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Integrity. Accountability. Trust. Responsibility. These are all traits that have been exemplified by some of America’s greatest leaders. And while the country stands divided on which of these (if any) can be found in Donald Trump, he does share someting with a few of his predecessors: a penchant for sexual indiscretion. From Jefferson to Roosevelt, Cleveland to Kennedy, salacious scandals might be the only thing the parties have in common. It has long been documented that the president fancies himself a ladies' man — his not-so-little black book may boast more names than the Declaration of Independence. We may never know the number of women that #45 has wooed, but commenting on his mistresses wasn’t something he was always so tight-lipped about. Here is a chronological list of some of Trump’s more public affairs.
Affair: 1989-1992
Married: 1993-1999
Marla Maples is a television personality and actress known for her work in Executive Decision (1996), For Richer and Poorer (1997), and more recently, A Nanny for Christmas (2010). She was married to Donald Trump from 1993 to 1999, but before she was his second wife, she was his mistress. Having moved to New York in 1985, she began her affair with Trump in 1989 after serendipitously meeting him on Madison Avenue. Their shocking romance achieved tabloid infamy when it was reported that Trump’s then-current wife, Ivana, confronted Maples in Aspen, Colo., after Trump had secretly flown her out during the family’s 1990 Christmas trip. Following his divorce from Ivana in 1992, Trump married Maples in December 1993, but their relationship would ironically end in the way that it began. In April 1996, a cop stumbled upon Maples and Trump’s bodyguard at 4 a.m., underneath a lifeguard stand in Palm Beach. Long story short — bodyguard was fired, and Maples’s divorce was finalized in 1999. Maples and Trump share one daughter, Tiffany, who was born in 1993.
Affair: July 1989
Gabriela Sabatini is a former professional tennis player from Argentina. She has won titles at the U.S. Open and Wimbledon, and even has a silver medal from the 1988 Seoul Olympics. It is safe to say that Trump was a fan of her one-handed backhand, as the two had a Grand Slam of their own back in 1989. Then 19, Sabatini dated Trump while he was still married to Ivana and on a break from mistress Marla Maples. The relationship ended after one month, which is assuredly for the best. Sabatini went on to have an extremely successful career, culminating in her induction into the International Tennis Hall of Fame and release of her best-selling perfumes.
Affair: 1993
Once upon a time in 1990, 26-year-old model Rowanne Brewer Lane met Donald Trump at a Mar-a-Lago pool party. As he showed the 1988 Miss Maryland around the ostentatious estate that would later become the "Winter White House," he graciously offered the “Best Body on the Beach” winner a swimsuit, because she had forgotten to change after an earlier photo shoot. The pair went on to date in 1993 (while Trump was tied to Maples), before ending the affair amicably a few months later. She shares a daughter with Warrant lead singer Jani Lane.
Affair: 1995
Kiwis may not be on the menu at Trump Grill, but that didn’t stop Donald from rendezvousing with one back in 1995. Kylie Bax is a New Zealand-born Sports Illustrated model and actress known for her work in Storm Catcher (1999), The Big Tease (1999), and Get Over It (2001). The whirlwind, hush-hush romance must have left a fond impression on Bax, as she endorsed Trump during his 2016 presidential campaign.
Affair: December 1997
Not all stories are riveting. Allison, a 27-year-old (you guessed it) model, met Donald Trump in December 1997 while he was separated from wife Marla Maples. They went on three dates, and that was that!
Affair: 1998
On the other hand, Kara Young’s tale of being a Trump mistress is as messy as they come. Posing for Victoria’s Secret, Playboy, and Vogue, Young had a face that could launch a thousand ships — relationships, that is. She met Trump at a party in the Hamptons in 1997 while he was still separated from Marla, and they dated until 2000. At the time, however, she was engaged to celebrity gossip columnist A.J. Benza, a fact that surfaced in a notorious segment of The Howard Stern Show.
Affair: June 2006 – April 2007
Playmate Karen McDougal met Donald Trump at a Playboy Mansion party that Hugh Hefner was hosting in 2006. They stayed in touch, and she ended up dating him secretly for 10 months, just a year after he and a pregnant Melania tied the knot. In order to keep the romance discreet and avoid a paper trail, Trump would have McDougal pay for her own travel and lodging and then reimburse her with cash in person. Unfortunately, a “paper trail” is what ultimately led to the outing of the affair. Before the 2016 election, American Media Inc., which owns the Trump-allied National Enquirer, paid McDougal $150,000 for the rights to her story in an attempt to buy the account and bury it. Handwritten memoirs from McDougal were passed to The New Yorker’s Ronan Farrow by a friend of hers, which kick-started the media maelstrom currently surrounding the whole affair. Recently, McDougal reached a settlement with American Media nullifying her original nondisclosure agreement and allowing her to spill the tea on everything.
Affair: July 2006
Years go by and people grow and mature, unless you’re Donald Trump. When you’re Donald Trump, you keep doing the same thing that gets you in trouble, but you just deny it when you’re caught. Enter Stephanie Clifford, a.k.a. Stormy Daniels — easily the most polarizing figure making waves in the political news world. Trump met the adult film star at the Edgewood Tahoe Golf Course in July 2006. Inviting Daniels back up to his room to see the AVN Best New Starlet’s work firsthand, the future president allegedly initiated a months-long affair with the rising actress (though they only had sex that one time, Daniels says). In 2011, reports of the affair began to circulate after The Dirty and Life & Style magazines published their own versions, with In Touch Weekly choosing to woodshed its Daniels interview after lawsuit threats by Trump’s attorney Michael Cohen. In January of this year, it came to light per Wall Street Journal reporting that Cohen paid Daniels $130,000 a month before the 2016 election through a company he had just created, barring her from speaking of the affair. Inadvertently, Cohen’s disclosure of the transaction breached the agreement, allowing Daniels to freely talk about how Trump likes to get spanked with a Forbes magazine.
