The political outsider's unconventional style and resume vaulted him into the role of party standard-bearer, but his unusual background was also exposed repeatedly this week as a major liability, with characters -- real, or maybe even fictional -- re-emerging to hound him.
He was dogged by questions surrounding his vast fortunes, his edgy media profile and his less-than-savory associates.
Perhaps no controversy better illustrated Trump's break from typical politics than his repeated refusal to release any tax returns, bucking decades of presidential tradition. The presumptive GOP nominee has allowed that he will release returns eventually — but only when he is cleared of routine audits that his counsel says should preclude their release.
Could he release just the effective tax rate in advance?
"It's none of your business,"
Trump told ABC News on Friday. "You'll see it when I release."
Trump told The Associated Press this week that his tax information was not newsworthy or enlightening, and would not signal much about his billions of dollars in wealth. But those billions show just how different Trump is from your ordinary candidate: No one of Trump's wealth has ever become president before.
Clinton wades in
His refusal quickly became fodder for Hillary Clinton, Trump's all-but-certain Democratic opponent, who stirred the pot by wondering aloud about what might be in them.
"So you have got to ask yourself, why does he not release them?" she said in Blackwood, New Jersey, on Wednesday. "Because when you run for president, especially when you become the nominee, that is kind of expected."
But Trump is not an "expected" nominee — a departure shown vividly by the return of personalities from his colorful past.
First, there was Anthony Senecal, the longtime butler at Trump's estate in Palm Beach, Mar-a-Lago, who, as Mother Jones
first reported, said Obama "should have been taken out by our military and shot as an enemy agent in his first term."
Senecal has no formal role with the Trump campaign, but the billionaire is bringing some of his former hands and friends -- often rough around the edges -- into the presidential spotlight.
And it's not always a good look.
"Either way, I don't care. Hanging, shooting -- I'd prefer he'd be hung from the portico of the White House, or as I call it, the white mosque," Senecal said of Barack Obama in an interview
with CNN. "Does it sound like I'm nuts? Because I'm not."
The Trump campaign quickly disavowed Senecal, but the next day, other figures from Trump's past -- or, rather, two pseudonyms -- surfaced: John Miller, or sometimes, John Barron.
Trump on Friday was consumed by questions about whether he had posed as imaginary individuals with those names in order to deal with reporters' queries about his love life or personal sagas.
Trump's defense? "It was not me on the phone," he told NBC on Friday morning.
Trump himself had largely admitted to using the name of John Barron in court testimony in 1990. But on a day when he could've been trumpeting new signals of unity from party leaders like Paul Ryan, Trump aides instead spent much of the day arguing that he had not posed as his own spokesman three to four decades ago.
Trump himself, however, wasn't interested in rehashing his past.
"You're going so low to talk about something that took place 25 years ago whether or not I made a phone call?" Trump said on NBC. "Let's get on to more current subjects."