This episode takes a look at the Trump family through the lens of Tiffany Trump, the often-overlooked daughter from Donald Trump’s marriage to Marla Maples.
We explore how the three eldest Trump children—Don Jr., Eric, and Ivanka—have evolved into what the author describes as shallow, morally compromised figures who actively embrace the spotlight. Don Jr.’s transformation from rebellious teenager to a “crasser” version of his father, Eric’s tragic physical and mental decline, and Ivanka’s failed attempt to escape the family’s reputation are all examined.
The focus then shifts to Tiffany, who grew up largely in California with her mother, away from the family’s New York operations. Despite appearing to be the “different” Trump child—pursuing law school and maintaining a lower profile—recent revelations suggest she couldn’t escape the family pattern.
The bombshell: Tiffany’s husband, Michael Boulos, initially portrayed as a billionaire heir, allegedly attempted to defraud her brother-in-law Jared Kushner out of millions in a yacht deal. The scheme involved misrepresenting costs and pocketing an extra $3.5 million in commission. Meanwhile, investigations revealed the Boulos family wealth was largely fabricated—Michael’s father works as a machinery salesman for a penny-stock Nigerian company.
The episode concludes that Tiffany, despite her attempts at respectability and distance from the family, ultimately chose a partner who operates straight from the Trump playbook, proving that even the most promising Trump offspring couldn’t escape the family’s transactional, morally dubious legacy
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