Melania Trump's former top aide is campaigning her new TV show
Stephanie Winston Wolkoff, Melania Trump's former top aide, is campaigning across New York City for her new streaming series "The Trouble with Billy," telling Page Six she refuses to be defined by her abrupt White House exit or the inauguration-funding fallout that ended her East Wing advisory role. The Vogue alum and memoir author is pivoting from politics to Hollywood production, framing the fictionalized drama as a story about second chances that mirrors her own reinvention.
Key Takeaways
- Stephanie Winston Wolkoff, once Melania Trump's closest East Wing confidant, is executive producing "The Trouble with Billy" on Red Coral Universe.
- She told Page Six that Melania Trump was "one chapter" of her life and that she wants to create stories beyond headlines and political betrayal.
- The show stars '90s heartthrob William McNamara and Billy Baldwin in a fictionalized account of McNamara's fall from fame amid addiction.
- Wolkoff was ousted after her firm received roughly $26 million for Donald Trump's first inauguration; she has called herself a scapegoat.
- She and McNamara have been making NYC appearances, including a salon visit with Hilaria Baldwin and a premiere party at Aquarelle.
Why is Melania Trump's former top aide promoting a TV show now?
Wolkoff told Page Six she is determined not to be defined by what she described as an unceremonious departure from the White House. "Melania was one chapter of my life. It's not my story," she said, referring to the first lady relationship she chronicled in a memoir about their friendship and the so-called FLO-TUS rift.
Her latest project marks a deliberate shift toward storytelling. After producing "Gunslingers," Wolkoff is now executive producing "The Trouble with Billy," a fictionalized series based on William McNamara, the '90s heartthrob who lost everything at the height of his fame, largely because of alcohol and drug abuse. Billy Baldwin and Wolkoff's brother Randall Batinkoff, who brought her onto the project, also star.
What is "The Trouble with Billy" about?
According to Page Six, the series dramatizes McNamara's rise and collapse during Hollywood's peak '90s era. Wolkoff said the material resonates personally: "I know something about rebuilding life after your worst chapter, and I know no one should be defined by a single moment."
The show streams on Red Coral Universe. Wolkoff and McNamara have been working the publicity circuit in Manhattan to build buzz ahead of and after its premiere, positioning the project as entertainment with a redemptive message rather than another political tell-all.
How did Wolkoff's White House role end?
Before Donald Trump ran for president, Wolkoff was a longtime confidant of Melania Trump. She joined the East Wing as an adviser once the Trumps arrived at the White House. Her tenure ended after reports that her firm received about $26 million for helping plan Donald Trump's first inauguration.
Wolkoff has maintained she was made a scapegoat and that she personally received only a fraction of that sum. The controversy overshadowed her advisory work and became the defining public chapter she now says she is trying to leave behind.
Where has Wolkoff been spotted while campaigning the series?
Page Six reported that Wolkoff and McNamara were seen at Eliut Rivera's salon earlier last week, where they connected with Hilaria Baldwin. Last Thursday, they co-hosted a joint celebration with Noel Ashman at Aquarelle, marking both his birthday and the premiere of their show.
"I don't want to be defined by politics or betrayal," Wolkoff told the outlet. "I want to spend my time creating stories that remind us to look beyond the headline, believe in second chances and never lose sight of the person behind the public image." For more updates on Trump-world figures crossing into entertainment, follow our Celebrity Breaking News coverage. Page Six first reported the campaign push in its June 29, 2026 story.