Before there was Gigi and Kendall… before there was Karlie and Taylor… there was Anna Wintour and Donald Trump. Yes—back in the day, the Vogue editor-in-chief and POTUS were close enough buds to rival some of the most inseparable friendships in Hollywood. Their friendship can be traced back as early as 1990 when Wintour was spotted at the 41st birthday of Trump’s then-wife, Ivana.
Since then, Wintour has been a recurring guest at Trump family gatherings. She’s attended galas with Trump’s niece, Blaine; she’s attended store openings at Trump Towers; she’s sat next to the president himself at runway shows; and she’s even offered Trump’s daughter, Ivanka, a post-grad job at her magazine. (Despite pushing from her father, Ivanka ended up turning the offer down.)
But, in spite of Trump and Wintour’s thick-as-thieves friendship in the ’90s and early 2000s, the pair has seemed to drift apart in recent years—right around the time Trump’s career shifted from reality TV boss to political candidate. In October 2016, Vogue endorsed Trump’s competitor, Hillary Clinton, calling her “optimistic, forward-looking, and modern.” In December, Wintour was overheard ranting about Trump on a “packed commuter train” in New York City. “Trump’s foundation has done nothing,” she reportedly said. “Its board is packed with relatives, and he’s going to use his presidency to sell himself and his brand and profit personally for himself and his family.
Still, Trump and Wintour’s friendship remains complicated. After news broke of her anti-Trump remarks, Wintour apologized. “I immediately regretted my comments, and I apologize,” she told The Mirror. “I hope that President-elect Trump will be a successful president for us all.” Not too long after, there came a mysterious meeting between Trump, Wintour, and Kanye West at Trump Tower. The details of its purpose are still murky, though West reported they discussed topics including bullying, teachers, and supporting schools in Chicago.
While we have no idea where Trump and Wintour stand today, we have a feeling their friendship is just as complex and rocky as any other frenemy relationship in Hollywood. And while we wait for more clues about whether they’re on the ins or the outs now that Trump’s administration is doing things like ending DACA and blocking efforts to close the pay gap, we figured we might as well analyze photos of when Wintour and Trump hung out in the past. Check them out, below.