The Toronto Maple Leafs team of the early 2000s was one of the most beloved by Leafs Nation. With names like Mats Sundin, Gary Roberts, Darcy Tucker, Bryan McCabe, Alexander Mogilny and many more, the roster resonated with fans. Once known as the Beasts of the East, they had the best chance to make the playoffs and win the Stanley Cup.

After the 2004-05 lockout, things got ugly for the Maple Leafs, and they dealt with constant disappointment. Before the 2016-17 season, they had missed the playoffs 10 times in 11 years. It wasn’t until 2014 that the draft and developing players became a priority. The Maple Leafs went into a full-blown rebuild where prospects and picks became essential to their success.

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Before that, the Maple Leafs had handed out picks like Halloween candy, cutting corners to try and speed up the process. As good as Phil Kessel was, giving up potential stars like Tyler Seguin and Dougie Hamilton didn’t sit well.

It’s always hard to predict if prospects will pan out, especially from the later rounds, but if the Maple Leafs had focused on prospects and development after the lockout, they would’ve been in a better spot. Instead, they were stuck in the past as other teams started to change their philosophy. Here are six trades involving draft picks made by the Maple Leafs where the other teams struck gold. 

The Brian Leech Trade

To Maple Leafs: Brian Leetch, 2004 conditional fourth-round draft pick (Roman Kukemburg, 113th overall)
To New York Rangers: Jarkko Immonen, Maxim Kondratiev, 2004 first-round pick (Kris Chucko, 24th overall), 2005 second-round pick (Michael Sauer, 40^th overall)

This trade seemed good at the time to get Leetch. The Maple Leafs wanted a strong defender with playoff experience to make a deep playoff run. However, he was aging and his next season with the Boston Bruins would be his last in the NHL.

Immonen and Kondratiev saw limited NHL action, while Kukemburg saw nothing. Furthermore, Kukemburg could have been Ryan Callahan, who the Rangers took with the 127^th overall pick. Callahan played 757 games with the Rangers and Tampa Bay Lightning and Toronto could have had a great depth forward who plays with an edge. 

The Rangers’ first-round pick was eventually traded to the Calgary Flames to swap picks at the 2004 Draft. The Rangers selected Lauri Korpikoski 19^th overall who was a good depth player, while the Flames selected Kris Chucko who played only two games in the NHL.

While the players near the end of the first round weren’t appealing, if the Maple Leafs had kept this pick, they could’ve had defenseman Mike Green (29th overall by the Washington Capitals) who had back-to-back 70-point seasons in 2008-09 and 2009-10.

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The second-round pick in 2005 didn’t seem promising. However, Paul Stastny could’ve been selected, as he was still on the board four spots after Sauer was drafted by the Rangers. If the Maple Leafs had wanted to make a statement, Kris Letang was still on the board. A future three-time Stanley Cup winner, Letang would’ve bolstered Toronto’s blue line with a steady presence in both the offensive and defensive zone.

Defensemen To Be Had

To Maple Leafs: Ron Francis
To Carolina Hurricanes: 2005 fourth-round draft pick (Jared Boll, 101^st overall)

While few names have had successful careers who were selected in the later rounds of that draft, a few could have benefited the Maple Leafs. Jared Boll played in 579 games and racked up almost 1,300 minutes in penalty minutes. This was when enforcers still had a place in the game.

If the Maple Leafs had kept the pick and passed on Boll, they still could’ve had offensive defenseman Keith Yandle (taken 105^th overall by the then- Phoenix Coyotes) or future Stanley Cup winner Niklas Hjalmarsson (108^th overall by the Chicago Blackhawks).

Yandle would’ve provided strong offensive production for a defense that became an issue two or three years down the line. After his rookie year, Yandle’s point totals over the next few seasons were: 30, 41 and 59. He has always been a consistent point producer and would’ve been a good piece alongside Tomas Kaberle who was still producing at the time. Hjalmarsson would’ve provided a steady depth presence in a shutdown role, better than other players in the lineup like Jeff Finger.

Missing Out on a Norris Candidate

To Maple Leafs: Yanic Perreault, 2008 fifth-round pick (Joel Champagne, 129th overall) 
To Phoenix Coyotes: Brendan Bell, 2008 second-round pick (Roman Josi, 38^th overall)

Around this time is when the moves started to kill the Maple Leafs’ draft selection and adding to their prospect pool. At a time when playoffs were becoming less of a reality, they could’ve used as many picks as possible to draft and develop quality talent. 

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The Maple Leafs selected Joel Champagne who saw no NHL games when they could’ve had Jared Spurgeon (selected 156^th overall by the NY Islanders) or Cam Atkinson (selected 157^th overall by the Columbus Blue Jackets). While both were taken before the Maple Leafs’ 158^th pick (drafted Grant Rollheiser), they could’ve swooped in and taken them earlier in the fifth round.

The second-round pick in 2008 is a tough pill to swallow where the Maple Leafs could’ve had a potential Norris Trophy candidate. The Coyotes ended up moving this pick to the Nashville Predators for picks that became Colby Robak and Mathieu Brodeur. The Predators ended up selecting Josi.

