They Donated to Trump's Inauguration. Now These Big Donors Are Funding His 2020 Competition

In January 2019, Jennifer Pritzker wrote an impassioned plea to her political party: She was a lifelong Republican, but the GOP was driving her away with messaging and policies targeting transgender people.

It had only been a few years since Pritzker, the world’s only known trans billionaire and a Republican megadonor, had chipped in a whopping $250,000 to President Donald Trump’s inaugural committee. But three months after publicly objecting to the GOP’s stance on trans issues, she gave $1,000 to Democrat Pete Buttigieg’s presidential campaign.

Pritzker is a member of a prominent, wealthy, and politically active family (her cousin J.B. Pritzker is the Democratic governor of Illinois, and his sister Penny was Barack Obama’s commerce secretary). But she is far from the only donor to Trump’s inauguration who has financially supported one of his potential Democratic presidential challengers.

The Daily Beast tallied 15 such donors who collectively gave more than $700,000 to Trump’s inaugural committee but who have since contributed to the presidential campaigns of Democratic candidates, including Buttigieg, Joe Biden, Elizabeth Warren, Cory Booker, Tulsi Gabbard, Amy Klobuchar, Michael Bennet, John Hickenlooper, Eric Swalwell, and John Delaney.