The feds can easily come down on bitcoin gambling sites if they want, especially if these sites make it clear that they are intended to be a replacement for real-money gambling, and not just people gambling meaningless internet coins.

Headshot is correct that a small operation is much less likely to see prosecution than a large operation (same reason Merge hasn't been busted yet, while Pokerstars was), but he is incorrect to say that there's a "0.0 chance" a small operation will get busted.

If you disagree with this and think bitcoin gambling is 100% legal according to US law, then you would be a fool not to set up your own bitcoin casino/poker room. Software can be had for as little as $100 (seriously). If this were legal, I would be the first one setting something up like this myself.

You do have less to lose if you are already broke and can't be smacked with big fines if caught (well, you can get fined, but the government can't collect nonexistent money). I have too many assets to be taking a risk with something like this, but honestly I still wouldn't be risking it even if I were broke.