Melania Trump's Former Friend Sheds Light on Her Relationship With Ivanka

A new book has said Melania Trump's infamous "I really don't care, do u?" jacket that she wore when visiting a detention center was aimed at stepdaughter Ivanka Trump—but Stephanie Winston Wolkoff has rubbished the claim.

Winston Wolkoff was formerly an aide and close confidant of the ex-first lady and was Melania Trump's first hire after Donald Trump's 2016 election victory. However, their friendship ended following reports that Winston Wolkoff benefited handsomely as a contractor for the 2017 inauguration.

According to the New York Post—which cited the book American Woman: The Transformation of the Modern First Lady, from Hillary Clinton to Jill Biden by Katie Rogers—Melania Trump allegedly resented Ivanka's efforts to supplant her role and take over the White House's East Wing.

Melania Trump and Ivanka Trump
Left, Melania Trump is seen in the Rose Garden of the White House in Washington, D.C., on November 24, 2020. Right, Ivanka Trump attends the grand opening of Fontainebleau Las Vegas on December 13, 2023,... Chip Somodevilla/Ethan Miller/Getty Images

Winston Wolkoff has denied this claim. She has also denied the idea that Melania Trump wore the jacket because she and Ivanka Trump were locked in a battle for press coverage, which former Trump administration officials are alleging.

Newsweek contacted a spokesperson for Melania Trump and Ivanka Trump via email Thursday.

"Melania Trump was NOT sending a message to Ivanka," Winston Wolkoff posted to X on Sunday. "Being Melania's best friend for over a decade, I learned the hard way how soulless she really is & how she used me for my connections & experience. Others can say whatever they 'think' they know to be true. The truth matters always."

Winston Wolkoff explained her post in a statement shared with Newsweek, in which she also criticized Rogers.

"I wrote about this story extensively in my book Melania and Me, The Rise and Fall of My Friendship with the First Lady from a direct conversation I had with Melania about it," she said. "Melania and Donald Trump weaponized the DOJ against me by having Jeffrey Clark sue me to try and silence me so the truth and the facts about this, them, and so much more wouldn't be shared with the American people."

Winston Wilkoff claims that former aide Stephanie Grisham and Rogers have "recycled" stories from her life for the new book.

"After all these years and with another election around the corner, I would have thought Grisham would have come clean about how she lied about me to the media," she said. "I continue to speak up because I want people to know how deceitful and deceptive the Trump family is and it doesn't matter who you are.

"Each and every one of their allies who haven't come forward and spoken the truth are not immune from their betrayal. They will one day turn on them and the destruction they leave behind is life-shattering."

Melania Trump and Ivanka Trump's relationship has been called into question numerous times in the past but in 2019, Ivana Trump—the first wife of Donald Trump, and mother to Ivanka, Donald Jr. and Eric—said her daughter liked the former president's current wife.

"She likes her fine. Because she didn't cause me to break up the marriage like the other one—I don't even want to pronounce her name," she said in a report published in The Atlantic.

"The other one" she refers to is Marla Maples, who had a relationship with Donald Trump for several years before she became his second wife in 1993. That marriage ended in divorce in 1999.

This isn't the first time that Winston Wolkoff has issued less than flattering assessments of her former boss.

During an appearance on CNN NewsNight, host Abby Phillip asked whether the former first lady would be making more appearances in the coming months to help Donald Trump's 2024 presidential campaign. Winston Wolkoff said: "I do feel strongly that Melania Trump isn't going anywhere. I believe that Melania will stay by Donald's side. Throughout all of this, she is his partner in crime."

She also claimed her former friend is "exactly like Donald" when it comes to courting publicity.

"Unfortunately, people keep giving her this out, this reason to believe that Melania should be freed from Donald, but Melania is complicit," she told Phillip. "Melania is, you know, side by side with the showmanship and she is exactly like Donald, just, unfortunately, in a skirt and high heels, and showing up today was just another way for her to have some camera time."

In February 2018, Melania Trump cut ties with Winston Wolkoff after news broke that her event planning company, WIS Media Partners, received $26 million to help coordinate Donald Trump's inauguration.

In Winston Wolkoff's 2020 book Melania and Me, she said she resigned because the Trump administration scapegoated her. She has also denied claims that she personally received $26 million.

Update, 02/29/2024 10:33 a.m. ET: This article was updated with comment from Stephanie Winston Wolkoff.

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