For the three Republican primary challengers seeking to unseat President Donald Trump in 2020, the future ahead may be grim.
The Republican National Committee has pledged “undivided support” for Trump’s re-election bid, and the candidates cannot compete against the president’s record-breaking cash reserve. Trump entered the final quarter of 2019 with $83 million on hand, compared to a combined $1.7 million total for his primary opponents.
But the candidates are getting support from some unlikely allies. More than two dozen donors who maxed out to one or more of the three candidates have a recent history of giving to Democrats, an OpenSecrets analysis found. Some of Trump’s most outspoken conservative critics, as well as donors to Trump’s 2016 primary opponents, are also aiding the Republicans seeking to upset the president’s re-election bid.
Unlike the fierce horse race in a crowded Democratic field, Republican challengers’ voices are largely diminished by Trump’s unwavering base and a powerful fundraising machine backed by his own party. Lacking momentum, all are struggling to build up serious campaign efforts to battle the incumbent.
Former Massachusetts Gov. Bill Weld, the first Republican to challenge Trump in 2020, has raised $1.3 million since his announcement in April, including personal loans totaling $180,800. Some of his campaign’s biggest donors, however, are also betting on Democratic frontrunners to bid against the president.
Ted Dintersmith, a Massachusetts education philanthropist, gave $2,800 to Weld’s campaign, hitting the contribution limit for the primary under the law. But the businessman also maxed out to two Democratic presidential hopefuls at the same time: entrepreneur Andrew Yang and South Bend Mayor Pete Buttigieg. In April, Dintersmith promoted a Boston-area breakfast fundraiser with Buttigieg on his LinkedIn page.
Jonathan Davis, a Boston-area real estate executive, maxed out to Weld’s campaign as well. Like Dintersmith, Davis is also investing in several Democratic contenders, giving $2,800 to former vice president Joe Biden and $1,000 each to Sens. Amy Klobuchar (D-Minn.), Cory Booker (D-N.J.) and Kamala Harris (D-Calif.).
Weld also garnered max contributions from documentary filmmaker Susan Rockefeller and her husband, David Rockefeller Jr., who maxed out to then-presidential candidate Hillary Clinton in 2016. He also gave $2,000 to Booker’s campaign and $1,000 to Washington Gov. Jay Inslee, who dropped out of the race in August.
Apart from the Rockefellers, other former Clinton donors are also giving to Republican presidential candidates this cycle. Ann Gund, wife of architect Graham Gund, maxed out to Weld’s campaign. She gave $2,700 to Clinton in 2015, and gave former president Barack Obama $4,600 in 2008.
Former Rep. Joe Walsh (R-Ill.), who launched his primary challenge against Trump in late August, also received several maximum contributions from Democratic donors. The Illinois Republican has raised $234,746, including a personal loan of $100,000 to kickstart the campaign.
Thomas Barron, a Colorado-based author, donated $2,800 to Walsh’s campaign. He gave Democratic Party committees $135,500 to aid candidates in congressional races this year. Barron also gave $5,000 each to Booker and presidential contender Sen. Michael Bennet (D-Colo.).
Also maxing out to Walsh is Steven Markoff, CEO of a Santa Monica-based financial services firm. Markoff gave Harris $2,700 this cycle and gave $2,800 to Rep. Adam Schiff (D-Calif.), who chairs the House Intelligence Committee handling the impeachment probe into the president over the recent Trump-Ukraine controversy.
Democratic donors are not alone in investing in the triangle of Republican primary challengers to weaken Trump’s foothold. Outspoken Trump critics, along with some who supported Trump’s primary challengers in 2016, are now giving to the GOP contenders to upset Trump’s re-election.
George Conway, husband of Trump adviser Kellyanne Conway, gave Walsh’s campaign $5,600. In 2016, Conway gave $5,275 to Trump’s campaign and $22,300 to the Republican National Committee. The New-Jersey based attorney also made multiple contributions to Trump’s primary opponent Ted Cruz, almost all of which were returned to him.
After the inauguration, the former Trump supporter flipped. Conway rejected a potential job at the Justice Department in 2017 and then grew vocal on Twitter, publicly criticizing the president’s allies and his political decisions. In an Atlantic op-ed titled “Unfit for Office,” he questioned the president’s mental stability, calling him “volatile and erratic” and “incapable of consistently telling the truth.”
Another vocal Trump critic, Bill Kristol, gave $1,000 each to Walsh, Weld and former South Carolina Gov. Mark Sanford, who has raised a little more than $60,000. Kristol, director of the conservative advocacy group Defending Democracy Together, has long been working to replace Trump with another Republican candidate. The group backed a $1 million TV and digital ad campaign in September, accusing Trump of abusing his presidential power and asking Republicans to hold him accountable.
The “Never Trumper” talked to former White House communications director Anthony Scaramucci in August, seeking competent candidates to put on the GOP ticket. In a recent New York Times op-ed, Kristol called for Republicans to run against the president. “Win or lose, you will go down in the history books as a man or woman of honor,” he wrote.
Andy Zwick, who sits on the board of the Foundation of Constitutional Government with Kristol, also spread his fortune by giving $1,000 each to the three candidates.
Some GOP donors who backed Trump’s 2016 Republican primary opponents are now doing the same. Mike Murphy, who managed former presidential candidate Jeb Bush’s super PAC, Right to Rise USA, gave $1,000 to Sanford. Murphy reportedly pocketed $14 million from the $100 million the super PAC raised to boost Bush’s campaign.
Another former Bush supporter, Quan Zhou, managing partner at the IDG Capital, gave Weld $1,000. Ahead of the 2016 primary, he gave Jeb Bush’s campaign $2,700 and $15,000 to his affiliated political committees.
Jack Biddle, founder of Novak Biddle Venture Partners, gave $2,500 to aid Marco Rubio’s campaign in 2016. The venture capitalist and his wife, Foree Biddle, gave a total of $5,600 to Sanford’s campaign this cycle.