I've won contests and waited a lot longer than a couple months, but my rule of thought was that if something is free, and a timeline is not given, its hard to demand anything. If he never talked to anyone, or is sending email to an account that is a void, its not the same thing as getting screwed over.
It looks like you started a thread with an inflamatory title, and aren't really involved. I know its become a popular way to get what people want on the internet, but I can tell you right now that its not needed. Did he win a product that is currently in production, or is it an upcoming new rail that isn't being built yet? There are a lot of questions that can't be answered by you, but your thread title doesn't take any of that into account.
I've dealt with the guys at DD numerous times, and there are plenty of people on this board, including myself, who are classed as "little guys". I think you will find that DD has bent over backwards to help their customers, and without any name calling or slander being involved.
If your friend is legit, tell him that he can email me at firstname.lastname@example.org, and I'll try to help him out or make sense of what is happening. No drama, no name calling, just firearm owners helping each other out. Believe it or not, thats what most of the guys on this board are here for.