There was a time not terribly long ago, before the hush money payouts, white nationalist equivocating, child separations, dictator-courting, and yield curve inversion, when Donald Trump moonlighted as a pop culture obsessive. He would call in to deliver morning-after Oscars recaps on Fox & Friends, always taking issue with the host and décor; engage in “locker-room talk” with Howard Stern, with the two man-children regularly rating famous women’s looks on a scale of 1-10; and tweet—and tweet, and tweet—about celebrity breakups. (He weighed in on the Kristen Stewart-Robert Pattinson split 11 times. He was 66 years old.)

When he wasn’t posting-and-toasting or bossing around D-listers on The Celebrity Apprentice, Trump would pass the time filming short Vine videos (R.I.P. Vine) from his work desk in Trump Tower, ranting about, say, the announcement of an all-female Ghostbusters reboot or Sacha Baron Cohen dumping ashes on Ryan Seacrest at the Oscars. On Aug. 29, 2013, Trump tweeted a link to a Vine video, along with the caption: “A message for my hotel guest, @MileyCyrus.” In the accompanying clip, the real estate heir bellowed into the camera, “Miley, don’t let ‘em get you down. They’re all jealous.”

The reality TV host and future president was of course referring to Cyrus’ controversial performance at the 2013 MTV Video Music Awards—The Twerking Seen ‘Round the World. It initially took on the guise of a bad acid trip, with Cyrus sticking her tongue out a whole lot and dancing with some teddy bears whilst performing new single “We Can’t Stop.” Then, the 20-year-old ex-Disney starlet stripped down to a nude-colored latex two-piece, and was joined by Robin Thicke for a rendition of “Blurred Lines.” The inherent creepiness of that song notwithstanding, Cyrus proceeded to lick, prod, grind up on, and twerk against Thicke, to cheers from the adoring fans in the pit and confused looks from the A-listers in attendance.

Though the “Blurred Lines”/twerking bit lasted just over a minute, and was relatively tame by 2019 standards, it was all anyone (over 40) could talk about the next day. And they were outraged. Over on Fox & Friends, a network that consistently sucks up to a man who’s been accused of sexual misconduct by over 20 women, guest co-host Anna Kooiman said, “This was just raunchy. This wasn’t sexy. There wasn’t any talent.” Real Time host Bill Maher tweeted, “Watching VMAs. Haven’t been in a strip club in a while, but good to see nothing has changed.” And MSNBC co-host Mika Brzezinski got very irresponsible very fast, claiming, “That young lady, who is 20, is obviously deeply troubled, deeply disturbed. Probably has confidence issues, probably an eating disorder. And I don’t think anybody should have put her up on stage. That was disgusting.” Yikes.

Trump—who again was 66 years old at the time—was particularly taken by the 20-year-old’s gyrating, think piece-generating turn. In fact according to Cyrus, in addition to his tweet and Vine video, the lecherous mogul phoned the pop star’s hotel room to personally tell her just how much he enjoyed the performance. “I was staying at the Trump Hotel and Donald Trump literally called and said, basically, ‘I know everyone’s talking about it, but I loved it,’” Cyrus later recounted to The New York Times.

She added, “Even people around me really judged me. People that I really loved and thought were my friends judged me for it. They were like, ‘You were on drugs when you did that performance.’ I did nothing! I still don’t get it… When you look at it now, it looks like I’m playing hopscotch. Compared to what I do now, it looks like nothing. I can’t believe that was a big deal. It wasn’t shocking at all.”

Over the next few weeks, Trump would tweet about Cyrus a total of eight times. They began with Trump coming to Cyrus’s defense, questioning a Twitter user who accused her of racism, telling her she could “do much better” following her split from actor Liam Hemsworth, and proclaiming that she is “a really good person.”

Then, as with all matters Trump, things took a sharp turn. At 1:48 a.m. on Sept. 24, the thrice-divorced sexagenarian slut-shamed Cyrus over her choice of attire, writing, “I am a defender of @MileyCyrus, who I think is a good person (and not because she stays at my hotels), but last night’s outfit must go!” Ten minutes later, he added, “@MileyCyrus is on a very triky [sic] and slippery path right now. The right moves will lead to greatness, the wrong moves to oblivion! GUIDANCE.”