2000 started with the late, Pat Quinn, having both the coach and GM title. Quinn would go on to hold his role as GM until the 2003 season, winning one division title, and making four appearances in the Stanley Cup Playoffs. After Quinn was fired in 2003, John Ferguson Jr. took over for close to five years, followed by Cliff Fletcher replacing JFJ in 2008, only to hold the role from January to November that year.

Fletcher would be let go in 2008, with the polarizing Brian Burke taking over, holding the position for four and a half years. Burkie missed the playoffs every year and was eventually replaced by his right-hand man, Dave Nonis, who was GM of the Leafs from Jan 9, 2013 – Apr 12, 2015. From Nonis, it was Lou Lamoriello’s turn, as ‘Robidas Island’ was created, and some interesting moves followed during Lamoriello’s, close to three-year tenure.

Lamoriello departed Apr 30, 2018, with youngster Kyle Dubas famously taking over on May 11, 2018. Dubas made a ton of bold moves and wasn’t afraid to spend assets on players he’s familiar with. Dubas won one division title and his teams made five Stanley Cup Playoff appearances before a contract dispute turned ugly, and perhaps some miscommunication was a big factor in president Brendan Shanahan walking away from extending Dubas, ending his tenure as Leafs’ GM on May 19, 2023.

Brad Treliving has taken over since, and while Treliving has made a couple of head-scratching trades the past year and a half, nothing compares to these five worst Maple Leafs trades of the last quarter-century:

Maple Leafs trade rights to Tuukka Rask to the Boston Bruins for goaltender Andrew Raycroft

June 24, 2006, perhaps the worst trade in Maple Leafs’ history. JFJ decided he wanted a goaltender who was NHL-ready, moving Rask, a 2005 21st-overall pick, to the Bruins, for Raycroft. Yes, Raycroft had won the Calder Trophy as the league’s best rookie in 2004, but his game fell off considerably in his second season, posting an 8-19-2 record, with a .879 save percentage prior to the deal.

Meanwhile, Rask was one of the best goaltender prospects outside of the NHL. In his first season playing pro in North America, he posted an impressive 27-13-2 record in the AHL, with a 2.33 goals-against average. The rest is history. Rask would go on to help the Bruins win a Stanley Cup in 2011. He ended his NHL career with an impressive 308-165-66 record and a Vezina trophy as the league’s best goaltender in 2014.

Raycroft dressed in just 91 games for the Leafs over the span of two seasons and managed to appear in 280 career NHL games. Raycroft sits second all-time in Maple Leafs history with 37 wins in a season, a record Frederik Andersen broke during the 2017-18 season.

Maple Leafs acquire Nick Foligno from Blue Jackets for ’21 first-round, & ’22 fourth-round pick

This trade also included the Leafs sending a 2021 fourth-round pick to the San Jose Sharks for minor-league forward Stefan Noesen. However you slice it, Dubas swung and missed in a major way.

Foligno had to deal with COVID-19 restrictions and had to isolate from his teammates back home in Sudbury, ON and wasn’t able to find any chemistry on the ice, or good health for that matter. Foligno hurt his back and wound up only appearing in seven regular season games for the Leafs, and also four Stanley Cup Playoff games. He wasn’t able to produce, recording just five assists in the 11 combined games in blue and white.

Essentially, three draft picks, including a first-rounder for 11 games. It was a trade that set the Leafs back, there’s no doubt about it, and it’s one that had a ton of influence on Dubas’ future in Toronto.

Maple Leafs ship Nazem Kadri, Calle Rosen, ’20 third-round pick to the Colorado Avalanche for Tyson Barrie, Alex Kerfoot, ’20 sixth-round pick

Speaking of Dubas’ swinging and missing, the Nazem Kadri likely takes the cake. On July 1, 2019, the first day of free agency, the then-Leafs GM decided to move Kadri to the Avalanche for a two-way blueliner in Barrie, and a depth forward in Kerfoot.

Kadri had been suspended twice during the postseason, so yes, that factored into the decision, but there’s no doubt the Leafs could still use Kadri in their lineup to this day. Isn’t it ironic, that all the reports these days circling Leafs’ trade talk are around looking for a middle-six centre?

Kadri went on to win the 2022 Stanley Cup with the Avs, and spent three seasons in Colorado, including a career year, posting 87 points in 71 games during the Cup-winning season. He’d also register 15 points in 16 postseason games during the Cup run and was a major part of Colorado’s championship season.

Meanwhile, Barrie lasted one season in Toronto, posting 39 points in 70 regular season games, and zero points in five Stanley Cup Playoff games. He’d leave for a one-year deal with the Edmonton Oilers the very next summer, while Kerfoot was a solid depth piece for the Leafs for parts of four seasons. The Maple Leafs still miss Kadri to this day.

Maple Leafs trade Adam Mair & ’01 second-round pick to L.A Kings for Aki Berg

This turned out to be a horrible trade for the Maple Leafs, as Quinn was just trying to make his blueline tougher to play against, however, the Kings cashed in on the second-rounder in a major way.

The 6-foot-3 Berg would go on to play parts of five seasons with the Maple Leafs, before retiring from NHL hockey. He quickly became the ‘whipping’ boy for Leafs Nation, and after having some serious potential as a former third-overall pick, didn’t materialize into a top-four NHL defenceman.

Meanwhile, Mair would go on to play 10 more NHL seasons, becoming a reliable depth forward, who brought some sandpaper to the lineup. However, the kicker here was the second rounder, which the Kings used to select Richmond Hill, ON native Mike Cammalleri. Yes, the same Cammalleri who dressed in 906 career NHL games, scoring 294 goals, and 642 points.

Maple Leafs trade Carlo Colaiacovo and Alex Steen to the St. Louis Blues for Lee Stempniak

We saved the best of the worst for last. Two former first-round picks, Colaiacovo and Steen were dealt in a two-for-one swap with the Blues, which was an absolutely horrible move by Fletcher, who was replaced less than a week later.

Stempniak lasted just two seasons in Toronto, meanwhile, Steen and Colaiacovo turned into key pieces for the Blues moving forward, more so Steen, who dressed for 12 seasons with the franchise, winning a Stanley Cup in 2019.

Imagine moving two former first-round picks for a forward who posted 38 points in 80 games the season prior. Likely one of the many factors as to why the Leafs decided to replace Fletcher shortly after this trade was finalized.

Honourable mentions:

Mar. 5, 2003: Maple Leafs acquire Owen Nolan from the Sharks for Brad Boyes, Alyn McCauley and ’03 first-round pick (Mark Stuart)

Mar.4, 2009: Maple Leafs trade Nik Antropov to the Rangers for ’09 second-round pick (Kenny Ryan), and ’10 fourth-round pick

Feb.27, 2007: Maple Leafs trade Brendan Bell, ’08 second-round pick (Roman Josi), to Coyotes for Yanic Perreault and ’08 fifth-round pick

Jun.24, 2011: Maple Leafs trade picks #30 and #39, to the Ducks for pick #22. Toronto selected Tyler Biggs, Anaheim selected Rickard Rakell and John Gibson.

Feb.19, 2020: Maple Leafs trade Mason Marchment to the Panthers for Denis Malgin

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