I don’t think Hillary is a very good debater, based on her past performance. Trump isn’t either, but he wouldn’t be operating under the same playbook as her. If Hillary tries to play the “Woman” card, he will bring up the rape allegations against her husband, his activities with Monica Lewinsky, and probably her chief-of-staff’s husband Anthony Weiner. I don’t think Cruz would go there, but Trump definitely will. His challenge will be to avoid just being the guy who tears her down and instead establishing a positive persona in the eyes of the undecided viewers, and building his coalition beyond his avid fans.
He could do well by cutting into Hillary’s support among African-Americans. Clearly, rampant illegal immigration has hurt many of them. Entry level jobs are harder to get, skilled trades like housing construction are all but closed to non-immigrants in some parts of the country, and wages are driven down by continually increasing the supply of labor through immigration. This is an issue where black citizens would benefit from Trump’s policies. He could do a better job of articulating that.