Someone suggested his current presswoman, Kat Pierce, half-black, sharp, and fearless. That should trump hillary.
However, Tea-Party Kat lost a congressional primary against Pete Sessions, so that is one major drawback against her.
And Bush Sr. has won? Chaney? Palin? OTOH he may want one of the ladies who has SUCCESSFULLY run a major corporation and understands business.
Iirc there are more female executive in his company than any other business Ivanka runs a “how to present yourself” type of workshop for women That’s how she knows her former pupil Chelsea.
That ws Katrina Pierson.
Her loss to Sessions was not a negative.
Her running in that race against republican incumbent Sessions showed she had moxie and political smarts.