A section of particular concern is the female vote. Even in this campaign, he's had a dig or two at Clinton for playing the "woman card".
Well, his track record isn't any better. In 1994, he didn't want "to sound too much like a chauvinist", but continued to make some fairly interesting remarks.
"I have days where I think it's great," he said.
"And then I have days where, if I come home -- and I don't want to sound too much like a chauvinist -- but when I come home and dinner's not ready, I go through the roof," he added, commenting on his views on women in his life having careers.
In an interview with ABC, Trump compared the women in his life to buildings, saying: "I love creating stars. And to a certain extent, I've done that with Ivana. To a certain extent, I've done that with Marla. And I like that."
"Unfortunately, after they're a star, the fun is over for me," he continued. "It's like a creation process, it's almost like creating a building. It's pretty sad."
To be fair to The Donald, some women, according to recent polling, do support him (despite more recent comments about Fox News anchor Megyn Kelly and and former presidential rival Carly Firorina).
On his own former wife Ivana, who he hired in a role at his Atlantic City casino, Trump in 1994 added: "I think that putting a wife to work is a very dangerous thing.
"If you're in business for yourself, I really think it's a bad idea to put your wife working for you. I think it's a really bad idea. I think that was the single greatest cause of what happened to my marriage with Ivana."
“Ivana would get angry at somebody over the telephone, all of a sudden, who was at the casino, and she'd start shouting. And I'd say, 'I don't want my wife shouting at somebody like that, I really don’t want that.
"And a softness disappeared,” he continued. "There was a great softness to Ivana, and she still has that softness, but during this period of time, she became an executive not a wife."