2 – Linda McMahon
Sixteen years before Donald Trump became famous on The Apprentice, he made his entertainment debut at WWE’s WrestleMania IV. In 1988, Linda and Vince McMahon, the pro wrestling power couple, hosted their event at Trump Plaza in Atlantic City. Trump won the “Battle of the Billionaires” there and even shaved Vince’s head in the ring.
Since then, Linda McMahon has remained one of Trump’s closest female friends. The McMahons donated $5 million to the Trump Foundation between 2007 and 2009. Additionally, Linda personally contributed $6 million to Trump’s presidential campaign. She once said, “Once he’s your friend, he is loyal to the end.” This loyalty likely influenced President Trump’s decision to appoint her as head of the Small Business Administration.