Stephanie Winston Wolkoff: 5 Things About Former Melania Trump Advisor Who Taped First Lady

Stephanie Winston Wolkoff wrote an explosive tell-all about former BFF Melania Trump, giving readers insight into FLOTUS’ life behind the scenes. Here’s what you should know about the former advisor herself.

Stephanie Winston Wolkoff is the name on everyone in DC’s lips after First Lady Melania Trump‘s former friend and advisor published a juicy tell-all book about the White House behind the scenes. After publishing Melania and Me: The Rise and Fall of My Friendship with the First Lady, Winston Wolkoff has revealed even more intimate details about her time in the East Wing, and beyond. Here’s what you should know about her:

1. She and Melania Trump became friends in 2003. Back then she was still Melania Knauss, the model girlfriend of future President Donald Trump. The two became close, and Winston Wolkoff and her husband, real estate developer David Wolkoff, would even go on double dates with the Trumps. The two women had monthly lunches at the Mark Hotel in Manhattan and the Wolkoffs would vacation at Mar-a-Lago, according to Melania and Me, and their friendship continued when the Trumps made their move to DC. Before the election, Winston Wolkoff vehemently defended her friend in the press. She told Dujour in 2016, “Don’t underestimate her just because she is quiet and reserved… she’s very confident in her viewpoint.”

2. She served as an unofficial advisor to the First Lady until February 2018. Winston Wolkoff took her expert event planning experience to the White House in 2017, serving as executive producer of Trump’s presidential inauguration. From there, she served as FLOTUS’ confidant, advisor, and somewhat of a protector, helping her craft her new image as First Lady. She helped Trump create her Be Best initiative and even suggested which designers she should wear, according to Melania and Me.

The cozy working relationship, and friendship, ended in February 2018, though, after The New York Times reported that her company, SWW Creative, had been paid $26 million by Trump’s inauguration committee. Winston Wolkoff vehemently denies this. “Was I fired? No,” she told the outlet in 2019. “Did I personally receive $26 million or $1.6 million? No. Was I thrown under the bus? Yes.” After her departure from the White House, the First Lady apparently sent her an apologetic email, saying that she was “confident” that their friendship “far outweighs politics.”

Stephanie Winston Wolkoff Book
The cover of Melania and Me. The photo was taken onboard Air Force One by her daughter, Alexi Winston Wolkoff. (Courtesy of Simon & Schuster)

3. She’s the former director of special events at Vogue. That means that Winston Wolkoff was in charge of organizing the annual Met Gala. She and Melania actually met at Vogue, where Andre Leon Talley, Vogue‘s editor-at-large at the time, reportedly helped give the future First Lady a high society makeover before her official debut as Donald’s girlfriend. Anna Wintour reportedly nicknamed her “General Winston” during her time at Vogue because of her reputation for hustling, according to The New York Times.

4. She secretly recorded conversations with the First Lady for her book. At first, she wouldn’t confirm there were tapes, instead saying in an interview with ABC on August 31 that she “can back up everything that’s in the book, 100 percent.” The following day, she told MSNBC that she did have tapes. “Melania and the White House had accused me of criminal activity, had publicly shamed and fired me, and made me their scapegoat,” Winston Wolkoff said to Rachel Maddow. “At that moment in time, that’s when I pressed record. She was no longer my friend and she was willing to let them take me down and she told me herself that is the way it has to be.”

Stephanie Winston Wolkoff
Stephanie Winston Wolkoff (McMullan/Sipa USA)

5. She has famous family members. Winston Wolkoff’s brother is For Keeps actor Randall Batinkoff. Her mother’s second husband, who adopted her at age 26, is Bruce Winston, the son of famed jeweler Harry Winston.

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