
Chris Simon has all the history to be the Islanders dirtiest player. Over the course of his 15 year career, he has been suspended 8 times for a total of 65 games. That's almost an entire season spent under suspension. His suspensions have been for a wide range of offences including slashing, crosschecking, kneeing, suckerpunching, elbowing and using racial slurs.
(Wikipedia) In 1997, during a game against the Edmonton Oilers, Simon allegedly called Edmonton forward Mike Grier a [racial slur]. Although the spoken words were never confirmed, he was suspended three games as a result of the incident.
Simon was suspended for one game in a 2000 playoff series against Pittsburgh for cross checking Peter Popovic across the throat. He was given two-game suspensions once in April 2001 for elbowing Anders Eriksson, and twice in 2004 for cross checking Tampa Bay's Ruslan Fedotenko and then jumping on and punching him, and for kneeing Dallas's Sergei Zubov.