One Tuesday evening last month, Donald Trump, the presumptive Republican nominee for president, arrived in midtown Manhattan for a fundraiser at Le Cirque. The swanky French restaurant prepared entrees of steak and roasted fish for the 60 guests, who had each spent $50,000 (U.S.) to attend.
For Mr. Trump, the event was crucial. His campaign coffers were all but empty while his Democratic opponent Hillary Clinton continued to add to her war chest. To close the gap, he had started to woo a group critical to any Republican nominee: the moneyed donors of New York's financial industry.
It is proving to be an uphill climb. While a handful of well-known hedge-fund managers attended the June event, many others who have donated to Republican candidates in the past were conspicuously absent. On Wall Street, the reaction to Mr. Trump tends to range from deep ambivalence to outright distaste.
In one respect, Mr. Trump is a dream candidate for the financial industry. He has repeatedly promised to dismantle the Dodd-Frank financial reform legislation enacted in the wake of the 2008 crisis. Banks view the law as overly onerous and costly to their business.
But in many other ways, Mr. Trump drives bankers crazy. He is unpredictable and prone to bash the industry when it suits him. (Back in January, he stated that he "wouldn't let Wall Street get away with murder.") He has yet to provide any detailed economic plan. Meanwhile, one of his favourite policies – scrapping U.S. trade deals – is wildly unpopular with Republican donors.
The result has been some strange moments. Paul Singer, a hedge-fund billionaire who gave millions to Republican candidates in 2012, is shunning Mr. Trump. At an event last week, Mr. Singer said that Mr. Trump's economic policies were "preposterous" and would nearly guarantee "a global depression."
A day earlier, Mr. Trump had delivered a tirade against American trade policy. As he spoke, the U.S. Chamber of Commerce – normally well-disposed toward Republican candidates – tweeted a point-by-point rebuttal. The president of a national association of manufacturers claimed Mr. Trump had things "backward" on trade.
"The optimists are saying, 'He's making all this stuff up,'" said one Republican hedge-fund executive who spoke on condition of anonymity. "But if he's turning the Republican Party away from free trade, that's a big deal and a bad thing." Plus, the executive said, Mr. Trump's unpredictability would wreak havoc on markets. "If the only thing I knew was that Donald was going to win, I'd sell."
When it comes to financial regulation, it's hard to know exactly what Mr. Trump endorses. He has made his hostility to the Dodd-Frank reforms clear – "It's a very negative force, which has developed a very bad name," Mr. Trump said of the law in May. But it's not obvious what, if anything, he would retain of the 2,200-page statute, which touches on everything from mortgages to derivatives to bank capital requirements.
What's more, major financial institutions have reconciled themselves in large part to the new regulations. For such banks, "Dodd-Frank is like Hillary Clinton – it's the devil you know," said Mark Calabria, an expert on financial regulation at the Cato Institute in Washington.
Mr. Trump has met with Jeb Hensarling, a senior Republican Congressman who has proposed a replacement for Dodd-Frank, but the presumptive nominee hasn't endorsed Mr. Hensarling's plan. Mr. Trump's campaign "hasn't really put out anything" in the way of detailed proposals for the financial industry, said Douglas Landy, a partner at Milbank, Tweed, Hadley & McCloy in New York whose clients include major global banks.
While bankers await specific policy proposals from Mr. Trump, they are also keeping a close watch on Ms. Clinton's choice of a vice-presidential candidate. Massachusetts Senator Elizabeth Warren, despised by Wall Street for her vehement critique of the industry, is reportedly on Ms. Clinton's short list. Ms. Warren "scares the heck out of people," said one banker at a major financial institution in New York, who spoke on condition of anonymity.
Home to moderate, mainstream Republicans as well as Democrats, Wall Street isn't a place where Mr. Trump has legions of fans, but he does have his defenders. His chief fundraiser, Steve Mnuchin, is a founder of hedge fund Dune Capital Management LP. Other supporters include legendary corporate raider Carl Icahn and distressed-asset investor Wilbur Ross, both billionaires.
"I think we need a more radical, new approach to government," explained Mr. Ross in an interview on CNBC in June. Mr. Trump will take the country in a "less politically correct direction."