Campaign officials believe the strategy is a no-brainer. Focus groups and public opinion polls show huge swaths of voters turned off by Trump's pronouncements: immigrants, minorities, women, the disabled.
But the tactic carries risk. A lot of people like what Trump says; he emerged from the Republican convention in Cleveland last week even with or ahead of Clinton in several polls. Where some critics see behavior unbecoming a president, many voters see a willingness to take on political correctness and upend longstanding norms. It's the reason they're voting for them.
And Clinton is putting to the test a theory that was already proven wrong once. During primary season, Trump's Republican opponents were certain that Trump's insult-hurling style would doom his path to the nomination. They were wrong.
Kellyanne Conway, a senior adviser to the Trump campaign and a longtime GOP pollster, said in an interview this week that voters are so upset with the status quo - and so mistrustful of Clinton - that "distrust will trump distaste.
"Those are the voters who may have once prioritized tone and temperament," she said.
"Now, their priorities have changed. What's going on is so bad, the angst is so real, that people are willing to take the chance."
Clinton is not trying to change hearts or minds among voters who like what Trump has to say. Rather, it's to repackage his words and hurl them at strategically important blocs of voters in battleground states, so they are constantly exposed to the Trump words they find most offensive - and motivated to vote against him. Democrats say it's a tactic his Republican opponents failed to execute.
A recent spot called "Role Model" shows young children watching as Trump voices insults and profanity on a television screen. It is aimed at suburban families, mothers in particular, who the Clinton campaign believes are prime targets in this election.
For Latino audiences, no line is more potent, Democrats believe, than Trump's claim that undocumented Mexican immigrants include criminals and rapists.
"My father is not a criminal or a rapist, in fact, he's a United States veteran," said Latina actress Eva Longoria on Monday night.
Then, minutes after video footage of Trump mocking a disabled reporter played, Anastasia Somoza came onto the stage in her wheelchair.
"Donald Trump has shown us who he really is," Somoza said. "And I honestly feel bad for anyone with that much hate in their heart."
An ad from the super PAC Priorities USA, about a disabled named Grace, hammered home the same point.
"The children at Grace's school all know never to mock her," Lauren Glaros, an Ohio woman whose child has a disability, said in the ad. "And so for an adult to mock someone with a disability, it is shocking."
There was no subtlety in these messages, and that was the goal. The pitch is straightforward: Donald Trump is who he says he is.
"I don't think you can find any Republican who can defend some of the stuff that Donald Trump is saying," said Jamie Harrison, chair of the South Carolina Democratic Party.
The party faithful in the convention hall needed no convincing.
"Your word really identifies who you are and what you believe," said Jeion Ward, 62, a delegate from Virginia and a member of the Virginia House of Delegates. "He wouldn't really say that if he didn't believe it, right?"
But Harrison said Democrats are also aiming squarely at moderate voters not in the room, whom Democrats hope will do a double take when confronted with evidence of Trump's core beliefs.
"It's for independents and it's for moderate Republicans who are fiscally conservative but who like to think of themselves as moderate on issues like equality for the LGBTQ community, equal treatment for minorities, people who don't think that we need a religious litmus test in terms of entrance and exit for our country," Harrison said.
According to a recent ABC News/Washington Post poll, Clinton ties or leads Trump on a number of issues ranging from trust to temperament. But when it comes to change, Trump has a slight advantage: 46 percent say he would do more to bring about the change needed in Washington, while 44 percent say Clinton will.
Clinton's campaign chairman, John Podesta, acknowledged that her challenge remains to win over voters who are entertained or intrigued by Trump.
"Some people like it. It works on reality TV," Podesta said at a Wall Street Journal lunch this week. "But having a temperament that is quick to anger, discounts study, is impetuous, is probably never before been thought of as a qualification for putting your finger on the nuclear codes."
"I think that while it has some appeal to certain people who are entertained by it, I think it's also quite dangerous," he added.
The project began in earnest when Clinton delivered a foreign policy speech in early June that was devoted exclusively to deriding Trump's statements. She mocked the real estate mogul and painted him as unserious and dangerous.
One worry for Democrats is that Trump's political rise would "normalize" his rhetoric, desensitizing voters to comments or behavior that were once seen as out of bounds in politics.
"We have to call out this behavior and his often times racist and bigoted and fascist appeals," said former Maryland Gov. Martin O'Malley.
But O'Malley warned that disqualifying Trump "isn't enough."
"We have to lay out our story and agenda in a positive way," he said. "You have to do both: do what's morally responsible by calling out the opponent so he can't scapegoat people and vilify, then turn to our issues in a big way."
Voters may already be shrugging off the near-constant attacks on Trump, said Republican National Committee spokesman Sean Spicer.
Spicer said the RNC is ready on several platforms - digital, television, social media -- to counter each night's various criticisms of Trump but doesn't see that effort as a dominant part of the convention since mogul is so well-known and few if any barbs have become major stories.
"We did some fact check, sure. But we're looking at the Democrats' hypocrisy and mistakes and we want to make sure we expose their flaws and their messaging," he said.
