Defenceman Ted Green of the Boston Bruins struggles to his feet after being struck over the head during a stick-swinging duel with Wayne Maki of the St. Louis Blues during an exhibition hockey game in Ottawa Sept. 22, 1969. (Canadian Press)

The NHL handed out its stiffest punishment ever Wednesday, slapping Chris Simon with a 30-game suspension for stepping on Pittsburgh Penguins super pest Jarkko Ruutu during a game last Saturday. It isn't the first time Simon had run afoul the league's disciplinarians. The noted tough guy missed the first five games of this season while completing a 25-game ban handed out in March.

Simon's latest infraction is just the latest in a long line of violent incidents that have tarnished the game's reputation. Steve Downie and Jesse Boulerice both dealt the league black eyes earlier this season and the Todd Bertuzzi story just won't go away.

In light of the Simon incident, CBCSports.ca looks back at some of the most memorable acts of hockey goonery.

1. Retaliatory hit begets All-Star Game

Boston Bruins defenceman Eddie Shore was considered one of the roughest players of his era. On Dec. 12, 1933, in a game versus the Leafs, Toronto's King Clancy stood up Shore at the blue-line as he was rushing up the ice with the puck. No penalty was called.

An irate Shore exacted revenge by slamming into Leaf winger Ace Bailey with a vicious hit from behind, sending the future Hall of Famer crashing headlong into the ice.

Bailey suffered a fractured skull – onlookers said it sounded like a watermelon hitting pavement – and never played again. A benefit game held the next year in his honour morphed into what is now the NHL All-Star Game.

2. "Rocket" Richard's tomahawk & the ensuing riot

The longtime Hab set the standard for snipers with an eight-point game in 1944. Few can forget his 14 all-star selections or his 1961 Hall of Fame induction. But the fiery "Rocket" Richard may best be known for the riot he sparked.

It stemmed from a March 13, 1955, game in which Richard was given a match penalty for deliberately injuring Hal Laycoe - tomahawking him over the head with his stick – and punching linesman Cliff Thompson. Richard was later suspended for the rest of the season, causing an uproar amongst Habs fans, given Richard was leading the NHL in scoring and his team was battling for first place.

The following season, NHL president Clarence Campbell was pelted with eggs while attending a game between the Canadiens and Detroit at the Montreal Forum. The game was forfeited and the arena evacuated due to an out-of-control crowd that took to the streets. A riot ensued, causing $500,000 in damage.

3. Wayne Maki fractures Ted Green's skull

Imagine the worst stick-swinging incident of the modern NHL era, complete with heavy wooden sticks and helmets nowhere in sight.

Voila, you have St. Louis' Wayne Maki opposite "Terrible" Ted Green of the Boston Bruins, circa 1969-70 in Ottawa.

In the midst of a pre-season game, Maki knocked Green down from behind. The latter retaliated by slashing Maki, who hit the ice. Maki speared Green, who again sent Maki flying. The pair soon exchanged vicious slashes until Maki clubbed Green over the head, fracturing his skull.

Green needed three major operations to save his life and had a steel plate inserted in his head. Maki was suspended for 30 days and Green for 12 games when he returned to action one year later. Assault charges were filed against both players, who were later acquitted.

4. Bobby Clarke's Summit Series chop

While most incidents of on-ice violence are met with shock and disciplinary action, Bobby Clarke's slash on Soviet superstar Valeri Kharlamov's ankle has been lauded in some hockey circles as an act of heroism.

With Canada trailing in the legendary series 3-1-1 and mired in a dogfight in Game Six, Clarke, at the encouragement of assistant coach John Ferguson, delivered a brutal two-hand slash to Kharlamov's sore ankle. The attack proved to be the turning point in the emotionally-charged matchup.

Kharlamov, the Soviets' most skillful player, was never the same after the hack, and the Canadians rallied for a series victory. When asked about the incident years later Clarke said: "If I hadn't learned to lay on a two-hander once in a while, I'd never have left Flin Flon." The attack also cemented Canadian hockey players' reputation as thugs who won games through intimidation and violence rather than skill and finesse.

5. Maloney crowns Glennie; crown sticks it to Maloney

Dan Maloney's NHL resume includes a Stanley Cup appearance, all-star selection and three 20-plus goal seasons. Oh yeah, and an assault charge as well.

The former Detroit Red Wings left-winger was involved in an on-ice attack against Toronto's Brian Glennie on Nov. 5, 1975. Glennie's skull met Maloney's stick tomahawk-style, and it was lights-out for the Leaf. The incident made further headlines when Ontario crown attorney Roy McMurtry became involved and made the charge against Maloney.

