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The Impeachment

Why Trump Would Attack: The Monica Lewinsky scandal raises many questions that could benefit Mr. Trump: Should Mr. Clinton again have a role in the White House after conducting such an affair on the job? Did Mrs. Clinton mistreat Ms. Lewinsky when she called her a “narcissistic loony toon?” And do voters really want to relive the dramas of the 1990s?

Why It Might Fail: Polls from the late 1990s showed that Mrs. Clinton’s popularity soared as the scandal unfolded, suggesting that Mr. Trump might actually help his opponent by bringing up the subject. Mrs. Clinton often responds by calling the controversy old news, and she could be correct that voters are tired of hearing about it.

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The Cattle Futures

Why Trump Would Attack: Old questions about how Mrs. Clinton managed in the late 1970s to turn a $1,000 investment in cattle futures into nearly $100,000 with little financial experience is a prime target for Mr. Trump because it fits into the theme that she is “crooked,” a narrative that he has been carefully cultivating. This line of attack also puts the debate on friendly turf for Mr. Trump, a billionaire businessman with plenty of experience investing.

Why It Might Fail: The cattle controversy never amounted to much, and resurfacing it opens up Mr. Trump to rebuttals about his many failed businesses and the lawsuits facing Trump University, which has been accused of fraudulent practices.