From Business Mogul to President: Vintage Photos of Donald Trump's Rise To Power

By Jack Ripley | April 29, 2024

The King of Pop and The Donald

Welcome to a captivating journey through time with vintage photos of the 45th President of the United States, Donald J. Trump. Whether you're a devoted fan or just curious about his early days, this slideshow offers a glimpse into the life of one of the most iconic and polarizing figures in modern American history. From his days as a young real estate maverick in New York City to his early forays into the world of business and celebrity, these images tell a story of ambition, determination, and the makings of a future leader. Join us in exploring the moments and places that shaped the man who would later occupy the highest office in the land. So, let's dive into the past and continue this remarkable journey through vintage snapshots of Donald Trump's life.

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Getty Images

The unlikely friendship between Donald Trump and Michael Jackson was a captivating example of two larger-than-life personalities bonding over their shared fame, wealth, and extravagant lifestyles. Throughout the 1980s and '90s, they moved in similar circles, attending fashionable fundraisers and high-profile events together. Both men were known for their lavish tendencies, from gold toilets to private amusement parks, which likely contributed to their connection. Despite their rapidly diverging paths in the 2000s, with Jackson facing controversies and legal challenges while Trump entered the world of politics, Trump continued to publicly support Jackson. Even in the lead-up to the 2016 election, he described the late King of Pop as "misunderstood," showcasing the enduring nature of their friendship and Trump's loyalty to his celebrity associates, even when they faced significant challenges in their public lives.

The Donald Helps Kevin McCallister in Home Alone 2

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Alamy

Donald Trump made a brief yet memorable cameo appearance in the 1992 holiday classic film "Home Alone 2: Lost in New York." In the movie, a young Kevin McCallister, played by Macaulay Culkin, finds himself lost in the vast corridors of the Plaza Hotel in New York City. When Kevin approaches the hotel's front desk, he encounters Donald Trump, who happens to be the owner of the Plaza at the time. Trump kindly provides Kevin with directions, and his appearance in the film was seen as a fun and unexpected moment that added a touch of celebrity to the movie. Over the years, this cameo has remained a lighthearted and nostalgic aspect of both Trump's public image and the film itself.