TORONTO — Brendan Shanahan was still a few months from being hired as team president the last time the Toronto Maple Leafs defeated the Montreal Canadiens.
The Leafs losing streak against the Habs hit 13 games (0-9-4) at the Air Canada Centre on Saturday night, lingering now for almost three years following the 5-3 decision.
Toronto last defeated its original-six rival on Jan. 18, 2014, a point when the organization had yet to undergo the major reconstruction which would begin with Shanahan's hiring and continue with the additions of head coach Mike Babcock, general manager Lou Lamoriello and a completely overhauled roster built around skilled youth.
Only six players remain from the last Leafs squad to top the Habs (five who played that night), including James van Riemsdyk, who scored in that 5-3 victory three years back and again in the most recent defeat, which also ended Toronto's seven-game point streak.
"They've got a pretty strong team and it's a rivalry game and for whatever reason, yeah it just seems to be going their way lately," van Riemsdyk said after the loss, which saw Carey Price shine with 33 saves for Montreal.
Other than van Riemsdyk, the only players still left with the Leafs are Tyler Bozak, Nazem Kadri, Jake Gardiner, Leo Komarov and Morgan Rielly.
Most of the organization has been turned over since then, much of that new talent on display against the Canadiens, including rookie Mitch Marner, who posted his third three assist-outing already this season.
Toronto's failing in the latest loss began with a wobbly start, one that saw the Canadiens strike twice in the opening four minutes, including Max Pacioretty's 19th this year (and fourth in the last three games) along with a shaky second goal from Artturi Lehkonen which snuck under Frederik Andersen's right arm.
The Leafs erased the two-goal deficit by scoring on consecutive power plays.
Bozak got the first on a fabulous set up by Marner, the Toronto area product dropping a no-look pass to his senior teammate as he slid through the slot. Kadri added the second late in the period, his third straight game with a goal and sixth in the past nine outings.
The Leafs couldn't make it into the intermission at par though, Habs rookie Nikita Scherbak scoring his first NHL goal in his first NHL game with 0.9 seconds left in the opening 20 minutes. A 21-year-old former first-round pick (2014), Scherbak was recalled after Brendan Gallagher broke his hand, the latest in a long line of Montreal injuries which currently includes Alex Galchenyuk, Andrei Markov, Andrew Shaw and David Desharnais.
"You've got to know the time on the clock, you can't give up that goal at the end," Babcock said.
The Habs would score again 36 seconds into the second frame, Alex Radulov potting the power-play marker.
Van Riemsdyk would bring the Leafs back to within one on another tremendous play by Marner. With puck in tow, the 19-year-old whirled through the entire Montreal zone before dishing off to van Riemsdyk on the door-step, the American winger promptly tapping in his 14th goal this year.
It was Marner's third assist on the night and 32nd point in 39 games this season. He trails only teammate Auston Matthews (35 points) and Winnipeg's Patrik Laine (37) in the NHL rookie scoring race.
"I think it's the guys I play with," said Marner, who leads the Leafs with 22 assists. "They get open for me and give me the puck and find space for me."
Michael McCarron drove the Habs' lead back to two in the opening minutes of the third, his shot from just above the goal line beating Andersen, who struggled to the tune of five goals on 31 shots.
Babcock said he thought the game was over after that fifth marker against Andersen, who was starting on consecutive nights for the third time season. He's yielded four goals or more in dropping two of those three outings.
"Now we still pushed and had lots of chances, but I thought the fifth one killed us for sure," Babcock said, the Leafs beginning their five-day bye week on Sunday.
Price shined in stopping 25-of-26 shots over the final two periods. He was bowled over at one point by Leafs rookie Zach Hyman, the hard drive to the net eliciting fiery reactions from Shea Weber and the Canadiens along with a two-minute penalty.
"I think the league's got to make sure that they protect the goalie," Habs coach Michel Therrien said after his 400th career win. "You can't let guys run the goalie like that."
Price was in the net the last time Toronto beat Montreal, opposed by Jonathan Bernier, who got the upper hand with 30 saves.
Beyond van Riemsdyk, the Leafs other goal-scorers that day included Phil Kessel, Cody Franson, Mason Raymond and Joffrey Lupul, all of whom are no longer with the team.