The new New York regulations, which will likely be adopted by other States once tested and updated, will soon capture online gambling sites that primarily use Bitcoin.
Here is why:
s.200.2
(m) Virtual Currency means any type of digital unit that is used as a medium of exchange or a form of digitally stored value or that is incorporated into payment system technology. Virtual Currency shall be broadly construed to include digital units of exchange that
(i) have a centralized repository or administrator;
(ii) are decentralized and have no centralized repository or administrator; or
(iii) may be created or obtained by computing or manufacturing effort.
Virtual Currency shall not be construed to include digital units that are used solely within online gaming platforms with no market or application outside of those gaming platforms...Because Bitcoin can be used for other things than online gaming, it becomes a virtual currency. That means it can be captured by the online gaming laws in the USA, Unlawful Internet Gambling Enforcement Act of 2006.
If you offer online gambling using crypto and a US Citizen uses the services, then the operators of the online crypto gambling site will be arrested unless you get a licence in concert with a physical casino operation that is already regulated.
The lack of privacy in Crypto means that users can be traced and it can easily be proven that overseas gaming sites are allowing US Citizen to gamble. If you run such online gaming sites, those crypto coins you take as profits will follow you around until you set foot on US soil or come under extradition requests.
Here is the thing, given the demographics of the crypto space and the popularity of online gambling, there will be a lot of people caught by these regulations.
Operators around the world will no doubt have their details added to Federal arrest warrants. Users of online gambling, including sports betting and poker, are also potentially at risk of arrest.
Yeah, good luck with that non-anonymous payment option you're using.
Timeline: Internet Poker and the Law
http://www.washingtonpost.com/wp-srv/investigations/poker/time.html