forward.

While some winners have remained closely aligned with the business world, others have branched out into entertainment, hospitality, and even professional poker. Regardless of their chosen paths, the influence of The Apprentice continues to resonate in the endeavors of its talented winners, paving the way for future business leaders.

For more about the careers of The Apprentice winners, you can refer to their official websites or explore their accomplishments in greater detail through their books, speaking engagements, and media appearances.

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