Glennie was put on the stand, but it didn't matter much. "When I testified, I said very little," he joked later. "How could I? I was out cold at the time."

In exchange for a no-contest plea, Maloney did community service work. He also was banned from playing in Toronto for two seasons. Maloney finished his playing career with the Leafs in the early 1980s before embarking on a coaching career with the club.

6. The night the lights went out

There have been plenty of modern-day brawls in hockey, but none have come close to the impact of the 1987 world junior championship game in Czechoslovakia.

Canada was in contention for the gold medal and leading Russia 4-2 in the final game of the tournament … until a bench-clearing brawl erupted. The ice was covered in helmets and gloves, and pairs of skaters – goalies included – engaged in an orgy of rock-em sock-em blows.

When officials failed to get control of the melee, they shut off the lights at the arena. The players continued to fight in the dark, and organizers cancelled the game. Both teams were eventually disqualified.

Some Canadians were proud of the squad (Don Cherry, for one), while others were ashamed of the reputation it gave our national pastime.

7. Hunter ends Turgeon's playoff run

Dale Hunter could hurt an opposing team in several ways. The winger was never one to shy away from the dirty side of hockey. When he retired from the game in March 2000, he was the only player in NHL history to record more than 300 goals and 1,000 points while still recording over 3,000 penalty minutes.

But his brutal crosscheck on New York Islanders forward Pierre Turgeon in an April 1993 playoff game was a black mark on his career. After Turgeon scored a series-clinching goal, Hunter came in from behind and nailed the Islanders forward into the sideboards, separating Turgeon's shoulder. Hunter, then with the Washington Capitals, was given a then-NHL-record 21-game suspension. Turgeon missed six weeks of action and his Islanders exited the post-season during the conference finals.

8. Jeff Kugel runs wild in OHL game

It was like a scene straight out of World Wrestling Entertainment.

A junior-hockey enforcer leaves the bench to join a brawl, sucker-punches an opponent from behind, straightens his arms while standing over him, works the crowd, chases away another player already involved in a fight, works the crowd again and throws his arms wildly like a crazed lunatic, challenging players, fans and all comers.

On Nov. 2, 1998, Jeff Kugel was handed a 25-game suspension for attacking Juri Golicic, as well as a lifetime ban from the Ontario Hockey League as a result of the incident that occurred a month earlier between the Windsor Spitfires and the Owen Sound Platers.

OHL commissioner David Branch softened his hardline stance on Kugel's punishment following a lengthy appeal, saying the then-18-year-old could apply for reinstatement at the end of the season.

Windsor later waived the six-foot-seven-inch, 265-pound Kugel, who went on to play two games for the Sault Ste. Marie Greyhounds in 1999-2000 and four contests that same season with the Flint Generals of the United Hockey League.

9. The Bertuzzi Incident

Looking to exact some revenge against a rookie who less than month earlier had clocked his captain and superstar friend Markus Naslund, hulking Canucks' forward Todd Bertuzzi stalked a much smaller Steve Moore around the ice, attempting to goad him into a fight during the waning moments of a blowout in Vancouver. When the Colorado Avalanche forward refused to drop the gloves, Bertuzzi pounced from behind, punching Moore unconscious before the two players crashed to the ice.

The force of the impact left Moore with a fractured neck and a serious concussion. He hasn't played since. Branded a villain Bertuzzi was banned for the rest of the season and playoffs. A B.C. court found him guilty of assault, sentencing him to a year's probation and 80 hours of community service.

Bertuzzi has also struggled to get his career on track since. After a sub-par season and a poor Olympics, the Canucks traded the power-forward to the Florida Panthers in the summer of 2006. Hampered by a bad back Bertuzzi only played seven games for the Panthers before being shipped to the Detroit Red Wings in February.

10. The Marty McSorley trial

Perhaps no other incident resonated in and out of hockey circles than Marty McSorley-Donald Brashear affair of February 2000.

McSorley, in the dying seconds of a game between his Boston Bruins and Brashear's Vancouver Canucks, slashed the side of Brashear's head with his stick. When the blow was struck, Brashear fell backwards and slammed his head against the ice. Brashear, who had no memory of the incident, suffered a severe concussion.

Outrage ensued and McSorley, who was suspended for 23 games, found himself on trial for assault with a weapon that October. The aging enforcer, who could have received an 18-month jail sentence, was handed an 18-month conditional discharge. The only stipulation was that he couldn't play any sport where Brashear was on the opposing team.

However, that condition really didn't matter anyway. McSorley, a 17-year NHL enforcer with two Stanley Cups to his name, never played another NHL game.