In a 1989 cover story for Time Out, Madonna attends a boxing match at Trump Hotel and Casino in Atlantic City, but as she enters the building with then-husband Sean Penn, she is met with a flurry of photographers. She blames the lack of privacy and security on Trump himself. 'Where am I supposed to go? What am I supposed to do? I can't believe Donald Trump,' she said at the time. She also played a sideline role in the Mike Tyson and Michael Spinks contest, with her face appearing prominently on a ringside 'Wanted' poster. Later in the story, she and Trump get into a bit of scuffle as he suggests she take better seats even though she doesn't want to leave behind her guest - the journalist accompanying her - all alone.
The concept of Trump becoming president was presented to Madonna back in 1990 during a conversation for Interview Magazine when the then–real estate scion was first floating the idea of running. 'With Marla? But he can't be president if he's had sex. That's the rule,' she joked. The interviewer mentioned the now-POTUS' desire to be like JFK and having to 'prove that he's a womanizer.' When the interviewer suggests that Trump has an 'aura of power,' Madonna is dismissive. 'He's a wimp,' she responded, before alluding to the country's tendency to cycle between choosing family men and 'a guy with a dick,' as the singer put it, for the office. 'Couldn't we get someone more handsome?' she adds.
Trump, seeming to have forgotten that Madonna publicized her lack of attraction towards him, decided to link the two in the news once more a year later. At the time, Trump was dealing with tabloid gossip that claimed that he had broken up with Marla Maples. People's Sue Carswell called his office and spoke to a man named 'John Miller' who claimed he was Trump's publicist. 'Miller' told Carswell that 'important, beautiful women' like Madonna called his 'client' all the time, asking him out. Both an associate of Trump and Maples confirmed to Carswell that John Miller was in fact Trump himself.
March on Washington - and the Aftermath
At the Women's March, Madonna gave an empowering speech to the hundreds of thousands of attendees. One line, however, drew ire from conservative websites that focused on the violent nature of her words: 'Yes, I'm angry. Yes, I am outraged. Yes, I have thought an awful lot about blowing up the White House. But I know that won't change anything. We cannot fall into despair.' Madonna later clarified that she meant to examine the difference between feeling hope and despair in response to the election, noting that her words were intended as a metaphor and that she never aims to promote violence. Newt Gingrich told the press that she should be arrested, and a radio station in Texas has stopped playing her songs because of her 'un-American sentiments.' As he is wont to do, Trump also responded to his critic during an interview with Sean Hannity for Fox News. 'She's disgusting,' he said. 'I think she hurt herself very badly. I think she hurt that whole cause. I thought what she said was disgraceful to our country.'