Brendan Shanahan and the secret Olympic letter he wrote to himself

Team Canada's Brendan Shanahan celebrates with his gold medal after winning against the USA in the mens hockey final at the XIX Olympic Winter Games in West Valley City, Utah,Sunday Feb 24, 2002. (Tom Hanson / CP)

It’s 1998.

Brendan Shanahan is sitting on the bench in Japan listening to Team Canada coach Marc Crawford and his staff call out future Hall of Fame names to take part in a shootout that could get his country past the Czech Republic and into the Olympic gold medal game.

As the names ring out, "Fleury, Bourque, Nieuwendyk, Lindros…" Shanahan says to himself, "Pick me. Pick me. Pick me."

“All I’m thinking is, oh, my God, I hope I get to shoot. I hope I get to score the winner and be the hero,” Shanahan recalled Monday on the SmartLess podcast.

“And the fifth name, they go, ‘Shanahan.’ ”

Robert Reichel beats Canada’s Patrick Roy on the Czechs’ first attempt, then no one else scores. Shanahan, the final shooter, is his country’s last hope to solve Dominik Hasek.

“And I don’t score. I let down the whole country. It was very confusing to me,” said Shanahan, who’d always believed that the great ones are supposed to want the puck on their stick with stakes the highest.

Shanahan was already a veteran at that point, unsure if he’d even be able to crack the national roster at the next Winter Games, 2002 in Salt Lake City. He’d be 33 by then.

After much soul searching, and without even telling his wife, Shanahan wrote a letter to himself, "You’re going to make the Olympic team in 2002. You’re going to win the gold medal. You’re going to score the game-winning goal." He sealed the letter in an envelope, licked a stamp on it, mailed it to himself and stuffed it in a drawer for proof.

Four years later, he didn’t score the golden goal, but he most certainly became an Olympic champion. Only then did he root through the drawer and hand the letter, postmarked 1998, to his wife.

This is just one of several insightful little moments from the Triple Gold Club member and Toronto Maple Leafs president’s appearance on SmartLess, in conversation with close friend Will Arnett and actors Jason Bateman and Sean Hayes.

Over the 50-minute interview — a must-listen for fans — Shanahan touches on a range of topics, from his thoughts on Jerry Krause’s management style to his opinions on fighting, from his encyclopedic knowledge of popular movies to whether he’d consider becoming a coach (“Quite frankly, they make more money,” he quips).

In recounting his first meetings with Bateman and Arnett, the executive gives us a hilarious peek behind the curtain.

So close have Shanahan and Leafs fanatic Arnett grown that when Shanahan first accepted the Toronto job in 2014, he informed only two people outside of his home about the top-secret news.

“I’m going to tell the two people it means the most to. I’m going to call my mom, and I’m going to call Will Arnett,” Shanahan said.

“I texted Will: ‘Hey, man, I’ve just been named president of the Toronto Maple Leafs.’ He texted me back: ‘We did it.’

“I really just want to win here for people like Will.”

Do yourself a favour and listen to the whole episode here.

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