Donald Trump plans to throw Bill Clinton’s infidelities in Hillary Clinton’s face on live television during the presidential debates this fall, questioning whether she enabled his behavior and sought to discredit the women involved.

Trump will try to hold her accountable for security lapses at the American Consulate in Benghazi, Libya, and for the death of Ambassador J. Christopher Stevens there.

And he intends to portray Hillary Clinton as fundamentally corrupt, invoking everything from her cattle futures trades in the late 1970s to the federal investigation into her email practices as secretary of state.

Drawing on psychological warfare tactics that Trump used to defeat “Lyin’ Ted” Cruz, “Little Marco” Rubio and “Low-Energy” Jeb Bush in the Republican primaries, the Trump campaign is mapping out character attacks on the Clintons to try to increase their negative poll ratings and bait them into making political mistakes, according to interviews with Trump and his advisers.

Another goal is to win over skeptical Republicans, since nothing unites the party quite like castigating the Clintons. Attacking them could also deflect attention from Trump’s vulnerabilities, such as his treatment of women, some Trump allies say.

For Hillary Clinton, the coming battle is something of a paradox. She has decades of experience and qualifications, but it may not be merit that wins her the presidency — it may be how she handles the humiliations inflicted by Trump.

She would make history as the first woman to be a major-party nominee, yet she would also be viewed, in part, through the prism of her husband’s flaws. Some political allies and friends, while disgusted with Trump, see a certain cosmic symmetry at work: After decades of fighting what she once called “the politics of personal destruction,” Hillary Clinton will reach the White House only if she survives one more crucible of sordid and scandalous accusations.

“She is so prepared to be president, but holding her head high and staying dignified during the campaign is probably what will help her the most,” said Melanne Verveer, a longtime friend and former chief of staff to Hillary Clinton. “Trump is yet another way she will be tested personally — one of her greatest tests yet.”

Hillary Clinton has often flourished in the wake of boorish behavior: her husband’s affair with Monica Lewinsky, Kenneth Starr’s investigation of her husband, the congressional impeachment proceedings. Women rallied to her side during her 2000 Senate race after her Republican opponent, Rep. Rick Lazio, invaded her personal space during one debate, and they helped her win the 2008 New Hampshire primary shortly after Barack Obama dismissively said she was “likable enough.”

Yet Trump said he was determined not to fall into those traps.

In a telephone interview, he noted that women did not like seeing Hillary Clinton insulted or bullied by men. He said he wanted to be more strategic, by calling into question Hillary Clinton’s judgment in her reaction to Bill Clinton’s affairs — people close to the couple have said she was involved in efforts to discredit the women — and in her response to crises like Benghazi.

“Just getting nasty with Hillary won’t work,” Trump said. “You really have to get people to look hard at her character, and to get women to ask themselves if Hillary is truly sincere and authentic. Because she has been really ugly in trying to destroy Bill’s mistresses.”

Clinton, in turn, has begun attacking Trump over his refusal to release his tax returns, suggesting he has something to hide, and over his temperament and leadership abilities by describing him as a “loose cannon.” And political allies say that, in time, voters will see through Trump’s criticisms.