Trump Family's Extramarital Affairs in 8 Clicks: Donald's 'Playboy Image' to Don Jr.'s Relationship With Aubrey O'Day

Donald Trump has maintained his "playboy image" while dealing with affair rumors. In the 1991 book Trump, The Greatest Show on Earth: The Deals, The Downfall, The Reinvention, author Wayne Barrett looked back at the time the ex-president tried to get Playboy to do a "Girls of Trump" spread.

The idea had Trump woo "his most shapely staffers, including a former beauty queen secretary, into posing for the magazine with a sliding scale of offers on everything from full nude to b----- to 'wet-lip' shots."

"It was all part of the rakish ethos of phony glamour that he consciously fostered, even to the extent of concealing from public view a very efficient secretary with a pimplish facial condition," Barrett continued.

Over the years, at least 26 women also came forward with allegations against Trump, claiming the 2024 presidential candidate sexually assaulted them between the 1970s and 2016.

Donald wed his first wife, Ivana Trump, in 1977. Their marriage fell apart when his affair with model Marla Maples emerged.

Two years after Ivana and Donald divorced in 1991, the ex-POTUS tied the knot with Marla. They welcomed their daughter, Tiffany, in 1997, the same year they announced their divorce.

He did not stay single for a long time as he met Melania Trump, whom he married in January 2005, in 1997 and started pursuing her.

After years of dealing with accusers, Donald was slapped with another headache when the Wall Street Journal released a 2018 story about his personal lawyer, Michael Cohen, paying adult film star Stormy Daniels before the 2016 election. Cohen pleaded guilty to eight federal crimes in August 2018.

Donald broke his silence for the first time regarding the issue in a 2018 conversation with reporters aboard Air Force One, saying he did not know anything about the hush money payment. He addressed it again during his interview with Fox and Friends.

"He represents me — like with this crazy Stormy Daniels deal he represented me," Donald said. "And, you know, from what I see he did absolutely nothing wrong. There were no campaign funds going into this… which would have been a problem. Because he's got other things. He's got businesses, and from what I understand they're looking at his businesses, and I hope he's in great shape."

A year after a New York grand jury voted to indict Donald, the 78-year-old businessman surrendered and went through a trial in a Manhattan federal court. A jury found him guilty of 34 felony counts of falsifying business records to cover up the hush money payment.

In an interview with CNN's Anderson Cooper, former Playboy model Karen McDougal alleged she had a 10-month affair with Donald years after their meeting at a Playboy Mansion party.

McDougal claimed she visited Donald several times and that he brought her to Trump Tower.

"We went into the back entrance, and at that point I realized where we were going, and I said, 'Aren't you afraid to bring me here?' He's like, 'They won't say anything.' I'm like, 'OK.' So, we went upstairs and we looked around," said the model.

The affair allegedly happened before Barron Trump's birth in June 2006.

More accused Donald of sexual harassment and inappropriate behavior, which reportedly happened during his relationship and marriage to Melania.

Former People writer Natasha Stoynoff alleged that Donald pushed her against a wall when she went to Mar-a-Lago in December 2005 to interview him and Melania, who was pregnant at the time. The media personality reportedly "shoved" his tongue "down her throat" during the incident.

In 2006, Donald allegedly assaulted and harassed several Miss Universe and Miss USA contestants.

Aubrey O'Day has been vocal about her alleged affair with Donald's son Donald Trump Jr. She called Don Jr. her ex for the first time when she appeared on the season premiere of Ex on the Beach. She also referred to him as her soulmate.

The infidelity reportedly ended when Vanessa Trump discovered their text messages.

On Michael Cohen's "Mea Culpa" podcast, the former Danity Kane member claimed she and Don Jr. had s-- for the first time in the bathroom of a g-- nightclub while he was still married to Vanessa.

Variety Editor-in-Chief Ramin Setoodeh's book, Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, also cited The Celebrity Apprentice contestant Clay Aiken's statement about the affair, saying it "was not a well-kept secret."

Clay said Aubrey revealed their relationship performance at an event in St. Petersburg, Fla.

In the same book of Setoodeah, the ex-president confirmed he was aware of the story about his son.

"When I ask Trump about O’Day’s affair with Don Jr., he takes a long pause. 'I had heard that, actually,' he says, blinking. 'No, I had heard that.' Did he know that O’Day had written a song about Don Jr.? 'I hadn’t heard the song. But I had heard that,' Trump says, confirming once again that he’s aware of the story about Don Jr. sleeping with one of the contestants on The Celebrity Apprentice," the excerpt read.

Reporter Carol Leonnig revealed in the book Zero Fail: The Rise and Fall of the Secret Service that Vanessa and Tiffany Trump became "inappropriately close" with the Secret Service agents.

One of the agents said Vanessa had "started dating one of the agents who had been assigned to her family." Meanwhile, Tiffany reportedly built a connection with another security after a breakup and started "spending an unusual amount of time alone" with him.

A spokesperson for Tiffany told the Post that the relationship was "entirely professional."