During his 2016 presidential campaign, Donald Trump acknowledged his history of contributing to candidates across the political spectrum. “I contribute to everybody… I’ve given to Democrats. I’ve given to Hillary,” Trump remarked, highlighting his support for the then-Democratic candidate he was running against. Beyond Hillary Clinton, Trump, now a staunch Republican, also donated to Kamala Harris, whom he defeated in the 2024 presidential race.
Before his foray into politics, Trump was a shrewd businessman—and even a registered Democrat from 2001 to 2009. Surprisingly, he financially supported Kamala Harris’s campaigns for California Attorney General not once, but twice. Despite being a registered Republican at various times since 1987, Trump crossed party lines to contribute to Harris’s campaigns, with records showing donations of $5,000 in 2011 and $1,000 in 2013. His daughter, Ivanka Trump, also contributed $2,000 to Harris’s 2014 re-election.
Why would Trump back a future Democratic rival? The answer seems rooted in his strategy as a businessman to maintain influence across political affiliations. His campaign spokesperson, Steven Cheung, later dismissed these donations, saying Trump was a “global businessman” who navigated political circles strategically. “President Trump knew how to play the game and win it with corrupt politicians,” Cheung stated in July 2024.
Kamala Harris, however, did not retain Trump’s donations. Instead, after her re-election as Attorney General, she redirected the $6,000 she received to a non-profit that supports civil rights for Central Americans, particularly as she began her Senate campaign.
The Timing of Trump’s Donations
Trump’s financial support for Harris coincided with scrutiny around Trump University, which was under investigation. Although Harris’s office did not pursue the case, her staff asserted that campaign donations did not influence this decision.
Trump’s History of Donations to Democrats
Trump’s contributions went beyond Harris, extending to other Democrats like Gavin Newsom, Joe Biden, and Hillary Clinton. According to Ballotpedia, between 1989 and 2015, Trump donated $1.8 million in political contributions, with a majority going to Republicans. Still, prior to 2011, he gave more to Democrats during a period when he identified as one.
From Democrat to Republican Leader
Despite this past alignment with Democrats, Trump changed his affiliation five times before firmly aligning with the GOP in 2012. In 1999, he joined the Independence Party but soon left, later joining the Democrats in 2001. In a 2004 interview, he shared, “The economy does better under Democrats.” By 2012, however, Trump returned to the Republicans, becoming the party’s leader and presidential nominee.
Trump’s Perspective: “Just Business”
Reflecting on his donations in 2016, Trump explained he gave strategically: “When I want something, I get it. When I call, they kiss my a**.” His recent spokesperson reiterated this, calling him a “global businessman” who played the political “game.”
After losing to Biden in 2020, Trump’s return to the White House in 2024 broke a 132-year record, as he became the first president since Grover Cleveland to serve non-consecutive terms. For Trump, it was no longer business as usual; it was the culmination of a political comeback defined by resilience and strategic alliances across the aisle.