the guy was consistently moving a large amount of btc (to drug traffickers) , without a money transmitter license , aka felony money laundering , per the law ... just so anyone else out there is aware - you CANNOT as a private citizen in the U.S. legally buy or sell over $5000 worth of any type of currency in a single day without a money transmitter license ... whether that's btc/pesos/euros/seashells/usd , if you're converting currency , there are legal restrictions on what you can and cannot do ... he broke the law , and now is in jail ... i wonder why nobody wants to give free money to a criminal money launderer ? ? ?
He did have a money transmitter license. He owned Bitinstant which was legally registered in New York. You were only legally allowed to purchase $1k in BTC per day, however he found out that a user with connections to the silk road was bypassing the $1k/day limit. He then got nailed for his relationship to the Silk Road through that intermediary.
There are additional details in the case, but that is the gist. I dont know, I am personally a fan of Charlie Shrem, I am of the opinion that if this was a standard USD business and not a BTC business in question, he would have got a slap on the wrist and a warning that what he was doing could be considered illegal. People are quick to defend him, because this was one of the first cases of pretty openly biass of law enforcement targeting a Bitcoin business to send a message.