Is Mr. Trump worried about his brand?
Mr. Trump is already the most disliked presidential nominee in the history of polling, and his reputation is unlikely to recover if he continues to peddle conspiracy theories about election fraud and mock the looks of the women who have accused him of sexual assault. Another slashing performance against Mrs. Clinton could push away even more undecided voters — though at this point there may be few swing voters left for Mr. Trump to alienate.
Can Mrs. Clinton find the right tone?
Mr. Trump is not the only one confronting a stark choice about how to proceed. With her campaign expanding to compete in traditionally Republican-leaning states and her advantage growing in most of the battlegrounds, Mrs. Clinton is well positioned as the race enters its final days. Because Mrs. Clinton is now so heavily favored to win, the debate offers an opportunity for her to start looking beyond the election and toward unifying a country that has been divided by an ugly campaign.
Will Mr. Trump torch his own party?
Snubbed by Mr. Ryan in the final month of the campaign, Mr. Trump has seemed as eager to attack turncoat leaders in his own party as to make the case against Mrs. Clinton. He has reserved special venom for Mr. Ryan, blasting him as a weak leader with bad ideas about trade and immigration, and suggesting that Mr. Ryan might be sabotaging Mr. Trump’s campaign to pave the way for a presidential run of his own in four years.
Will Mrs. Clinton seek to reposition herself?
Republicans have been overjoyed that the WikiLeaks hacks of Mrs. Clinton’s private speeches and the email account of her campaign chairman have offered new fodder against her, or have at least diverted attention from Mr. Trump’s inflammatory campaign. But the revelations to date have done more to confirm the suspicions of those on the far left than those on the far right: Namely, that she is a cautious, at times plotting, left-of-center Democrat given more to pragmatism than purity.
Will sexual assault dominate the debate?
After a week’s worth of sexual assault and harassment accusations against Mr. Trump, there may be moments that feel more like a courtroom drama than a conventional presidential debate. Mr. Trump has never convincingly rebutted the numerous stories from women who say he groped them without consent. On the contrary, he has veered from ridiculing his accusers to asserting flatly, and falsely, that their stories have been debunked.