Simon grew up in
Wawa, Ontario, playing his minor hockey for the Wawa Flyers of the NOHA. As a Bantam, he played Jr.B. hockey for the Sault Ste. Marie Thunderbirds of the NOJHL in 1987–88. Simon was selected in the third round (42nd overall) of the 1988 OHL Priority Selection by the
Ottawa 67's. As a teen, he fought addictions and served an eight-game suspension for a stick-swinging incident while on the 67's. Simon subsequently became sober and counselled indigenous youth on the dangers of alcohol. 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. The
following season, Simon was suspended eight times for a total of 34 games, on two of those occasions by his own team. Simon was of
Ojibwa descent, and was born in Wawa, Ontario. Simon was seen as a role model to Indigenous Canadians for his accomplishments in the NHL.
Suspensions 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.
Mike Grier incident On November 8, 1997, during a game against the
Edmonton Oilers, Simon was suspended three games for directing a racial slur at Edmonton's
Mike Grier. Grier allegedly made derogatory comments about Simon's Ojibwe heritage, and Simon allegedly responded with a racial slur towards Grier, who is black, although the words spoken between the two players were never confirmed. Simon flew to
Toronto to apologize to Grier, who accepted. Grier and Simon were later teammates for a brief time in 2002 with the
Washington Capitals.
Ryan Hollweg incident On March 8, 2007, the Islanders faced their
rival, the
New York Rangers, at the
Nassau Veterans Memorial Coliseum. At 13:25 of the third period, Rangers forward
Ryan Hollweg checked Simon from (what Simon felt was) behind, knocking him face first into the boards, and giving Simon a
concussion. No penalty was assessed, and play continued. Simon then took a two-handed baseball swing in the face of Ryan Hollweg with his hockey stick as he skated by. Simon received a
match penalty for attempt to injure, resulting in his ejection from the game. Hollweg suffered a cut to the chin that required two stitches. According to
ESPN's
Barry Melrose, Hollweg escaped serious injury because Simon's blow caught his shoulder pads before hitting his face. 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. On March 11, he was suspended for the rest of the season, including playoffs, with a minimum of 25 games, and since the Islanders only played five playoff games, it continued into the first five games of the 2007–08 season. The
Nassau County district attorney considered filing criminal charges against Simon, but declined. Hollweg later told
Newsday that he was not interested in pressing charges.
Jarkko Ruutu incident 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. Simon skated in behind Ruutu and pulled Ruutu's leg back with his own. When Ruutu fell to his knees, Simon stomped on the back of Ruutu's right leg with his skate and then stepped into the bench area. 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. However, the next day, Simon was suspended without pay for 30 games, the third-longest suspension for an on-ice incident in modern NHL history behind a 41-game suspension to
Raffi Torres in
2015 and a one-year suspension handed down to
Marty McSorley in
2000 (though McSorley only sat out 23 games before his contract expired and he left the NHL). 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. Following the suspension, Simon returned to play one more game with the New York Islanders before being traded to the Minnesota Wild. 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. On March 15, 2008, after a second review, the NHL suspended Pronger for eight games.
Minor incidents 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. He played for three teams in the KHL, including Chekhov Vityaz (113 games from 2008-2011), Moscow Dynamo (9 games during the 2010-2011 season), and Novokuznetsk Metallurg (52 games from 2011-2013). In a total of 168 regular season games played, he attained 41 goals, 48 assists, 574 penalty minutes. He appeared once in the playoffs with Moscow Dynamo, playing six games, scoring two goals and earning 18 minutes of penalties. He retired from the KHL in 2013. ==Personal life and death==