As recent as 2010 we were finding major flaws in online poker security, here are a couple of videos I did of us sniffing hole cards out of the air because sites were lying about their use of SSL. They were using xOR encryption. Insane.
http://www.youtube.com/watch?v=4HBUe8Fb73Q http://www.youtube.com/watch?v=AAQDEXJdbQc