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 couple years since Pritzker, the world’s only known trans billionaire and a Republican mega-donor, 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.
The donors have a mixed record of prior support for Republicans. Some, like Pritzker, consistently contributed large sums to GOP candidates. Others had more bipartisan giving histories. And some chipped into the Trump inaugural despite largely supporting Democrats in the past.
Taken together, though, the crop of donors who ponied up to celebrate Trump’s 2016 victory only to actively combat his re-election a few years later represent some notable political defections. And while the Trump re-election effort certainly is not hurting for cash as the election year begins, those defections signal some discontent among donors who, undoubtedly for various reasons, chose to signal their support for the new president just a few years ago.
Pritzker, a retired U.S. Army lieutenant colonel, is by far the biggest name on the list, and her donation to Buttigieg came in the wake of a Washington Post column detailing her drift away from the party with which she’d long associated.
“I’ve grown frustrated as I watch this Republican administration push to ban transgender military service. Anti-transgender platforms are causing me to evaluate my party support,” Pritzker wrote. “I have hoped the Republican Party would reform from within and end its assault on the LGBTQ community. Yet, the party continues to champion policies that marginalize me out of existence, define me as an eccentric character and persecute me for using the public restrooms that correspond to my gender identity.”
In 2016, Pritzker donated to Trump and a number of his Republican primary rivals, including Ben Carson, Marco Rubio, Jeb Bush, and John Kasich. Her office did not respond to inquiries about her support for Buttigieg, the first openly gay person to run a viable presidential campaign for a major political party.
Greg Maffei, the chief executive of the Colorado-based media company Liberty Media, is another $250,000 donor to the Trump inaugural who is backing Democrats in 2020. Though he didn’t donate to Trump’s presidential campaign, he did so for Mitt Romney in 2012 and John McCain in 2008.
This time around, though, Maffei has supported the two Democratic presidential candidates from his home state. In March 2019, he gave the per-election maximum of $2,800 to Hickenlooper, the former Colorado governor. Two months later, after a max-out donation to Republican Sen. Cory Gardner, Maffei donated $100,000 to a super PAC supporting Hickenlooper. After Hickenlooper withdrew from the race, Maffei donated the legal maximum to Bennet’s presidential campaign.
Like Maffei, Virginia electrical contractor William Dean had donated to Romney and McCain, as well as George W. Bush’s presidential campaign in 2000. He declined to make any contributions to 2016 presidential candidates, but chipped in $100,000 for Trump’s inauguration.
In 2020, though, it appears Dean is supporting Gabbard’s presidential bid. His donation to the Hawaii congresswoman’s campaign was small—just $500—but it marks the first time he’s contributed to a Democratic candidate for the White House.
Chrysa Tsakopoulos Demos, the chief executive of California land development company AKT Investments, is a longtime Republican donor who backed Sen. Ted Cruz’s bid for the 2016 Republican presidential nomination. She donated $5,000 to the Trump inaugural, and continued donating to Republicans through 2018, including House Minority Leader Kevin McCarthy, the National Republican Congressional Committee, and Great America Committee, Vice President Mike Pence’s political group.
But Demos’ only federal political contribution so far in the 2020 cycle is the $2,800 she donated last year to Biden’s presidential campaign.
Presidential inauguration committees are unique among political groups in that they collect money for political candidates who have already won their elections. That means that motivations for donating are often different than for traditional political groups seeking to actually elect candidates. Though donors often give to campaigns and super PACs in the hope of currying favor with officeholders, such conduct is amplified by financial solicitations for entities affiliated with officials who have already prevailed in their elections and are simply waiting to be sworn in.
As a result, it’s more common to see donors cross the political aisle to donate to an inauguration committee. And while Republicans who supported Trump during the campaign put up huge sums to support his inauguration, even some who are now backing Democrats seeking to unseat him, Trump’s inaugural also took in money from Democrats and people who supported Hillary Clinton’s 2016 campaign. A number of those donors have now reverted to their Democratic support in 2020.
Leonard Wilf, a real estate developer and co-owner of the Minnesota Vikings, has donated to both Democrats and Republicans. But just a few weeks before the 2016 election, he donated $2,700 to Clinton’s campaign and another $5,000 to a PAC supporting her. When Clinton lost, Wilf chipped in $25,000 to Trump’s inaugural committee. With Trump back on the ballot, though, Wilf is once again supporting a Democrat; in March 2019, he maxed out to Klobuchar’s campaign.
Florida physician Azzam Muftah maxed out to Clinton’s campaign in 2016 and wrote a handful of checks to the Democratic National Committee. But he donated $3,000 to the Trump inauguration, and during the 2018 cycle donated to a number of Senate Republicans, including Tom Cotton, Lindsey Graham, Mike Braun, and Jim Risch.
Come 2019, though, Muftah began chipping in to Trump challengers. So far this cycle, he’s donated to both Buttigieg and Booker.
Bruce Mosler, the chairman of real estate giant Kushman & Wakefield’s global brokerage practice and a $25,000 donor to the Trump inaugural, really likes to hedge his bets. During the 2008 presidential race, he donated to the campaigns of Clinton, Biden, and Rudy Giuliani. In 2012, he supported both Romney and Barack Obama. Four years later, he donated to both Clinton and Trump.
In 2020, though, Mosler is supporting Biden. He’s donated $5,000 to Biden’s PAC and another $2,800 to his campaign.
For Indiana physician Hytham Rifai, who gave $2,500 to Trump’s inauguration, the hedging has continued this cycle as well. Rifai supported both Clinton and Bush during the 2016 cycle. In March 2019, he donated to Trump again, and to a joint fundraising committee supporting the president’s reelection.
A month later, Rifai chipped in to Booker’s presidential campaign as well.
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