The Most Surprising Trump Family Celebrity Friendships

Donald Trump, the 47th president-elect of the United States, is a polarizing figure in modern American history. His presidency, campaign rhetoric, and post-presidency controversies have deepened political divides, with experts agreeing that the current political climate is one of the most fractured in decades. The tribalism that has taken hold in American society along with this division has led to public disputes, severed relationships, and even conflict among friends and families. 

In such a sensitive climate, it may seem surprising that members of the Trump family have managed to maintain friendships with high-profile figures from liberal Hollywood and beyond. The divide between Donald Trump's politics and the overwhelmingly progressive entertainment industry only adds to the intrigue surrounding these relationships. From Hollywood A-listers to family members of political rivals, these bonds challenge the more modern cultural expectation that political differences must necessarily lead to personal estrangement.

Hugh Jackman, known for his roles in blockbuster films such as "X-Men" and "The Greatest Showman," has a surprisingly close connection to Ivanka Trump and her husband, Jared Kushner. The friendship predates Donald Trump's presidency, with Jackman himself explaining the depth of their bond. "I've known those guys for 15 years," Jackman told Variety in 2018. The actor went on to explain how they manage to dodge discussing politics at personal functions. "We don't talk politics at birthday parties," he said. His remarks were a direct response to the media scrutiny of his relationship with the prominent Trump-Kushner couple, given their controversial role in politics during Donald Trump's first presidency. 

During an appearance on "The View" in 2018, Jackman addressed the criticism further. "They've always been so kind and generous," he said, per ABC News. "People question, 'Really?' And I'm kinda like, 'OK, let's say your friends of 15 years' father became president. Whether you agree with the politics or not, do you just dump your friends?'" The actor said he doesn't understand people who do that. 

This perspective highlights the challenging balance many people have to strike between personal relationships and political values during a highly polarized time in American history. Jackman and his wife, Deborra-Lee Furness, were also seen mingling with Ivanka and Jared at social events in New York long before the Trump political era began. This enduring connection demonstrates how personal bonds can transcend the divisive nature of modern politics, even when public opinion complicates these friendships.

One of the most unexpected connections in the world of politics is the friendship between Tiffany Trump and Naomi Biden. Both women come from two of the most prominent clans in American politics, and their relationship stands out as a rare example of personal connection overcoming family rivalry. Tiffany Trump, Donald Trump's daughter, and Naomi Biden, Joe Biden's granddaughter, both attended the University of Pennsylvania, where they graduated in 2016. Their shared educational background appears to have been the foundation for their unlikely friendship. This connection came to public attention in 2018 when Tiffany, a former party girl, posted a photo on Instagram of herself with Naomi during a weekend in the Hamptons. 

The post surprised many, given the stark political divide between their families. While neither Tiffany Trump nor Naomi Biden publicly commented on their friendship in detail, their visible camaraderie hints at a personal relationship untouched by political tension. The friendship is particularly striking given the intense animosity between their fathers during the 2020 presidential election. Despite this, the two seem to have managed to maintain their relationship. Are politics just their parents' problems? 

NFL superstar Tom Brady's friendship with Donald Trump dates back decades, long before the real estate mogul entered the political arena. The two first connected in the early 2000s. In 2015, Brady confirmed their friendship during an interview. "He's a good friend of mine," he said on WEEI radio station in December of that year (via NBC Sports). "He's always been so supportive of me." The relationship gained attention during Trump's 2016 presidential campaign, particularly when a "Make America Great Again" hat was spotted in Brady's locker. While Brady insisted he was not endorsing Trump politically, he admitted to WEEI in September 2015 that it's a "nice keepsake," as CBS News reported.

In other interviews, Brady was more cautious about discussing politics. "I'm just here to play football," he said at a press conference in December the same year (via CBS News). Regardless, the public perception of their friendship has endured, with Trump frequently referencing Brady during rallies. As reported by CBS News, Trump referred to Brady as "the greatest quarterback of all time" as recently as 2019. Despite their seemingly strong bond, there have been signs of distance in recent years. Notably, Brady opted not to attend White House visits during Trump's presidency. The NFLer's relationship with Trump highlights the complexities of personal connections in a polarized political landscape.

Once a symbol of bipartisan camaraderie, the friendship between Chelsea Clinton and Ivanka Trump has taken a significant turn over the years. In early 2016, Chelsea spoke openly about their bond, telling People, "Friendship is always more important than politics." Their relationship seemed to reflect their shared experiences as daughters of two of the most influential political figures in modern American history. However, the 2016 presidential campaign introduced a strain that proved too difficult to overcome. The intense rivalry between Hillary Clinton and President-elect Donald Trump brought public scrutiny to their friendship, with many questioning whether it could endure. 

By 2022, Chelsea gave skeptics an answer in an interview on "Watch What Happens Live." "We were definitely friends," she told show host Andy Cohen. Chelsea continued to explain that Ivanka had shifted from the person she knew in her early years. "She went to the dark side," she declared. According to Chelsea, the last time she spoke to Ivanka was just after the 2016 election.

Chelsea's statements reflect the broader challenges faced by personal relationships in an era of political polarization. For her, Ivanka's active role in her father's administration — along with her public alignment with his policies — seemed to cross a line. The falling out between the pair is emblematic of how politics can impact even the most personal of bonds and underscores the difficulty of maintaining friendships across deep ideological divides, particularly when the stakes are as high as they are in contemporary American politics.