President Trump, who spent decades changing his party registration and supporting candidates of different ideological stripes, has never made a secret of his various donations to Democrats over the years.
So it perhaps shouldn't come as a surprise that Mr. Trump and members of his immediate family have given money in the past to several of the Democrats running to unseat him in 2020.
The Democratic presidential primary field is already the largest in modern history, with nearly two-dozen candidates having announced campaigns. Here are the Democratic presidential hopefuls who Mr. Trump and his children have given money to over the years.
Former Vice President Joe Biden
Federal filings show Mr. Trump made a $1,000 donation to Biden through the Citizens for Biden committee back in 2001. At the time, Biden was running for his sixth term in the Senate representing Delaware.
On April 25th, Biden joined the crowded Democratic presidential primary field, announcing his run. Biden's campaign did not response do request for comment about the donation.
California Sen. Kamala Harris
In 2011, the year Harris became California's attorney general, Mr. Trump donated $5,000 to her. Two years later, in 2013, he donated another $1,000 to her re-election effort.
According to Harris's presidential campaign, Mr. Trump's contributions were later donated to a non-profit focused on human and civil rights advocacy for Central Americans in 2015.
Ivanka Trump, the president's daughter and senior adviser, also donated $2,000 to Harris's re-election as attorney general in 2014.
New York Sen. Kirsten Gillibrand
In 2010, Mr. Trump donated a total of $4,800 to Gillibrand over the course of two separate donations. In 2007, when Gillibrand was still in the House, Mr. Trump chipped in a little more than $1,000 toward her re-election effort.
Ivanka Trump also gave to Gillibrand in 2014 after she won her first full term in the Senate.
New Jersey Sen. Cory Booker
Ivanka Trump and her husband Jared Kushner, who also works as a senior adviser to Mr. Trump, both donated to Booker. According to FEC filings, the couple gave $5,200 to the then-Mayor of Newark for both the primary and general Senate special election in 2013.
Kushner and Ivanka Trump also donated $10,000 to the Booker Senate Victory joint fundraising committee the following year.
What the Trump campaign says about the donations
"This question has been asked and answered by President Trump many times," said a Trump campaign official when asked for comment on the donations. "As a businessman, it was par for the course to donate to elected officials in both parties."
Mr. Trump's campaign donations to Democrats over the years, including Hillary Clinton, were a minor issue when he ran for the Republican nomination. Mr. Trump was able to quickly defuse the issue, however, by saying he was just doing what was necessary to survive in a "broken system."
"I give to everybody. When they call, I give," Mr. Trump said on the debate stage in 2015. "And you know what? When I need something from them, two years later, three years later, I call them. They are there for me. That's a broken system."
But that hasn't stopped Mr. Trump from using his donations as a cudgel against his Democratic opponents. After Gillibrand called for him to resign from office in 2017, for example, Mr. Trump tweeted that she used to.
Outside of Mr. Trump's immediate family, Joshua Kushner, who is Ivanka Trump's brother-in-law, has contributed numerous times to Democrats who are now running for president.
In 2018, Joshua Kushner gave $2,600 to then-Rep. Beto O'Rourke's Texas Senate campaign. In 2013, he also donated to Rep. Seth Moulton's campaign.
O'Rourke launched his presidential campaign in March. Moulton announced his bid in April.
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