Spending time with your pregnant wife is a perfectly decent way for a husband to behave, although that's not necessarily the case when you're hanging together at an infamous monument to hedonism. But that's just one strange detail in Don Jr. and Vanessa Trump's marriage.
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00:00Spending time with your pregnant wife is a perfectly decent way for a husband to behave,
00:04although that's not necessarily the case when you're hanging together at an infamous monument
00:09to hedonism.
00:10But that's just one strange detail in Don Jr. and Vanessa Trump's marriage.
00:15Donald Trump Jr. and his ex-wife, Vanessa Trump, didn't exactly have a magical first
00:19encounter when they met in 2003.
00:21According to Vanessa, it wasn't love at first sight.
00:23As she recounted to The New York Times in 2006,
00:26"'I'm at this fashion show.
00:28Donald Trump comes up to me with his son,
00:29"'Hi, I'm Donald Trump.
00:31I wanted to introduce you to my son, Donald Trump, Jr.'
00:34They then struck up a short, uncomfortable conversation before the show started, only
00:38to have Donald Sr. try to reintroduce them again a second time.
00:42As Vanessa explained,
00:43"'Donald comes back up to me again,
00:44"'I don't think you've met my son, Donald Trump, Jr.'
00:47She then responded,
00:48"'Yeah, we just met.
00:49Five minutes ago.'"
00:50Weeks later, Don Jr. and Vanessa ran into each other again, while out with mutual friends.
00:55They talked for an hour, initially not remembering their awkward first meeting until it later
00:59dawned on them and became something to bond over.
01:02Still, Don Jr. wasn't thrilled about his father playing matchmaker, as he admitted,
01:06"'It wasn't really my MO to have my father try to pick up girls from me.'"
01:11It didn't take long for Don Jr. to pop the question to Vanessa.
01:14It might have helped that he reportedly got his engagement ring for free, thanks to a
01:17promotional deal from the jewelry dealer Bailey, Banks & Biddle.
01:21It was in November 2004 when he got down on one knee in the Short Hills Mall in New
01:25Jersey and asked Vanessa for her hand in marriage.
01:28TV crews and paparazzi photographers were reportedly the only ones allowed to witness
01:32the moment.
01:33Despite the arguably tacky setting, the bride-to-be was all smiles, showing off her four-carat
01:38emerald-cut diamond sparkler worth $100,000.
01:42A representative for the jewelry dealer declined to comment on their agreement with Don Jr.,
01:47although an insider told the New York Post,
01:49It's probably the same kind of deal his father has with Graff.
01:51Graff has a lucrative product placement slot on The Apprentice.
01:55Donald Sr. scolded his son for the free ring decision during an interview on Larry King
01:59Live by declaring,
02:00"'You have a name that is hot as a pistol.
02:03You have to be very careful with things like that.'"
02:05The road to marriage for Vanessa Trump involved getting rid of some skeletons in her closet.
02:12A childhood friend of hers once told GQ that she used to date Valentin Rivera, a convicted
02:17criminal who was allegedly a member of the street gang, the Latin Kings.
02:21Rivera himself confirmed the rumors to Page Six, sharing dozens of letters Vanessa sent
02:26him during their five-year relationship, which began when she was 15 and continued into his
02:30prison sentence.
02:31As she wrote in one letter dated 1993,
02:34"'My 18th birthday.
02:35You'll be back in my arms.
02:37My prom.
02:38And I want to get pregnant and have a baby with you after January.'"
02:41Vanessa reportedly even visited Rivera at Rikers Island while he was serving time for
02:46assault.
02:47When Donald Trump Sr. reportedly found out about this chapter in her life and arranged
02:50for a meeting to discuss it, she then reportedly assured him that their family dynasty wouldn't
02:54be marred by any lingering gang ties.
02:58The Playboy Mansion probably isn't the first place you'd expect to run into an expectant
03:02mother.
03:03Nevertheless, as Donald Trump Jr. revealed in January 2007 when he was a guest on Adam
03:08Carolla's radio show, his pregnant wife tagged along with him to Hugh Hefner's former playground,
03:13and he wasn't exactly happy about that.
03:15As he recounted,
03:16"'Can you believe the hell I'm going through?
03:17I'm at the Playboy Mansion with a pregnant wife.
03:20It doesn't get worse than that, does it?
03:22Now I love my wife, but that is rough.
03:24And I'm going to pay for these statements later on tonight.
03:26I'm gonna pay.'"
03:27Donald Trump Jr. has a history of having a wandering eye, including public flirtations
03:32on social media.
03:33For example, model Melissa Stetton has claimed that he exchanged private messages with her
03:38in 2011, just a month after his wife gave birth to their third child.
03:41In 2018, Stetton tweeted,
03:43Surprised his marriage didn't work out since he was sending me DMs a month after his wife
03:47gave birth.
03:48This happened shortly after news broke that Don Jr. and Vanessa were divorcing.
03:52Stetton shared a screenshot of a private DM from Don Jr. that was a response to her tweet
03:56about pulling a muscle while removing a tampon, in which he wrote,
04:00"'While I'm getting s**t for the baking comment, glad I opted not to send the tweet asking
04:04for pics from your bathroom tweet last night.
04:06People need to chill.'"
04:07A spokesperson for Don Jr. claimed to People magazine that the interaction was a joke,
04:12but that wasn't how Stetton saw it.
04:13She shared another screenshot of a message from Don Jr. from 2011 that was a reply to
04:18a tweet of hers, in which she wrote that she planned to douse her body in bacon, one of
04:22his favorite scents.
