I am sure that HRC's campaign has a thick file on Trump. It just seems to me that HRC is not very adept on her feet. Trump is pretty good on his feet (most of the time).
I don't think that much of general electorate knows about (or remembers) the Clinton legacy of Whitewater, her former lovers (including those who mysteriously died like Vince Foster), the $2B the Clinton foundation has funneled through its coffers (including $ from Saudi Arabia, Russia, Qatar, China, etc.), the Clinton connection to the Panama Papers - the list goes on an on. Her criminal behavior with the emails (they are felonies) don't matter? If you did this, you'd be in jail and paying a huge fine, so would I. The Obama Administration cover-up of Benghazi, of which HRC played a key role?
HRC thinks she's above the law and she acts like it. She also is one of the worst politicians when it comes to identity politics - female vs. male, black vs. white, gay vs. straight, Muslim vs. Christian, pro-choice vs. pro-life. there is almost nothing she does that unites this country in any way. Except of course if its to continually demonize white males.