Just a thought here, so take it with a very large gran of salt.
I like the concept, but IMO the background is the killer. I think if you were to try this again, I'd really like to see gas pumps in the background, the ciggy in the corner of his mouth and a 40 in his lap. Have some motion blur on his right hand (as in frantically hoping for a winner) and an officer/GF/anyone in the side mirror. Also, take a half step to your right to get moer of his face/expression prominent. Kudos anyway.