Consider his CV: He came up with George H.W. Bush when the latter was chairman of the RNC, back in 1972-3. He came to Bush's attention with some dirty-tricks fight with another guy over a Republican Party post; Bush stepped in, thought, "gee, cool" and promptly ran the other guy out of the Party and hired Rove.
Rove was there in 1980 with "Poppy" when it was time to blackmail Poppy's way onto the ticket, and he was there when Bush cashed in his patronage by giving away the store to the "pigs at the trough".
Later "Turd Blossom" was reassigned to "baby-sit" (locution of another pro pol telling stories) the bibulous, hell-raising Dubya, who at the time was exhibiting an acute case of "preacher's son". And everything else flowed from that.
But the larger point is, Rove was tight with The Old Man back when Poppy was New-World-Ordering. So yeah, Rove knows lots of creepy people in black limousines.