Three different general managers in and around the Core Four era have tried everything at the NHL trade deadline, from swinging for the fences to singles and sacrifice bunts to get the Maple Leafs around the bases for a Stanley Cup.
But beyond successfully sliding into the second round two years ago, it has been too many strikeouts.
The window for Auston Matthews, Mitch Marner, William Nylander and John Tavares looked to be closing last spring after another Game 7 defeat to Boston … only to be propped open by promising developments this season.
Craig Berube arrived as head coach and forged a better defensive team, the highly criticized Marner not only stayed, but has played his way towards a new long-term contract and a possible first-place finish for the Leafs in the division could lead to a better playoff path. Nylander has soared, while Matthews has been hurt, with his best hockey to come.
Now it’s Brad Treliving’s plane to fly for a couple of days, up to Friday’s 3 p.m. EST finish line. Here’s what he and predecessors, Kyle Dubas and Lou Lamoriello, have attempted at this vital crossroads:
BRAD TRELIVING: Protecting the house
2024 — He moved to bulk up the defence with the acquisitions of Ilya Lyubushkin and Joel Edmundson (the latter had helped Montreal stun the Leafs during the first-round in 2021). Both blueliners played all seven playoff games against the Bruins, but the Leafs didn’t win and the duo didn’t stay.
Edmundson cost the Leafs a second-rounder to Washington. They also pried fourth-line winger Connor Dewar away from the Minnesota for a fourth-rounder next year. Dewar was injured much of this season, but can be a factor in the coming playoffs.
KYLE DUBAS: Too little, too late
2023 — In the boldest deadline offensive of his tenure, he brought back former first-round pick, defenceman Luke Schenn, a popular move that heralded Toronto’s first series triumph in 19 years. Dubas preferred his teams to be skill-based with “organic” toughness that would be developed within, though at each deadline he tried to bulk up.
But after the Panthers bounced the Leafs in the second round, Schenn couldn’t be enticed to remain long-term, leaving a hole that wasn’t filled full time until Jake McCabe (acquired a day before Schenn) and this year’s addition of Chris Tanev became permanent fixtures.
Dubas had earlier added St. Louis’ 2019 Cup winning forward Ryan O’Reilly, who did factor in beating Tampa in the opening round and had nine points in 11 playoff games. He, too, wasn’t interested in staying for what the Leafs offered. Hard-nosed winger Sam Lafferty also came with McCabe from Chicago, but was lost on waivers when the team misjudged rookie Fraser Minten’s NHL readiness at camp a few months later.
2022 — Warhorse defender Mark Giordano and bottom-six forward Colin Blackwell from Seattle came aboard for second- and third-round picks. Both played all seven games in the Lightning series that the Leafs lost in seven.
2021 — After a couple of years without a significant deadline move, heavy duty forward Nick Foligno was convinced to make an emotional departure from Columbus with the goal of emulating his father Mike’s playoff success in Toronto 20 years before.
It cost Dubas a first-rounder, the Jackets choosing defenceman Corson Culemans, who is still developing in the AHL, while an injured Foligno was not a factor in four games as Toronto was upset by Montreal.
2019 — Jake Muzzin doesn’t really qualify as a deadline pickup as he came in late January, but it was with the playoffs in mind that the grizzly defenceman was brought in from the champion Los Angeles Kings.
The bigger story that spring became outgoing coach Mike Babcock’s failed relationship with the younger Leafs, though Muzzin would stay and the first-rounder taken by L.A. was not exploited, becoming journeyman defenceman Tomas Bjornfot.
LOU LAMORIELLO: Playing it cool
2018 — It took a lot of getting used to, Tomas Plekanec’s turtleneck in Toronto colours instead of rival Montreal. Lou hoped his familiarity playing Boston would help in that year’s series, the first of two straight the Leafs would lose in seven to the B’s. Plekanec had four points, while the second-rounder to land him became Jacob Olofsson, a Swedish forward who elected not to sign in Montreal.
2017 — An exciting time, the club’s first post-season appearance in four years and Lamoriello decided the young guns deserved a boost for their months of hard work, in the person of Lightning power forward Brian Boyle. He’d managed a career-high five goals in the previous playoffs, but was held to two assists in a six-game, low-scoring loss to the Washington Capitals.
Again, the Leafs weren’t burned by surrendering a second-round pick, left winger Alexander Volkov playing far more KHL than NHL games.
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