For decades, the Toronto Maple Leafs have been one of the NHL's most valuable and visible franchises - yet one of its most consistently underachieving.
Despite boasting elite talent, deep financial resources, and a loyal fanbase starved for success, the organization has repeatedly squandered its assets through questionable trades, poor contract decisions, and inconsistent leadership.
While other teams rebuild, adapt, and rise, the Leafs remain stuck in a cycle of hype and heartbreak. Systemic mismanagement has held the team back, and is why, even in the era of Auston Matthews, a Stanley Cup feels out of reach.
The mishandling of assets is why current Maple Leafs general manager Brad Treliving and coach Craig Berube are scrambling to realign the roster in search of playoff success.
Leafs gambled and lost on Mitch Marner
Star winger Mitch Marner's departure via a sign-and-trade with the Vegas Golden Knights was botched by the Leafs. Marner was a first-round pick, 4th overall, by Toronto in 2015.
In his nine seasons with the Maple Leafs, he became the team's fifth all-time leading scorer with 741 points. Marner is an over-a-point-per-game player who plays in all situations.
The Leafs return for the sign-and-trade was Nicolas Roy, a checking line center with 166 career points (a season and a half for Marner). It's better than Marner leaving for nothing, but a severe squandering of an asset nonetheless.
Treliving deserves some latitude for his handling of Marner. The player and his agent were determined to reach free agency, and Treliving made attempts to move Marner for a much more valuable piece (Mikko Rantanen), but was denied by the no-movement clause in Marner's contract.
Team success did not happen during Marner's time in Toronto, so change was necessary for both him and the Leafs.
Wisely, Treliving has not spent foolishly on a poor free agent class to replace Marner. He has traded for Matias Maccelli and Dakota Joshua, but neither is in Marner's class.
With a mouth-watering UFA class of 2026, the grade for Marner's exit is incomplete. Should some of the Maple Leafs' salary cap space be allocated for an impact player next summer, his leaving becomes more palatable; however, as of now, it's a major loss.
Nazem Kadri was never replaced
Treliving was not at fault for two other roster catastrophes with the Maple Leafs. Nazem Kadri was the Maple Leafs' first-round pick, 7th overall, in 2009.
The talented, feisty center has made a career of playing on the edge. His inability to harness that aggressiveness resulted in two playoff suspensions that potentially cost the Leafs series victories in back-to-back years against the Boston Bruins.
Instead of being patient, Toronto traded him and defenseman Calle Rosen to the Colorado Avalanche for Alex Kerfoot, Tyson Barrie, plus an exchange of draft picks. In 2022, Kadri helped the Avalanche win the Stanley Cup.
Kadri then signed a free-agent deal with the Calgary Flames and has played some of his best hockey during his years there, well into his thirties. With the Leafs' desire for a top-six forward, much of the team's fanbase is longing for his return.
Kerfoot had a few serviceable seasons in Toronto, but moved to the Utah Mammoth as an unrestricted free agent. Barrie played one season with the Leafs before also moving on as a UFA.
Joe Miller, taken with the 6th round pick in the Kadri trade with the Avalanche, is the lone remaining piece from that trade still with the Maple Leafs. He played with Harvard University in 2024-2025 and is not a top prospect.
2021 free agency: A massive failure for Leafs
In the summer of 2021, the Maple Leafs let Zach Hyman walk in free agency. He signed for seven years with the Edmonton Oilers at a $5.5 million AAV.
Hyman has gone on to score 27, 36, 54, and 27 goals in his first four seasons in Edmonton, playing over seventy games each year. He has helped the Oilers reach the Stanley Cup final twice.
While watching Hyman go elsewhere, the Leafs signed players such as Nick Ritchie, Ondrej Kase, Michael Bunting, and David Kampf, who they are now trying to trade away.
Bunting had a couple of good seasons in Toronto, but left as a UFA due to the Leafs' cap constraints. Toronto did not sign any notable free agents in 2022 to help offset Hyman's leaving.
Hyman is a tenacious player with dogged determination. Like Kadri, Hyman is the type of player Treliving and the Maple Leafs are in search of in their quest for a DNA change. Like Kadri, the Leafs had him but let him go.
Three major assets for a checking-line center and a long-shot sixth-round draft pick. That's how the Toronto Maple Leafs keep wasting talent in search of elusive success.