22 Photos of the Trump Family’s Many Years Attending the Met Gala

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The Trump family didn’t just used to be invited to the Met Gala — they used to be the backbone of exactly who Anna Wintour and her event-planning cohorts wanted there. Case in point: Stephanie Winston Wolkoff, longtime lead organizer of the Met Gala and fashion director for New York Fashion Week, was Melania Trump’s close friend and confidante until her brief stint as the First Lady’s advisor resulted in a shattered friendship and tell-all book Melania and Me: The Rise and Fall of My Friendship With the First Lady. In her book, Wolkoff opens up not just about what led to the dissolution of their relationship but of the particular pride the Trumps took in their Met Gala association over the years — and what happened when those invite calls stopped coming.

“In 2010, in order to give them the best possible seats, I hosted Donald and Melania at my table at the Met Gala,” Wolkoff recalls. “As soon as Donald sat down, he asked, ‘Where’s Anna’s table?’ Real estate was everything to him, and if he wasn’t seated close enough to Anna, well, he wasn’t happy about it.”

“People who could easily afford to buy tickets begged to purchase them, but it was by invitation only,” Wolkoff recalls of her nine years running the event. “Donald always stuck to the minimum with two $1,500 individual tickets — the cheapest available — as did his daughter Ivanka.”

When Donald wanted to propose to Melania in 2004 after five years of dating, Wolkoff says he knew the Met Gala would be the perfect place to announce the news. He proposed that evening and Melania wore out the $1.5 million sparkler to cement her status as a member of high society now that she was Donald’s wife-to-be, a series of steps Wolkoff recounts as being planned to a tee.

“Donald knew that the party inside the museum wasn’t nearly as important as the stairs leading into it. That stretch of Fifth Avenue on the first Monday in May is priceless real estate. If you were seen and photographed there, you were “in”..That was a matter of fact,” she recalls. “Having invested only $3,000 in tickets, Donald would get invaluable and priceless publicity, using the paparazzi and journalists covering the red carpet to bestow superhuman power on him — and his woman — as they ascended the steps.”

So, what happened when the event that made them no longer wanted them around? “In 2013, I got a call from Melania’s assistant asking me to make a call to get the Trumps invite-only tickets to the Met Gala. Didn’t she know I hadn’t produced the event in years?” Wolkoff writes. “I couldn’t help her. A few weeks later, I followed up and asked what she was wearing to the event, and she said, ‘We decided not to attend.'”

Ivanka enjoyed a longer run on the Met Gala red carpet than father Donald and his third wife, continuing to show up in 2013, 2014, 2015, and even 2016 to the Vogue-run event with Jared Kushner on her arm and an increasing shadow of controversy billowing around her. From 2003 to that final year of Trump attendance, 2016, read on for photos of all the Trump family members who were once a mainstay of the Met Gala red carpet.

A version of this story was originally published in 2021.