[Alain2]

Is the following sentence correct? It sounds very awkward to me:

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Wilson's live talks routinely draw 300 to 600 people, with them literally driving eight hours one way to see him.
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Naturally "with them" refers back to the people, but this sounds to me like the person who wrote this is saying "them drove 8 hours," and I'm wondering if I'm just being really old fashioned or if this sentence is actually incorrect.

Thank you for your help,

Alain

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[CMM_Kaleido]

I think your instinct is right on this one. As I understand it from The Gregg Reference Manual a prepositional phrase (with them driving.. . ) may be used as a noun, an adjective, or an adverb.

In this case, the phrase is not a noun or an adverb (it does not modify the verb "draw"). It is an adjective that modifies "talks" (the talks drive eight hours) This is not what the writer intends.

The sentence would be better off reading something like this
"Wilson's live talks routinely draw 300 to 600 people. Many of these people drive eight hours one way to see his presentations."

Or

"Wilson's live talks routinely draw 300 to 600 people who drive eight hours to see them."