Jon Greenwood coached NHL star Nathan MacKinnon back in Peewee and Bantam. He says he knew then that a successful career in hockey was possible for the young phenom.

“We knew we had a really special talent," said Greenwood. “He was a special worker.”

A first overall NHL draft pick and a Memorial Cup champion in 2013, MacKinnon now has a chance to win his first Stanley Cup Friday night with the Colorado Avalanche.

“It is certainly another box to check in a remarkable career so far," said Greenwood.

Joe DiPenta knows what it's like to experience a career defining moment like the one facing MacKinnon. The Cole Harbour native won a Stanley Cup with Anaheim in 2007.

“Usually when I go back and watch the video, it seems like 30 seconds but it was only six seconds," DiPenta said as he recalled hoisting the Stanley Cup.

“Nathan is probably very nervous and he’s probably thinking 'wow, this is the biggest game I have ever played in and I have the opportunity to do something that’s going to change my life forever.’”

Ryan Falkenham played with MacKinnon from first-year Novice, all the way to Major Junior.

“He doesn’t stop, whether it’s practice or training and he’s always had that drive that is unparalleled," said Falkenham.

As DiPenta continues to watch the playoffs, he said it seems the closer MacKinnon gets to winning his first NHL championship, the harder he seems to work each night.

“He gets a puck and he’s on a mission," said DiPenta.

That mission to win the Stanley Cup is nearly complete for MacKinnon.