Since he’s entered the league, he has been nothing but a consistent defenseman for the Predators, ultimately becoming their top defender and a Norris Trophy candidate. In his nine seasons, Josi has reached the 50-point mark five times and the 60-point mark twice. He has really emerged as one of the game’s top defenders, something the Maple Leafs have longed for quite some time. At a time when defense was becoming one of their weak points in their game, Josi could’ve been the backbone on the blue line and answer to their problems.

The Toskala Trade

To Maple Leafs: Mark Bell, Vesa Toskala
To San Jose Sharks: 2007 second-round pick (Pick traded to the St. Louis Blues, selected Aaron Palushaj 44th overall), 2009 fourth-round pick (Pick was traded to the Predators, selected Craig Smith 98th overall), 2007 conditional first-round pick (Picked traded to the Blues, selected Lars Eller 13^th overall)

This is another ugly one. The Maple Leafs were originally supposed to select 13^th overall in the 2007 Draft. The Sharks were able to move up in the draft, swapping picks with the St. Louis Blues. With that swap, the Sharks selected Logan Couture. 

If the Maple Leafs made the move with St. Louis instead of with San Jose, then the Maple Leafs could’ve had a potential top-line centre with over 700 games played and over 500 points. Goaltending was something that has haunted the Maple Leafs for years as Toskala didn’t pan out as many expected. After the Maple Leafs gave up Tukkaa Rask for Andrew Raycroft, they’ve gone through a revolving door of goaltenders and struggled for years to find a starter. 

Even if the Maple Leafs kept their 13^th overall pick, they could’ve added another strong puck-moving defenseman. They could’ve selected Kevin Shattenkirk who was always guaranteed at least 45 to 50 points as a defenseman.

Luke Schenn Over Erik Karlsson

To Maple Leafs: 2008 first-round pick (Luke Schenn, fifth overall) 
To New York Islanders: 2008 first-round pick (Pick was later traded to Nashville Predators, selected Colin Wilson seventh overall), 2008 third-round pick (Pick was later traded to the Chicago Blackhawks, selected Shawn Lalonde 68th overall), 2009 second-round pick (Pick became Anaheim’s, selected Mat Clark 37^th overall)

This completes the hat-trick of ugly draft pick moves for the Maple Leafs. They were originally supposed to pick seventh overall but moved up to select Luke Schenn fifth overall. They could’ve struck gold if they kept the pick and didn’t trade the seventh pick. 

Erik Karlsson and John Carlson have established themselves as all-star defensemen and since they were available, they could’ve been game-changing picks for Toronto if they were selected. Even Jordan Eberle was still on the board. Instead, the Maple Leafs picked a defenseman that was rushed into the league and never developed into anything with promise. The ceiling was high for both Karlsson and Carlson as they are both all-star defensemen in this league.

The Draft Bust

To Toronto: 2011 first-round pick (Tyler Biggs, 22nd overall) 
To Anaheim Ducks: 2011 first-round pick (Rickard Rakell, 30th overall), 2011 second-round pick (John Gibson, 39^th overall)

The Maple Leafs had two first-round picks in this draft. It wasn’t a mistake adding another first rounder, but more so the selections. The Maple Leafs could’ve had Rakell as well as John Gibson who selected with the second-round pick. They moved up to select… Tyler Biggs who never saw any game time what so ever. Along with Biggs, they selected Stuart Percy when both Phillip Danault and Vladislav Namestnikov were still available. Both picks could’ve been something as they’re both in the NHL. If they were drafting properly, the Maple Leafs could’ve had Rakaell and one of Danault or Namestnikov with their two picks.

Rakell has dipped in terms of production, but he’s still guaranteed 25 to 30 goals a season. And even if the Maple Leafs didn’t select Gibson in the second round, they had other options. They could’ve had a Stanley Cup champ in Brandon Saad or someone else by the name of Nikita Kucherov, who is only one of the top wingers in the game at the moment. 

Since 2016-17, Kucherov has been lights out recording over 80 points four times while hitting 100 points twice, averaging just over a point per game in his career. In addition, he’s been in the top 10 in goals and assists three times, while being in the top 10 in points four times in his career. The Tampa Bay Lightning eventually swooped in and 2018-19 Art Ross winner (128 points). This would’ve been a game-changing selection for the Maple Leafs. 

If the Maple Leaf kept their picks and selected properly, they could’ve had a long list of players including: Rakaell, Kucherov, Couture, Paul Stastny, Callahan, Letang, Josi, Yandle, Hjalmarsson and Gibson as well as one of Karlsson, Carlson or Eberle. That is a major abundance of NHL talent where they could’ve avoided multiple seasons of disappointment from 2005-06 to 2014. The team still could’ve been competing for the playoffs, instead of trying to cut corners and ultimately going into a full-blown rebuild. 

While we may not have the players that we currently have, things could’ve been a lot different if they kept their picks instead of trading them all away. The Maple Leafs’ loss was other teams gain and they’re greatly benefiting from that.

Information from NHL Trade Tracker.

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