His plummeting poll numbers suggest that he is cruising toward defeat in November unless he is able to drastically change course. But it is unclear how recent leadership changes will help Trump reverse his core problems: his murky message, his scattershot ground game, and his unwillingness to appeal to a broader group of voters.
Instead, Trump's restructuring of his campaign ushered in leaders who are practiced in the dark arts of politics, unafraid to dabble in right-wing conspiracy theories about Clinton's health, her marriage, and allegations that Bill Clinton has mistreated women.
Those kinds of stories have been a specialty of Steve Bannon, the executive chairman of the right-wing site Breitbart News, who is now the Trump campaign's chief executive. Bannon's addition to the team was a surprising twist that befuddled many Republicans Wednesday, given his lack of experience running campaigns. Trump's former campaign manager Corey Lewandowski likened Bannon to "a street fighter."
Will Ritter, a Republican political operative in Virginia who isn't supporting Trump, offered a biting assessment: "Another guy is going to ride the psychotic horse into a burning stable."
The addition of Bannon came in the same week reports surfaced disgraced Fox News executive Roger Ailes is serving as an informal debate adviser to Trump. Ailes recently stepped down from Fox amid a swirl of sexual harassment allegations and accusations that he used his power to spy on adversaries.
The elevation of Kellyanne Conway
, a respected Republican pollster, to campaign manager, spoke to Trump's desire for more people around him who he trusts at a time when his campaign is flailing.
Conway's new role was welcomed by some GOP operatives, who hope she can help Trump fashion a more succinct message to improve his standing among college-educated whites, particularly independents and women.
"The only thing I care about is the Trump team making this a referendum on Hillary Clinton's record and getting the country back on track," said Henry Barbour, a GOP strategist who has long been involved in helping to shape the message of the Republican Party. "If the new campaign leadership can do that, I am all for the change."
Neil Newhouse, a veteran Republican pollster, said that Trump's challenge is that "he is not able to stay on a message -- he diverts, he freelances and doesn't have the discipline to stay on a message."
"I think Kellyanne's presence may help him do that," said Newhouse. "Regardless of what that message is, she can help him be more direct, more consistent, and I think that's what he needs right now."
Campaign officials framed the staff changes as a typical expansion of the team weeks before early voting begins. But Trump's reshuffling signaled how he has chafed under the guidance of Campaign Chairman Paul Manafort, one of the few people around the real estate mogul who was unafraid to confront him about the shortcomings of his candidacy.
One source told CNN's Sara Murray that Trump's overall feeling is that he still has a chance to win, but if he loses he wants to lose his way, running the kind of campaign that he wants to run. That approach would mean more big rallies, freewheeling interviews on TV, and a streamlined focus on battleground states.
While building Trump's political team into a functioning campaign, Manafort was brought on to try to steady Trump and turn him into a more polished, disciplined candidate.
But Trump has exhibited obvious discomfort with that strategy as he has lurched from teleprompter-assisted speeches back to his volatile tangents and slashing personal attacks.
In a memo to staff on Wednesday, Manafort said the staff changes marked an exciting day for the campaign -- a new delegation of duties that would allow the team to expand their breadth and messaging capacity at a time when they are beginning to air television ads in key states.
Manafort said he would continue to focus on "the big picture, long-range campaign vision." Bannon, he said, would bring "a business-like, day-to-day leadership approach to the CEO position that's reflective of our leader, Mr. Trump."
Conway, who will now travel extensively with Trump, will help guide messaging, Manfort said.
"I think we're going to sharpen the message. We're going to make sure Donald Trump is comfortable about being in his own skin, that he doesn't lose that authenticity that you simply can't buy and a pollster can't give you," Conway told CNN's Alisyn Camerota Thursday on "New Day." "Voters know if you're comfortable in your own skin. Let him be him in this sense."
She also noted that while polling currently shows Trump trailing, it's actually something that's helpful.
"I think it helps us to be a little bit behind, and we are. It lights a fire under us, and reminds us what we need to do to get this done," she said.
Trump's new campaign manager also said a focus on the issues would help her candidate.
"The idea we have millions more in poverty, millions more out of work, the idea that people feel unsafe, that they feel less and less safe now, those are the issues we need to address," Conway said.
But with Bannon at the helm, Democrats are now bracing for a far more personal onslaught against Clinton this fall. It's a risky approach, however, given that Clinton's standing among voters has sometimes improved when she is perceived as the victim of attacks.
Robby Mook, Clinton's campaign manager, told reporters during a Wednesday conference call that the Democrat is expecting more divisive rhetoric from the new team.
"After several failed attempts to pivot into a more serious and presidential mode, Donald Trump has decided to double down on his most small, nasty and divisive instincts by turning his campaign over to someone who is best known for running a so-called news site," he said referring to Bannon's oversight of Breitbart News, "that peddles divisive, at times racist, anti-Muslim, anti-Semitic conspiracy theories."
"What's become clear from this is no matter how much the establishment wants to clean Donald Trump up, get him on a teleprompter and get him on message, he has officially won the fight to let Trump be Trump," Mook said.
Manafort, in his memo, insisted the campaign is in a strong position to win. But the current poll numbers do not breed confidence in a Trump victory.
"He does not just have a swing state problem, he has a national problem," said Newhouse. "Trump is not close enough in the swing states to target them and make a difference right now. He's got to move his numbers nationally before these key swing states come in play."
"The only thing that's leaving hope right now that Trump can turn this around is Hillary Clinton's popularity," he added. "If Trump is able to build on that, then potentially there is a path."