Ron Gidwitz, Dan Webb and William Kunkler are veteran Republicans — and friends — from Chicago’s political money circuit. They raised buckets of cash for Mitt Romney four years ago. This time, however, their party’s nominee has sent them spinning off in three directions.
Gidwitz is hosting fundraisers for Donald Trump. Webb wrote a big check for Hillary Clinton. And Kunkler won’t do anything for either candidate, saying he prefers not to enable “stupid behavior.”
“Everyone is trying to make the best of a bad situation,” Kunkler said.
Illinois is especially ripe for this hodgepodge of political feelings. Republican Gov. Bruce Rauner pretends Trump doesn’t exist, Republican Sen. Mark Kirk trashes him, and the state’s top GOP donors, mostly moderate business leaders, squirm at his racially charged comments.
It’s also a tale in miniature of the Republican fundraising scene across the country. Many top donors boycotted or sulked their way through the national convention last month. And nearly every day, it seems, a Republican endorses Clinton, some promising financial help. In a speech Thursday denouncing Trump as a bigot, Clinton said she is “honored” to have that kind of support.
While big crossover donors like Webb are rare so far, there’s evidence that many Republicans are taking the Kunkler route of sitting on the sidelines, an Associated Press analysis of Federal Election Commission filings found.
Of the nearly 25,000 people who made the maximum contribution to GOP candidates other than Trump in the primary, about three dozen have since maxed out to Clinton. Trump has picked up only about 100 donors from that same universe.
Webb backed New Jersey Gov. Chris Christie, a fellow former U.S. attorney, in the primaries. Even then, though, he was open enough to Clinton to write her campaign a $2,700 check in May 2015 when one of his clients requested it.
Still, Webb planned to back the GOP nominee. He thought he’d be OK with Trump, liking the New Yorker’s not-so-conservative social positions and taking note when Christie endorsed him.
Then came the nominee’s Memorial Day weekend assertion that a Mexican judge’s heritage made him ineligible to handle a case involving Trump. Webb started thinking — about Trump’s remarks on the appearance of various women, the pronouncement that foreign Muslims should be temporarily barred from entering the country.
Webb concluded that Trump failed the “grandkids” test: Could he explain to children why he supports the GOP nominee? The answer was no.
Webb shared his views with friend Lanny Davis, a longtime Clinton backer and Washington attorney, who put him in touch with J.B. Pritzker, one of the Democrat’s top Chicago financiers.
Pritzker didn’t need to give him the tough sell. In mid-June, Webb wrote a $75,000 check to Priorities USA, the pro-Clinton super political action committee that can accept unlimited donations.
Now Webb is helping to organize a fall “Lawyers for Hillary” fundraiser in Chicago and trying to win over other Republicans.
“My pitch is, ‘You cannot sit on the sidelines,'” he said. “It has to be country over politics. We can stand up and just support her.”
Still, he’s not ready to turn in his GOP card. He said he hopes Trump will prompt the party to do some soul-searching that leads to a more inclusive posture.
“Sometimes you have to fail and destroy yourself before you can rebuild,” he said.
Webb hasn’t seen Ron Gidwitz in a while, but he knows what his friend is up to: Raising money for Trump.
A supporter of former Florida Gov. Jeb Bush in the primary, Gidwitz joined Trump’s fundraising team after meeting with him about two months ago. Gidwitz said he found the nominee to be “personable, persuasive and quite engaged.”
He’s since hosted Trump at a July fundraiser and is organizing a September event.
Gidwitz said he is approaching his fundraising duties as a realist rather than a die-hard Trump backer.
“Do I agree with everything he has said? No,” Gidwitz said. “But it’s not a question of how I feel; it’s how the donor might feel.”
His pitch: Picture Clinton in the White House. Do you want her naming Supreme Court justices? Do you want her to win in a landslide that sweeps away the Republican Senate majority?
“Those are the touchstones for me,” Gidwitz said.
Despite the efforts of Gidwitz and others who have organized more than 50 fundraisers with Trump, the confused universe of large Republican donors limits how much Trump can raise to compete with Clinton.
In June and July, after the two nominees became clear, Trump landed about 1,300 contributors who hit $2,700 or more, compared to 8,000 who did so for Clinton in those two months, the latest finance reports show. Donors can give a total of $5,400 to each candidate for the primary and general.
Trump is stronger with small contributors. People giving $200 or less made up well over half of his campaign’s income last month.
Kunkler, however, is contributing to no one.
“Ron knows not to even ask me,” Gidwitz’s friend Kunkler said. “I think what I’ve said to him is, ‘I respect your choice, but I sure have a hard time understanding your choice.'”
Like Gidwitz, Kunkler was a Jeb Bush fan. But Kunkler said he’s ignoring this race.
At a bipartisan immigration reform panel earlier this month, Kunkler lashed out, saying he hopes Trump and his supporters are “humiliated” on Election Day.
“That may have been a little over the top,” he said afterward. But he said he’s distraught that Trump has taken over his party.
“I just want us to learn,” he said. “I’d rather have us lose than have someone so bad that he keeps us out of the White House for three or four cycles.”
Associated Press writer Chad Day contributed to this report.