Since Auston Matthews burst onto the scene in 2016, the Toronto Maple Leafs have experienced the highs of regular-season accolades and the heartbreaks of numerous postseason failures.
While the team has built a core of elite talent, it has also parted ways with several players - through trades, free agency, or roster management - who have gone on to thrive elsewhere. In hindsight, some of the departures look far more painful than they did at the time.
Leafs' general manager Brad Treliving and coach Craig Berube have shifted the team's style since their arrival and continue to mold the roster to their liking. This summer's loss of long-time key player Mitch Marner has ignited discussion of a reunion with a player the Maple Leafs once had in their stable. Letting that player go was one of Toronto's lamentable decisions over the past decade.
As the quest to replace Marner plods along, it's a good time to look back at the most regrettable player losses of the Matthews era - moves that Leafs fans still question, and in some cases, wish could be undone.
Honorable Mention: September 2015 -- Trade of Carter Verhaeghe
Carter Verhaeghe was picked in the third round, 82nd overall, by the Maple Leafs during the 2013 NHL entry draft. He didn't play a game with the Leafs before being included as a throw-in as part of a five-for-one trade to acquire speedster Michael Grabner from the New York Islanders.
Grabner played one forgettable season in Toronto, scoring nine goals in 80 games. It took a few years, but after the Islanders traded Verhaeghe to the Tampa Bay Lightning, he made his NHL debut in 2019-2020.
Verhaeghe parlayed that season in Tampa Bay into a free-agent contract with the Florida Panthers. He has since signed two subsequent deals to extend his stay with the Panthers, the latest a maximum eight-year contract that runs to 2033.
The center has four consecutive seasons of scoring twenty-plus goals, with a career-high of 42. The trade of Verhaeghe happened before the arrival of Matthews, but it has to pain the Maple Leafs seeing the clutch playoff performer across the ice as an important contributor for their division rival in making three successive trips to the Stanley Cup Final, winning the last two.
3. February 2020 -- Mason Marchment traded for Denis Malgin
Mason Marchment played four games for the Maple Leafs during the 2019-2020 season. He was considered expendable by Toronto's previous general manager Kyle Dubas and was sent to Florida for the smaller, thought to more skilled, Malgin.
Malgin never found his niche in Toronto or the rest of the NHL, and is now playing in Europe. Marchment blossomed during his second year with the Panthers, scoring 18 goals with 47 points in 54 games.
Marchment moved to the Dallas Stars in free agency, became a consistent twenty-goal scorer with some bite, and was just traded to the Seattle Kraken at the start of the offseason.
2. July 2021 -- Zach Hyman signs with the Edmonton Oilers
It was well-known approaching NHL Free Agency in the summer of 2021 that Zach Hyman was likely signing elsewhere. The Maple Leafs had too much of their cap space tied up by contracts to Matthews, Marner, John Tavares, and William Nylander.
The commitment to the Core 4 cost the team Hyman. The winger was loved in Toronto by his coaches, teammates, and the fans for his relentless, hardworking style.
At the time, it was understandable that the Leafs had reservations about paying a high salary - $5.5 million AAV - over a long term, seven years, for a player whose style might result in injury and was aging.
Hyman, however, has taken off in Edmonton. He has played over seventy games in each of his four years with the Oilers, scoring 27, 36, 54, and 27 goals.
The former Leaf plays in all situations and has a tenacity and work ethic that all teams covet. With the NHL salary cap rising, his $5.5 million AAV is now a bargain.
1. July 2019 -- Nazem Kadri traded to the Colorado Avalanche
This trade is looking worse as time passes. Kadri was taken by the Leafs with the 7th overall pick in the 2009 NHL Entry Draft. It took a few seasons for him to get comfortable and perform at the NHL level, but Kadri excited Maple Leafs fans with his highlight-reel goals and penchant for nastiness on the ice.
That feistiness led to his demise with the Maple Leafs. His controversial playoff suspensions in back-to-back seasons, for boarding the Boston Bruins' Tommy Wingels in 2018 and for a dangerous crosscheck to the head of Jake DeBrusk in 2019, resulted in the Leafs trading him to the Colorado Avalanche.
Ignoring the exchange of low-round draft picks, coming to the Leafs were Alex Kerfoot and Tyson Barrie. Kerfoot was a serviceable forward for a few years, but lacked a significant impact. Barrie played one season with Toronto before bouncing around the league for the next few years.
Kadri lacked maturity at times during his years in Toronto and needed to be properly harnessed. Despite his playoff indiscretions that potentially cost the Maple Leafs series victories against the Bruins, his playing style is suited for the playoffs.
The veteran center helped the Avalanche win the Stanley Cup in 2022. Most of his productive and best seasons have happened since he left the Leafs.
Kadri is the type of player that the Toronto Maple Leafs are currently yearning for. It makes Treliving, Berube, and Leafs fans wish he never left in the first place.