Sometimes, when two unevenly matched teams face off, it’s the underdog who secretly holds the upper hand.

“The most nervous guy in the playoffs is Barry Trotz,” said Don Cherry, who joined The Andrew Walker Show on Sportsnet 590 The Fan, along with Ron MacLean, to talk about the upcoming Stanley Cup Playoffs—and in particular, the Washington Capitals’ series versus the Toronto Maple Leafs.

According to Cherry, Trotz has reason to be nervous because a first-place team facing a lowly underdog faces pressures to prove its might.

“All Toronto has to do is win one game and the whole season’s wiped out,” he said.

If the Capitals are haunted by the ghosts of playoffs past, it’s in part because of experiences like their first-round matchup with the Montreal Canadiens back in 2010. Montreal, the eighth seed, came away victorious thanks in large part to goaltender Jaroslav Halak standing on his head.

As the Capitals prepare to take on the Leafs, Cherry thinks Toronto goaltender Frederik Andersen could be a difference-maker.

“That Andersen, he’s capable of turning into Halak,” Cherry said.

“It all depends on the goalies,” he added. “You’ve got a good goalie, the goalies are hot, you win. That’s the whole thing.”

That’s not to say that the Leafs are all that likely to escape their first-round matchup with the Capitals, though. But they’ll be facing lower expectations than the Presidents’ Trophy winners.

“Talk about guys cutting it fine,” Cherry said of the Leafs earning a playoff berth in their penultimate game of the regular season.

“That was some game, I’ll tell you,” he continued. “You’ll never get in the playoffs [with a] better game than that.”

The Leafs’ odds of defeating the Capitals might not be great, but which of the five Canadian teams is most likely to make it past the first round?

“I would say Ottawa,” Cherry remarked. MacLean, though, is betting on the Edmonton Oilers. “I think San Jose looks like they’re a little banged up,” he said.

Cherry was less certain, because the Sharks are still a fearsome team. Whatever happens, it’ll be must-watch hockey. “Boy, that’s gonna be a war out there,” Cherry said.