Wall Street can't seem to make its mind up about who it wants in the White House.
In a business that leans decidedly conservative, many are saying the divide about which candidate the finance industry backs highlights the election's especially volatile tone, as well as Wall Street's desire to not be dragged back into the spotlight and further scrutinized.
"Nobody wants a repeat of 2008," one source said. "No one here wants to be seen as being elitist."
Until he sewed up the nomination earlier this month, Donald Trump had no need for Wall Street's elite, their money or their opinions. But as the candidate now must amass around $1 billion to fend off Democrat Hillary Clinton's campaign war chest, Trump has begun New York meetings with wealthy potential donors in an attempt to lure cash thanks to his growing influence. So far, according to a spokeswoman for his campaign, things are going well.
"The fundraising operation has been a tremendous success," she said in an email. "Mr. Trump has widespread support and the money is pouring in."
Trump is slated to attend a fundraiser Tuesday in New York. Prominent Wall Street names expected to attend include Stephan A. Feinberg of Cerberus Capital, real estate magnate Peter Kalikow and vulture capital leader Wilbur A Ross, according to the New York Times.
But not every Wall Street conservative has signed on for his cause.
Part of the problem may be perception. Several finance professionals, all asking to remain anonymous because they were not authorized to speak on the record, said there's an especially large stigma that has been applied to the Trump campaign with which professionals are ill at ease. Among the concerns Wall Street privately confided in having with the GOP candidate are his hostile language toward Mexico and Muslims and vague statements regarding policy and potential appointees to key positions in an administration.
Last week Trump met with a small cadre of New York campaign backers, including high-ranking real estate executives, according to reports. A source who has attended various political fundraisers over the last year said Trump will need to succeed with the finance set in campaign fundraising, and it's unclear whether top bankers and traders will be willing to cut checks at this point.
"I cannot think of anyone I know who's willing to publicly support Trump," one banker said. "But he's still got a lot of support."
Wall Street professionals are in near-universal agreement that wading into a controversial election cycle at a time when they've already been either pilloried by some candidates, or had relationships with other candidates (notably Clinton) scrutinized, there is little to gain from making their feelings known.
"I think people are aware of how much [Clinton] came under attack from [Vermont Democrat Bernie] Sanders," one source said. "No one out there wants their name or their firm brought up in a debate."
While Trump's campaign still has to build inroads and make new connections to raise funds, several sources said Clinton's existing relationships in New York are expected to help guide her fundraising. Trump may still need to further court Wall Street supporters, but a source suggested Clinton might aim to downplay her relationships with the industry. He speculated that it is unlikely the Democratic candidate would make any fundraising speeches at Wall Street firms.
The Clinton campaign did not respond to a request for comment.
Several expressed surprise that the GOP would have such a difficult time cobbling together support for any candidate, given Trump's opponent.
"You'd think the natural thought would be to support her opponent," one source said. "It's not the case, and that's what makes this whole situation so unique."