Melania Trump’s closest and most enduring friend is Stephanie Winston Wolkoff. While she is not a household name like a singer or actress, Stephanie played a pivotal role in Melania’s life—both personally and professionally—and their relationship has fascinated the public due to its dramatic evolution.
Stephanie Winston Wolkoff is a former fashion and event planner with deep roots in the New York social and fashion scenes. Before her connection to the Trumps gained attention, she made her mark as the founding fashion director for Lincoln Center and as a long-time organizer of the Met Gala while working with Vogue and Anna Wintour. She was a respected figure in elite circles, known for her sharp organizational skills and discretion—qualities that initially made her an ideal confidante for Melania Trump.
Their friendship began in the mid-2000s and blossomed over shared interests in fashion, parenting, and life in the New York elite. By the time Donald Trump launched his presidential campaign, Stephanie had already become Melania’s most trusted advisor and helper. She helped plan high-profile events and guided Melania through the complex maze of Washington politics and social expectations. When Donald Trump won the presidency, Stephanie took on an official role as senior advisor to the First Lady, helping to coordinate her inauguration and public appearances.
What makes this relationship particularly intriguing is how it unraveled. Despite their close bond, things took a sharp turn after Stephanie was blamed for financial controversies related to the Trump inauguration. She eventually left her position, but the real shock came later: Stephanie wrote a tell-all book titled Melania and Me, revealing details about their friendship, Melania’s private views, and life inside the Trump White House.
Stephanie secretly recorded conversations with Melania, which she later released to the public. The tapes captured candid moments of the First Lady expressing frustration about her public image and the expectations of her role. The release of these recordings caused a national stir and was seen by many as a betrayal, while others argued it was a bold and necessary exposé.
Despite everything, Stephanie has insisted that her intentions were not revenge-driven. She said she felt used and discarded by Melania and wanted to tell her side of the story. In the book and media appearances, she expressed sadness over the loss of a friendship she once deeply valued. She described their bond as like sisters—until trust was broken.
In essence, Stephanie Winston Wolkoff was not just Melania’s best friend—she was her confidante, advisor, and almost like extended family. Their relationship offered a rare window into Melania’s inner world, a place few had access to. It’s a story of loyalty, ambition, and ultimately, betrayal. Not a singer, not an actress—but in the drama that played out on the national stage, Stephanie Winston Wolkoff became a central figure in Melania Trump’s life story.
