Priorities USA will spend $6 million on ads between May 18 and June 8, hitting Trump in Ohio, Florida, Virginia and Nevada, all general election battleground states. The ads will try to do what no Republican could: Take down the businessman who beat a scrum of veteran politicians to all-but-win the Republican nomination.
"Donald Trump is a divisive, dangerous, con man who should never be President of the United States," said Justin Barasky, spokesman for the super PAC, who added that the super PAC is airing ads to show, in part, that it is preparing "for a close and competitive election."
Both of the first ads, named "Speak" and "Respect," use Trump's own comments to cast the presumptive Republican nominee as anti-women.
One of the Priorities ads utilizes a variety of actors, clad in Trump t-shirts, mouthing his words about Megyn Kelly, his daughter, Ivanka, and other women, before asking the viewer: "Does Donald Trump really speak for you?"
Likewise, another ad uses similar statements from Trump with footage of the man himself, before asserting "Donald Trump is wrong for us."
Trump responded to the ads in a series of tweets Tuesday, including one that called Clinton's husband, former President Bill Clinton "the WORST abuser of woman in U.S. political history."
"Crooked Hillary Clinton put out an ad where I am misquoted on women. Can't believe she would misrepresent the facts! My hit was on China," he tweeted.
Trump's attorney Michael Cohen said Tuesday on CNN's "New Day" saying they will ultimately hurt Clinton.
"Hillary Clinton's biggest problem is she has the lowest in terms of favorability amongst men so she has to stick with the women, otherwise she's going to be blown out of this race," he told CNN's Chris Cuomo. "She's going to turn around and try to create this gender warfare between Trump supporters and Clinton supporters. Unfortunately for her, it's not going to work because women understand Donald Trump is not sexist. He's not misogynistic."
"So when it comes down to these sort of Super PAC ads attacking Mr. Trump, it's going to end up coming back to bite her," Cohen added.
Priorities, an outfit tasked with raising millions of dollars and spending it on television ads, has previously announced that they would spend $130 million in ads that will begin airing ads on June 8, the day after primaries in California and New Jersey.
But the group is now moving up those ad reservations in an attempt to start Clinton world's pivot to the general before Vermont Sen. Bernie Sanders, Clinton's Democratic primary challenger, is officially out of the race. Clinton's campaign, which is still raising primary dollars and pledging to campaign in primary states, has been unable to make that turn.
How Priorities will define Trump is still unclear, and people close to the group declined to preview the content of their first ad.
Some Democrats -- including those associated with the Clinton campaign -- have tried to cast Trump as ideologically incoherent and out-of-step with many in his party. The strategy allows Clinton's campaign to court Republicans dissuaded by Trump.
Other Democrats -- namely those tasked with retaking majorities in the Senate and House -- have tried to cast Trump as the standard-bearer for the Republican Party, tying vulnerable Senate and House candidates to the presumptive nominee.
Priorities USA has now reserved $136 million in ads, $96 million on TV, $35 million on digital, and another $5.3 million on radio.