This one really is a mystery. I'm sure by now you know your candids are under appreciated, but quality wise it's no lesser quality than your higher scoring ones. I don't think that elbow in the shot should have knocked you so low, so I wonder if it's the actual subject that people didn't like.
I remember seeing this during the voting and asking myself "how does he know he's a pimp?" At the time I didn't know it was your photo, although I should have since it screams Pawdrix. Since I didn't know it was you I thought the photographer was just stereotyping this guy and had I voted, it may have had an effect on the score. To most of the world pimps are just something we see in the movies.
If this photo were on a themed website that was documenting New York streets it would seem less out of place. In the DPC environment it seems like a photo of a snappy dresser being labeled as a pimp.
With that all said it's a very interesting photo. People always seem so relaxed and natural in your photos. These are definitely not people you'd see walking down Oregon streets, heh.
You have such a great ability to find interesting people for your shots. He kinda looks like Wesley Snipes. Of course, if it was him, I guess it would not surprise me. Interesting portrait of a snappy dresser.
I like how you caught the position of his feet - makes it looks like he's about to do a little dance. I find myself wishing he was a bit more isolated, without, particularly, that girl on the left coming out of his arm.
I have absolutely no idea whatsoever why this didn't score better.
The only thing I could possibly think of to do would maybe to have cropped it a little differently on the right to move him to the side of the image and possibly to lighten it to bring up his clothing.
Quite quirky! I would love to see him in color, though wondering what colors he's wearing adds to the charm. Your street shots are always awesome though, it just has a smaller group who appreciate them.