However, the Skateboarding Hall of Famer was humbled and outmatched when he faced off against a Canadian pro hockey enforcer named Kip Brennan.
Mike V didn't know that an enforcer's job is to deter and respond to dirty or violent play by the opposition. When such play occurs, the enforcer is expected to respond aggressively by fighting or checking the offender.
The clash, pitting a street-skating icon against a professional athlete on the ice, became an unforgettable moment in skateboarding history.
It all began when Mike V challenged Brennan, who wanted to test his mettle.
Vallely, no stranger to physical confrontation in his skateboarding career, challenges Brennan without hesitation. Little did he know he was about to enter an entirely different arena.
It became evident that Mike V was in for a humbling experience as he snapped his finger in the first round.
The pro hockey player demonstrated superior fight game, and Vallely found himself repeatedly outmaneuvered.
Fans who had seen him take on multiple opponents couldn't help but watch in disbelief as the skateboarding legend struggled to keep his footing on the ice.
Stream "Mike V's Greatest Hits Video" below at 30.17 to watch the fight, and don't forget to share it with your friends on social media. Enjoy!