By Tyler Paterson

Hockey is a sport for the true man’s man. With near constant, high speed action, no place to go out of bounds and stop a play, and a rule that actually allows players to fist fight, it is one of the most exciting sports to watch.

The fighting rule, while still controversial, is often argued that is makes the game SAFER! Not every player wants to brawl. Some make skating and scoring look damn near poetic! But heaven forbid someone throws a cheap shot on them, or career ending blindsided hit. If the ref missed it, or even caught it, that player would then have to answer to that team’s resident tough guy enforcer. This is something most players would never want to do, and thus the cheap shots are kept to a bare minimum. These are 5 of the scariest enforcer’s you would never want to meet in a dark alley…or a well-lit arena surrounded by screaming fans.

1) Chris Nilan

While spending most of his career as part of the Montreal Canadiens, Nilan soon donned the moniker “Knuckles” for his tough guy mentality. Always one to stand up for his team, never one to back down from a fight, Chris Nilan didn’t care if he had teeth knocked out during a scrap. Not only did he accrue over 3,000 penalty minutes during his career (one of only 9 NHL players to ever do so), but he changed the game after getting ejected from the ice and picking a fight with the entire Bruins bench. The NHL decided to create a glass partition separating those ejected from the opposing team, which became known as the Nilan glass. Doesn’t get much more badass than that!

Check out his heart and toughness here.

2) Marty McSorley

Many sports writers agree that part of the reason Wayne Gretzky achieved such great heights is because of his good friend Marty McSorely. If anyone even touched Gretzky, even just looked at him wrong, McSorely was there to throw down, and boy was he scary. Nothing would stop his buddy Wayne from achieving the potential he would eventually live up to, and through his career he had some legendary bare knuckle dance partners. Unfortunately, his incident with Donald Brashear went down as one of hockey’s most infamous ugly hits. He was suspended 23 games after using his stick like a baseball bat and cracking Brashear in the head. For a tough guy that should be preventing cheap shots, this was the ultimate betrayal. Still, he was one scary dude.

3) Terry O’Reilly

Widely considered one of the most effective hockey enforcers of all time, Terry O’Reilly played for the Big Bad Bruins as a monster on the ice. Never one to shy away from trouble, he racked up over 200 minutes of penalty time in five consecutive seasons and earned both the monikers “Bloody O’Reilly” for his aggressive fearless style, and “Taz” after the Looney Tunes character for his wildman attitude. During a game with the New York Rangers, O’Reilly actually jumped the glass and attacked a fan who was leaning over and taking swings at Bruins with a tightly rolled program. When his number was retired next to Ray Borque’s, Borque was quoted to say that his banner “hangs next to mine, protecting me again.”

Check out Bloody O’Reilly’s greatest hits here.

4) Bob Probert

Perhaps the scariest enforcer to ever play, Bob Probert was infamous for his tenure with the Detroit Red Wings. This was a guy who was known for his antics both on and off the ice, never willing to give an inch and always press forward. Legal troubles aside, Probert and his buddy Joey Kocur became known as the ‘Bruise Brothers’ for their drop of the hat, fly off the handle attitude when it came to sticking up for their team. Due to his size, strength, and power, many fans referred to the enforcer as the Muhammad Ali of hockey. And for good reason! Taking on all challengers, he was both feared and revered.

It’s not hard to understand why after watching some of his clips.

5) Derek Boogaard

With a nickname like “The Boogeyman,” the thought of this guy coming after you was a scary, scary thought. In 2007, he was voted the second most intimidating player to play in the NHL, just behind Georges Laraque. Laraque later attributed his retirement in part as an avoidance of conflict with Boogaard after the Boogeyman pounded Todd Fedoruk so badly that Fedoruk had to have a metal plate inserted to repair his cheek. Standing at a massive 6’7 (without skates!) and weighing in at 270 pounds, he towered over other players. Boogaard was known for his one-punch knockouts, nose breaks, cringe-inducing uppercuts, and checking people THROUGH the glass partitions. He was so scary, that players on opposing teams often came down with mystery flu’s the night before games, which many believed was just a way to avoid having to deal with Boogaard. Unfortunately, Derek Boogaard lost his life at the young age of 28, but his legacy lives on through the brutality and excitement he gave to the sport.


Tyler Paterson was born and raised in Boston and is a fan of the Red Sox, Bruins, and Patriots. He’s also an avid MMA fan and can recall UFC events, dates and fighters on demand. In his free time, Tyler tours the country with his comedy band.