When battle-hardened Trump funded Kamala Harris's election campaign

Donald Trump, now a right-wing Republican, switched sides regularly. He was once a registered Democrat and had a soft corner for the party he now bashes. Trump also funded the campaigns of Kamala Harris, twice. The same Harris he would go on to defeat in the 2024 presidential election.

"I was looking at the ones I'm running against. I've contributed to most of them. Can you believe it? I contribute to everybody. I've given to Democrats. I've given to Hillary (Clinton). I've given to everybody because that was my job," Donald Trump said of the political donations he made during his presidential campaign in 2016. Trump's mention of Hillary Clinton was interesting because it was Hillary, the Democratic Party candidate, who was contesting against him. But it wasn't just Hillary Clinton, Trump, now a hardcore Republican, also funded the political campaigns of Kamala Harris, who he defeated in the 2024 presidential election.

Before stepping into politics, Trump was a crafty businessman, and, believe it or not, he was even a member of the Democratic Party.

Trump funded Kamala Harris's campaign to be California's Attorney General not once, but twice. Even though Trump was a Democratic Party member from 2001 to 2009 and cosied up with Democrats, he contributed to the campaigns of Kamala Harris as a hardcore Republican, a party which he first joined in 1987, campaign records reveal.

And not just Donald Trump, his daughter Ivanka too contributed to Kamala Harris's campaign.

But why was Trump keen to finance Harris, a Democrat, and his later-to-be future rival for the White House, when the now Vice President was just beginning to build her attorney career in Californian politics?

DONATIONS TO KAMALA HARRIS'S CALIFORNIA ATTORNEY GENERAL CAMPAIGNS

The donation saga goes back to September 2011, a year after Kamala Harris was first sworn-in as the Attorney General of California.

At that time, Trump, a successful real-estate developer, was not associated with any party, and contributed $5,000 to Harris's campaign fund. This donation was made as Harris was laying the groundwork for her re-election bid in 2014.

A cheque of $5,000 dated '26 September 2011', with Trump's signature and made payable to 're-elect Attorney General Kamala D Harris 2014' went viral on social media. Jared Moskowitz, a Democratic lawmaker from Florida, posted a photo of the cheque on Twitter (now X) and wrote, "Wise investment".

“When Trump wrote that check to re-elect Kamala Harris in 2011, I bet he didn’t think she’d cash it in 2024,” snarked Michael Steele, former chair of the Republican National Committee, according to a Guardian report.

Two years later, in 2013, Trump, now a Republican, again backed Kamala Harris's re-election campaign by donating an additional $1,000, a year before she won a second term, according to campaign finance records. Harris unexpectedly received further support for her re-election bid as Attorney General when Trump's daughter, Ivanka, donated $2,000 to her campaign in 2014.

So why did Trump make donations to Kamala Harris?

The reason could be attributed to Trump's broader strategy as a businessman to build relationships and long-lasting influence across the American political spectrum.

Steven Cheung, a Trump campaign spokesperson, in July 2024 dismissed the donations as made by a "global businessman" to "corrupt politicians", according a New York Times report.

“President Trump was a global businessman and knew how to play the game and win the game with corrupt politicians like Kamala Harris. Now he’s going to finish the job of throwing all these crooked politicians out of office,” Cheung said.

Despite receiving these funds from Trump and his daughter, Kamala Harris chose not to retain the money from Trump's donations.

After her successful re-election as Attorney General, Harris, in 2015, redirected the $6,000 she received from Trump to a non-profit organisation that advocates for civil and human rights for Central Americans, according to Harris's campaign.

She made this tactical move when she was launching her campaign for the US Senate, where she was elected from 2017 to 2021.

DONATIONS WHEN TRUMP UNIVERSITY WAS UNDER PROBE

The donations by Trump to the Harris campaign also came at a time when he was facing a class-action lawsuit into whether Trump University bilked students, according to a New York Times report in July.

"Harris’s office never took action against the entity; officials working for Harris said at the time the donations had nothing to do with that lack of action," it reported.

The NYT approached Harris's officials, who did not respond to requests for comment on the funding issue and the probe.

TRUMP'S DONATIONS TO TOP DEMOCRATS

Not just to Kamala Harris, Donald Trump made big-buck donations to politicians from both the Republican and Democratic camps before his entry into politics. As per records, he gave money to prominent Democrats, including California Governor Gavin Newsom and then-Senators Joe Biden and Hillary Clinton, as well as top Republicans, including Senator Mitch McConnell and Texas Governor Greg Abbott.

According to Ballotpedia, the digital encyclopedia of American politics, Trump made $1,845,290 in political donations between 1989 and 2015. A majority of them were for the Republicans, although Trump was generous enough to donate more money to the Democrats before 2011, incidentally, when he himself was a Democrat.

TRUMP WAS A REGISTERED DEMOCRAT

Trump became a Republican when he joined the party in 1987. But records show that he jumped ships five times before settling down with the GOP finally in 2012.

In 1999, Trump left the Republican Party and joined the Independence Party of New York, a state affiliate of the Reform Party USA. Incidentally, Trump declared himself a potential candidate for the Reform Party's presidential nomination for the 2000 election. But he decided to quit the race after just four months.

In 2001, Trump made a pivotal decision to join the Democrats, a party which he now bashes over a range of contentious issues like the economy, immigration and border security.

Despite Harris refusing to retain his donations for her California Attorney General campaigns, Trump had a soft corner for Democrats, a marked contrast from his usual rhetoric and hardline image. In an interview with CNN in 2004, Trump said he identified himself more as a Democrat than a Republican "in many cases".

"It just seems that the economy does better under the Democrats than the Republicans. It shouldn't be that way. But if you go back, I mean it just seems that the economy does better under the Democrats. Certainly, we had some very good economies under Democrats, as well as Republicans. But we've had some pretty bad disaster under the Republicans," he had said.

Going back a little further, Trump told the Playboy magazine in 1990 that he would do better as a Democrat than a Republican if he ever ran for office.

"Well, if I ever ran for office, I'd do better as a Democrat than as a Republican. And that's not because I'd be more liberal, because I'm conservative," he said.

But fast-forward to 2016, 2020 and 2024, Trump ran for the White House thrice, and as a Republican.

The result -- Trump defeated Hillary Clinton in 2016 but lost to Joe Biden in 2020. Four years later, he made a grand comeback to the Oval Office following a tumultuous period where he refused to accept his 2020 loss, survived two assassination attempts and faced a mountain of legal challenges, including being convicted for felony crimes.

FLIP-FLOPS AND RETURN AS REPUBLICAN

Even after heaping praise on the Democrats, Trump left the party in 2009 and changed his affiliation back to the Republican Party. But two years later, Trump flipped again, changing to "no party affiliation" (independent). Again in 2012, Trump returned to the Republican Party and has not abandoned it since then.

Today, Trump is the leader of the Republican Party, having won the 2016 presidential race and now, defeating Harris, whom he financially backed twice while she was making a mark in politics.

Trump acknowledged his history of making donations to top Democrats and defended them at a rally during his 2016 campaign trail. "I've got to give to them, because when I want something, I get it. When I call, they kiss my a**."

As his 2024 campaign spokesperson Steven Cheung said, Trump was a "global businessman" and knew "how to play and win the game".

For Trump, it was just business. If he won 2016 due to his famous "Make America Great Again" and demonising the Democrats over economy, immigration and trade, 2024 was about him portraying himself as a "victim of a political conspiracy" due to his legal troubles. He punched above his weight and stormed into the White House again, becoming the first president in 132 years to win non-consecutive terms. That wasn't business as usual.