04:23Along with a winking, smiley face, he reportedly wrote,
04:26"'Stop that.
04:27I'm a happily married man.'"
04:29Vanessa Trump filed for divorce in March 2018, right before Danity Kane's singer and reality
04:34TV personality, Aubrey O'Day, claimed to have had a year-long affair with Don Jr. after
04:39meeting him on the set of The Apprentice in 2011.
04:42According to Us Weekly, the affair ended when Vanessa discovered emails between the two
04:45of them.
04:46They ultimately decided to stay together at the time.
04:48In the aftermath of the divorce, O'Day began revealing details of the affair.
04:52During a 2023 interview on the Sophia with an F podcast, she claimed that at one point,
04:56Don Jr. was ready to leave Vanessa for her.
04:59It was,
05:00"'I'm leaving my wife and kids and this is gonna be what I want and I love you and you're
05:04my wife and everybody knows what it is.'"
05:07O'Day also claimed that Trump lawyer Michael Cohen helped bury news of the affair for years.
05:12Don Jr. has never publicly commented on the alleged affair.
05:16In October 2017, Donald Trump Jr. made his views about a certain political philosophy
05:20known on social media through somewhat questionable means.
05:23On Halloween, he shared a photo of his young daughter, Khloe, in a police outfit, holding
05:27a bucket of candy, along with the caption,
05:29"'I'm going to take half of Khloe's candy tonight and give it to some kid who's sad
05:32at home.'
05:33It's never too early to teach her about socialism."
05:35The photo and the remark got plenty of attention, including from Harry Potter author J.K. Rowling,
05:41who chimed in,
05:42"'Fill her bucket with old candy left by her great-grandfather.'
05:45Then explain that she has more because she's smarter than all the other kids.'"
05:48Overall, this comment was met with a mixed reception, though Don Jr. apparently remained
05:53unfazed, especially considering his reputation for making outlandish remarks.
05:57Either way, we hope that Khloe was able to sidestep her dad's political point-making
06:01and reap the rewards of her Halloween bounty.
06:03"'Give me that candy!''
06:06Don Jr. made a bold move in 2017 when he decided to relinquish his Secret Service protection.
06:11As reported by the Florida Times-Union, a close friend of his revealed that he wanted
06:15to give up the 24-hour security detail for himself, as well his wife and five children.
06:20Secret Service representative Katherine Mahoan declined to comment on the terms of the family's
06:24protection agreement.
06:26Insiders claimed that Don Jr. made the decision in order to lead a more private life, but
06:30it nevertheless posed serious risks.
06:32As Jonathan Wackrow, a former member of Barack Obama's security team, noted,
06:36In today's global risk environment, waiving this detail poses great danger to him and
06:40to his family.
06:41What he is becoming, potentially, is a target of opportunity.
06:44People who want to lash out at the president are going to seek that path of least resistance.
06:48This decision is negligent."
06:50As the free engagement ring story makes clear, Donald Trump Jr. isn't exactly known for being
06:55a big spender.
06:56In fact, he has a reputation for nickel-and-diming his way through life.
07:00According to Page Six, one of the reasons that Vanessa filed for divorce was her ex's
07:04cheap lifestyle.
07:05As an insider revealed, he gives her very little help and has been keeping her on a
07:09tight budget.
07:10She doesn't live a lavish life and can very rarely pick up a check at dinner.
07:13Sources also claim that Don Jr. treated Vanessa like a, quote, second-class citizen, and that
07:18she had to borrow money from her mother.
07:20However, her spokesperson debunked those allegations, insisting to Page Six,
07:23All of these claims are simply not true.
07:25Don and Vanessa have tremendous respect for each other and always have.
07:29The notion that she has had to rely on her family for assistance is absolutely false
07:33and utterly ridiculous.
07:35Insiders close to the couple told a different story, though, claiming that they lived separate
07:38lives for years.
07:40As one source told People magazine in 2018,
07:42Even before all this Trump presidency stuff started, they weren't good, and their marriage
07:46was strained.
07:47There's been speculation that Vanessa inherited a large fortune after her father's passing,
07:52and that this made it easier for her to finally divorce Don Jr.
07:55According to Page Six, Vanessa's father, Charles Hayden, had invested in several stocks and
07:59assets that eventually matured following his death in 2005.
08:02As a source claimed,
08:03I can't speculate as to how much they received, but it was life-changing.
08:07The amount was reportedly enough for Vanessa's mother, Bonnie Hayden, to pay $6.5 million
08:12in cash for a lavish penthouse in New York City.
08:14And it may have also been the straw that broke the camel's back of Vanessa's strained marriage.
08:19But money was far from the only issue, as Don Jr.'s alleged infidelity was also a problem
08:23throughout their relationship.
08:24As the source noted,
08:25There have been numerous affairs.
08:27This divorce has been in the works for a long time.
08:30Vanessa Trump made headlines in 2021 when it was reported that she was in a romantic
08:34relationship with a Secret Service agent during her former father-in-law's presidency.
08:38According to Washington Post reporter Carol Lennig's book, Zero Fail, The Rise and Fall
08:43of the Secret Service, Vanessa and her former sister-in-law, Tiffany Trump, reportedly became
08:47close to the agents who protected them, to an inappropriate degree.
08:50Lennig didn't specify if Vanessa began dating the agent before or after she filed for divorce,
08:55although that didn't stop tabloid speculation that she may have been having an affair.
08:59Vanessa's representatives didn't comment on the controversy, although Tiffany's reps released
09:03a statement to The Washington Post that read,
09:05Tiffany's experience with the Secret Service was entirely professional.