Celebs Who Secretly Donated to Both Sides of the Aisle

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While Hollywood is often seen as strongly leaning left politically, campaign finance records show a more complex picture. Many celebrities quietly donate to candidates from both major parties – Democrats and Republicans – to build influence or support friends, even if it clashes with their public image or stated beliefs. A look at Federal Election Commission data confirms that numerous well-known figures have funded candidates across the political spectrum.

Donald Trump

Before becoming a politician, the former President frequently donated to both Democrats and Republicans. Records show he gave thousands of dollars to Kamala Harris when she was California’s Attorney General in 2011 and 2013. He also significantly supported the Clinton Foundation and Hillary Clinton’s Senate campaigns while a registered Democrat in New York. Before securing the Republican nomination in 2016, he contributed to other prominent Democrats like Chuck Schumer and Joe Biden. During debates, he justified these past donations by saying that, as a businessman, maintaining good relationships with people in power was essential.

Elon Musk

Over the past ten years, the tech leader has noticeably changed his political leanings. He used to consider himself a moderate and financially supported Barack Obama’s 2012 reelection campaign with a donation exceeding $100,000. He also contributed to Hillary Clinton’s 2016 presidential campaign and voiced reservations about her opponent. More recently, however, his spending has shifted significantly toward the Republican party, with large donations to groups supporting Donald Trump in the 2024 election. This change—from supporting established Democrats to heavily funding the more populist wing of the GOP—shows a clear shift in his political beliefs.

Robert Kraft

Robert Kraft, the owner of the New England Patriots, has a complicated relationship with politics. While he’s a long-time Democrat and generously supported Barack Obama’s presidential campaigns, he’s also built a relationship with Donald Trump, even gifting him a Super Bowl ring and donating a million dollars to Trump’s inauguration. It seems Kraft prioritizes personal connections and what’s good for his business over strict political party lines. This approach lets him maintain relationships with both sides, which is helpful as the owner of a professional sports team in a politically sensitive world.

Mark Cuban

Mark Cuban, the billionaire businessman and former ‘Shark Tank’ star, doesn’t fit neatly into either political party. While records show he donated to Republican Senator Orrin Hatch in 1996, he later supported Democratic candidates like Zoe Lofgren, and publicly backed Hillary Clinton and Joe Biden. Cuban says he decides who to support based on each candidate’s merits, not party lines. This makes his early donation to a conservative senator surprising, given his recent outspoken support for Democrats.

Kanye West

The rapper, known for making surprising statements, also has an unpredictable history of political donations. In 2015, he donated $2,700 to Hillary Clinton’s campaign, but then became a vocal supporter of Donald Trump. He even visited the White House wearing a ‘Make America Great Again’ hat and publicly praised the Republican president. This earlier support for Clinton surprised many, and his later, unsuccessful run for president only added to the confusion surrounding his political views.

Frank Sinatra

Frank Sinatra offers a classic example of how celebrities can change their political views and fundraising efforts over time. He started as a strong supporter of Franklin D. Roosevelt and worked hard to get John F. Kennedy elected in 1960. Later, he grew distant from the Democratic party and officially became a Republican in the 1970s. He developed a close friendship with Ronald Reagan, donating to his campaigns and even planning his 1981 inaugural gala. Sinatra’s shift from a major Democratic fundraiser to a Republican figure shows how personal connections can significantly influence someone’s political beliefs throughout their life.

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2025-12-19 02:44