[Xenalyte]

"How are we to explain the "smartest woman in the world's" repetitious use of "you know"?

The apostrophe indicates possession - in this case, "Hillary's use" - so it needs to go on the noun referring to the possessor, which would NOT be "world." It would be "woman."

That is really awkward, so I'd recast the question as:

How are we to explain the repetitive use of "you know" by the "smartest woman in the world"?

Or perhaps, since I am an inveterate smartass:

How are we to explain the repetitive use of "you know" by the alleged Smartest Woman in the World?

[Carolinamom]

I like your solution! When there's a bump in your sentence road, drive around it. ;)

[baubau]

Thanks.

I agree with rephrasing the sentence.

"How are we to explain the repetitive use of "you know" by the alleged Smartest Woman in the World?"

Recasting her into an "alleged" makes it clearer that smart she ain't. LOL!