Cadillac's have Vertical headlamps and Taillamps. Maybe if the lamps were rotated up like | it would be more of a Caddy. I like your ambition in deisgning this though, but it screams New Lincoln and Audi.
Perhaps this could work well as a Chrysler as well? Looks like a New 300 to me.
I'll throw up a more Cadillac esque one this weekend as it's not getting big support as a Caddy, that's cool and I respect that. I'm a big Audi fan so I'm flattered by the comparison. Chrysler also sounds like an interesting idea as I think with a few touch ups it could have some 300C flavour.