Melania Trump, the former First Lady of the United States, is known for keeping a relatively private and reserved circle of friends. Among the few individuals closely associated with her, one name stands out prominently: Stephanie Winston Wolkoff. Although their friendship has since soured, for many years she was considered one of Melania Trump’s closest confidantes and best friends.
Stephanie Winston Wolkoff is not a singer or an actress, but she is a well-known figure in the world of fashion and event planning. She worked as a high-profile executive at Vogue magazine and helped produce the annual Met Gala—one of the most prestigious fashion events in the world. Later, she became involved in planning the inauguration festivities for Donald Trump in 2017. Her career background is rooted in public relations, event production, and luxury branding, which aligned well with Melania Trump’s elegant and fashion-conscious image.
Wolkoff and Melania met in the early 2000s through mutual connections in New York’s social scene. They bonded over shared interests in fashion, lifestyle, and their experiences navigating elite circles. Over time, their friendship deepened, with Wolkoff reportedly becoming one of Melania’s most trusted advisors, especially during the early days of Donald Trump’s presidency.
When Trump won the 2016 election, Stephanie was brought in to assist with inaugural planning, and she later served as an unpaid senior adviser to the First Lady. At the time, this was seen as a natural extension of their friendship—Melania was said to trust her implicitly, valuing her discretion and judgment. Stephanie was often by Melania’s side, helping shape the image of the new First Lady and providing behind-the-scenes support.
However, their friendship took a dramatic turn in 2018. A scandal emerged involving the finances of the Trump inauguration, particularly concerning how funds were spent. While no legal wrongdoing was ultimately attributed to Wolkoff, scrutiny and media attention increased. As a result, she was let go from her role as an adviser, reportedly feeling scapegoated by the Trump administration.
Following the fallout, Stephanie Winston Wolkoff released a book in 2020 titled Melania and Me: The Rise and Fall of My Friendship with the First Lady. The book details their relationship, offering a behind-the-scenes look at Melania’s life in the White House and shedding light on her personality and private conversations. Most notably, Wolkoff secretly recorded some of her conversations with Melania, which were later released publicly. These recordings stirred controversy, as they revealed Melania’s candid opinions on topics like Christmas decorations and her role as First Lady.
The release of the book and tapes marked the definitive end of their friendship. Melania Trump and her team dismissed Wolkoff’s claims, calling her a disgruntled former friend seeking attention and profit. Critics and supporters alike debated the ethics of Wolkoff’s actions—while some praised her for revealing the truth, others criticized her for betraying personal trust.
Despite the bitter end, there is no denying that Stephanie Winston Wolkoff once played a significant and influential role in Melania Trump’s life. For over a decade, she was more than a professional associate; she was a close companion, advisor, and confidante. Their friendship, though now fractured, was emblematic of Melania’s limited but carefully chosen social circle. Wolkoff’s insight into Melania’s world provides a rare glimpse into the life of a woman who remains largely enigmatic, even after serving as First Lady.
In short, while Melania Trump may now prefer solitude and privacy, there was a time when Stephanie Winston Wolkoff was arguably her best friend—a relationship marked by shared ambition, loyalty, and ultimately, public betrayal.
