Is Donald Trump actually good at business?

Donald Trump signs documents at a desk in the Mar-a-Lago estate, Palm Beach, Florida, 1995 - the year he lost $900m. Photo / Getty

John Gillespie dug into his omelette with one hand and flipped through the Toledo Blade with the other. The news that Donald Trump had declared a USD$916 million (NZD$1.2b) loss in his 1995 tax return, and may have avoided paying income taxes for as many as 18 years, had made it to the front page of the local newspaper. Gillespie, 52, struggled to make sense of it.r

"This was in 1995?" he asked, looking up from the diner counter. "This was during an economic upturn - and he managed to lose $916 million?" The tool and die maker, who had voted for Sen. Bernie Sanders of Vermont in the Democratic primary, started to laugh. "That tells me a lot about his economic skills."

The story, first published by the New York Times late Saturday and not denied by a flustered Trump campaign, represented a piece of a holy grail that Hillary Clinton had sought for months. The Democratic nominee, who is making her first campaign stop in this city on Monday, has struggled to convince many traditionally Democratic voters that outwardly successful Trump is not to be trusted and poses a threat to their livelihoods.

The revelations about the Republican nominee's taxes gave Clinton a fresh opportunity. In conversations around Toledo, many voters said they were offended by Trump.

"It's disgusting," said Steve Crouse, 65, the owner of Toledo's downtown Glass City Cafe and a separate printing business. "As a businessman, he's got that right to do that. It's the way the laws were set up. But it's not right. I would feel guilty if I didn't pay anything. It's flat-out cheating the government. You're using all the roads, the fire department, the police, so you should pay for that."

On his way into church, at the suburban parish he shares with Rep. Marcy Kaptur, D-Ohio, Fred Glynn, 63, said that Clinton's support of abortion rights made her impossible to accept. But the tax story, which he had just seen on CNN, added to the reasons he would have to reject Trump.

"How can he not pay income taxes?" he asked. "He talks about helping people, but he doesn't pay income tax? That's helping everybody. It's like the situation in Florida, where he didn't pay taxes on his golf course. The school suffered from that."

Toledo, like the rest of surrounding Lucas County, is just one of many communities where Clinton was struggling to pull back loyal Democrats from Trump. The Republican nominee had visited the city twice, even filling the city's largest arena at a rally after the Republican National Convention. At every stop, as in the primary he lost here to Gov. John Kasich, R-Ohio, and as in the first televised debate, he decried the North American Free Trade Agreement for "killing our jobs" and promised to use tariffs and tough negotiations to jawbone trade partners into submission.

Democrats watched with horror as the message seemed to sink in. In 2012, President Obama won Lucas County in a two-to-one rout, netting 66,676 votes here on his way to a far narrower statewide victory margin of 166,272. This year, just 57,846 total votes were cast in the tough, contested primary between Clinton and Sanders. The same day, 52,350 votes were cast in the county's Republican primary. Since 2008, the Democratic primary vote had tumbled by 40 percent; since 2012, the Republican vote had doubled.

Separating Trump from his rhetoric by casting him as a dishonest and bumbling tycoon had been key to Clinton's fight back, but for months, it didn't penetrate. A TV spot that showed David Letterman revealing the China labels on Trump's branded clothing didn't move poll numbers. Clinton got little lift from a rally at the failed Trump Taj Mahal casino at Atlantic City.

"He built up his wealth by stiffing small businesses and contractors," Clinton said last month in a video address to the Laborers' International Union of North America. "My dad was a small businessman. I'm just happy he never did business with Trump."

News coverage of that speech - and Trump's mockery of it - focused not on that line, but on the loud and harried way Clinton said "You might ask, why am I not 50 points ahead?" And last week, a Fox News poll otherwise stuffed with good news for Clinton found that just 46 percent of voters were bothered by Trump's refusal to release tax returns, while 60 percent were bothered by the saga of Clinton's private email server.

If Clinton's campaign saw Sunday as a turning point, Trump's most devoted supporters weren't going along with it.

"He's a businessman, and he has lawyers," said Jane Pisano, 86, shrugging as she walked into Sunday Mass. "What bothers me more are the lies that Hillary has told. He didn't do anything to hurt our nation. She did, and she continues to do so."

One state over, at the crowded Pennsylvania rally that Trump held as the story broke, his fans offered similar spin. "Diamond" Mike Allen, a 55-year-old Trump supporter living in southeastern Pennsylvania, said it was absurd that someone leaked Trump's tax returns. Whoever did it, he said, should be sued - and had not dented his view of Trump.

"I want somebody who knows the loopholes," said Allen, a former wrestler who now does stand-up comedy. "I love it. That's the guy I want for president. If it was done legally, he deserves that, his employees deserve that. My hat's off to him."

Allen said that he paid federal income tax every year and that he always felt "ripped off." The government, he said, doesn't spend his money as carefully as he would. And he would rather that the wealthy pay their fair share through a flat tax, so he hoped that Trump would win the election and end special tax breaks.

"Who better to close that system down than him?" Allen asked. "I have total faith in him."

Sixteen Republican rivals had watched Trump coast on that argument, and trounce them in the primaries. But four years earlier, Democrats had held down Mitt Romney's support with working-class, white voters by branding him early and often as a plutocrat. Priorities USA, the cash-rich pro-Clinton super PAC that supported Obama that year, had made mini-celebrities out of workers who blamed Romney for lost jobs. The super PAC is on the air in Ohio now with the sort of spot that worked, showing contractors who say they were cheated by Trump in New Jersey.

And the tax returns gave Clinton an argument that would not have worked against Romney: that Trump's swagger covered up a record of business failure. In the 24 hours since the tax leak, the $916 million loss has proven the toughest aspect for Republicans to spin.

"He ain't that good," said Alex Pickett, 52, while waiting for a bus that would take him to a downtown church. "Can't be that good if he lost that much money."

On Sunday afternoon, at a bar near Toledo's resilient Chrysler complex, the size of Trump's loss was a punch line. As the Cleveland Browns blew a game against the Redskins, Ron Amborski, 57, marveled at what he had just seen on Sunday talk shows.

"Rudy Giuliani called Trump a genius at least 12 times," Amborski said. "Talk about over-compensating. 'He's a genius businessman! He made a genius comeback!' I thought, 'Man, if this was a drinking game, I'd be hammered.' "