Question:    Can I go to jail for gambling online?

Answer:    To the best of my knowledge, no poker player has ever faced charges for gambling in an online casino. Therefore, there is more probability of winning the pot than getting in trouble playing a game of poker.
Only one American has ever gone to jail over criminal charges relating to Internet gambling. That unlucky fellow is Jay Cohen, owner of the World Sports Exchange online sports book. On March 28, 2000 Cohen was convicted in a New York federal court for one count of conspiracy and seven counts of violating the Interstate Wire Act of 1961. Cohen was sentenced to 21 months in prison, two years of supervised release, a special assessment of $800, and a fine of $5,000. He is currently free on bond. Keep in mind, though, that Cohen was the OWNER of the sports book - a bookie - and not a PLAYER.