The plan has three major thrusts: Portray Mr. Trump as a heartless businessman who has worked against the interests of the working-class voters he now appeals to; broadcast the degrading comments he has made against women in order to sway suburban women, who have been reluctant to support Mrs. Clinton; and highlight his brash, explosive temper to show he is unsuited to be commander in chief.
American Bridge, a pro-Clinton “super PAC,” has formed a “due diligence unit” of tax and business experts who are poring over Securities and Exchange Commission documents and court records related to Mr. Trump’s business career.
A staff member for an affiliated group, Correct the Record, which coordinates with Mrs. Clinton’s campaign, has collected footage of comments that have not hurt Mr. Trump’s standing among Republican primary voters, but that could be stitched together in what the group’s founder, David Brock, described as a montage of hateful speech that would appall a general electorate.
“They’ll flip their top, and they’ll flip their panties...” read the subject line of a recent news release from Emily’s List, a group that works to elect Democratic women who support abortion rights. The quote came from comments Mr. Trump made about women on “The Howard Stern Show” in the 1990s, unearthed by BuzzFeed last month.
Those types of comments, spoken by Mr. Trump over the years as he served as a tabloid regular and reality TV star, could help Mrs. Clinton excite suburban women and young women who have been ambivalent or antagonistic toward her candidacy.
Stephanie Schriock, the president of Emily’s List, said that an expanded research shop at the organization had compiled “an endless amount of misogynistic and outrageous comments towards women.”
The strategy highlights a concern among Mrs. Clinton’s allies that her chance to become the first female president has not led to widespread excitement among young women. Mr. Trump is the perfect solution to the enthusiasm gap, many Democrats say.