[2] During the 1990–91 OHL season, Simon served a 12-game suspension for slashing David Babcock in the face, breaking seven teeth and opening a gash that required 21 stitches.

Simon was involved in numerous on-ice incidents and was suspended eight times by the NHL for his conduct, for a grand total of 65 games.

[13] According to ESPN's Barry Melrose, Hollweg escaped serious injury because Simon's blow caught his shoulder pads before hitting his face.

[citation needed] Simon was automatically suspended indefinitely by the NHL due to his match penalty pending ruling by the league commissioner Gary Bettman and disciplinarian Colin Campbell.

[18] On December 15, 2007, at 14:06 of the third period of a home game against the Pittsburgh Penguins, Tim Jackman and Jarkko Ruutu exchanged words between the teams' benches during a stoppage of play.

The incident was witnessed by referee Justin St. Pierre, who assessed Simon a match penalty for attempt to injure and ejected him from the game.

The following Monday, Simon agreed to go on indefinite paid leave from the team, saying there was "no excuse" for his actions and that he needed some time away from hockey.

League disciplinarian Colin Campbell said that in his opinion, Simon had "repeatedly evidence(d) the lack of ability to control his actions," and also stressed that this was his eighth disciplinary hearing.

[citation needed] After Chris Pronger was not initially disciplined by the NHL when he stomped on Ryan Kesler's leg on March 12, 2008, Simon decried what he saw as unfair and unequal treatment.

[28][29] Simon was suspended for one game during the 2000 Stanley Cup playoffs for cross-checking Pittsburgh Penguins' Peter Popovic across the throat on April 13, 2000.

He was given two-game suspensions, first on April 5, 2001, for elbowing Anders Eriksson, and twice more in 2004 for cross checking Tampa Bay Lightning's Ruslan Fedotenko and then jumping on and punching him, and for kneeing Dallas Stars's Sergei Zubov.

As a teenager, he struggled with an addiction to alcohol but was helped to sobriety by future Buffalo Sabres and New York Islanders coach Ted Nolan in 1992.

In the filing, a doctor testified that Simon had symptoms of chronic traumatic encephalopathy (CTE) which were believed to be attributed to significant brain trauma during his hockey career.