Trump famously cheated on his first wife with actress Marla Maples before divorcing Ivana for her. Before the divorce, he kept his mistress Maples close, even flying her to him in Aspen while there with his family. His affair was heavily reported in tabloids of the time.

Trump also cheated on his third wife Melania with porn actress Stormy Daniels a month after she gave birth to his fifth child.

The Atlantic – Donald Trump’s Very 1990s Tabloid Scandal
Newsweek – Donald Trump’s divorce: Marla Maples, Ivana and the split that gripped New York
Business Insider – Tabloid covers from the ’90s show the insanity of Trump’s divorce from ex-wife Ivana