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10. Brooklyn Businessman
Donald Trump desperately wanted to build upon his father’s success. Even after being named the president of E. Trump & Son, Donald Trump was constantly seeking praise and validation from his biggest business mentor, Fred Trump. While sharing the above photo on Facebook, Trump wrote “#TBT With my father, Fred Trump, in Brooklyn, 1975. A great Father’s Day gift – a stay at my 5 star hotel”. While becoming Fred’s mentee, Trump had successfully started, financed, and expanded his own commercial real estate projects. Although Fred Trump rarely discussed personal matters in public, there is little doubt he was proud of his fourth child’s success early on.