Up until this past season, it has been incredibly hard being a fan of the Toronto Maple Leafs. The stubborn franchise had been run by inept management for over a decade, failing to adapt to the salary cap era and making continual long-term signing mistakes (Dion Phaneuf, Joffrey Lupul, David Clarkson). Brian Burke, John Ferguson Jr. and Cliff Fletcher, among others, are names that fans of the team cringe every time they hear or read (sorry), and with good reason.
Not only has management handed out terrible deals in recent history, what infuriates fans most is the fact that they have dealt promising prospects and high draft picks for players that simply weren't going to get them over the top. Additionally, the team hasn't exactly had the best history at the draft - at least up until 2014 - and, while every team has its regrettable mistakes, the Maple Leafs might have the worst drafting record in the first decade-plus of the 21st century. If you feel like torturing yourself, browse the accompanied list below of 15 players that very easily could have been playing in Toronto. And if it's too much to take, just remember these three names: Auston Matthews, Mitch Marner, and William Nylander.
15 Tuukka Rask
We'll get the super obvious out of the way. Finnish netminder Tuukka Rask is arguably one of the NHL's best goaltenders, having compiled a 206-124-51 record, .923 save percentage, and 2.24 goals against average in 401 regular season games with the Boston Bruins. He won a Stanley Cup with the team, albeit as a backup, and won a Vezina Trophy in 2013-14 as the league's top goaltender.
Rask not only could have been a member of the Toronto Maple Leafs, he kind of was. In what might be one of the organization's best value picks in recent memory, Toronto drafted Rask with the 21st overall pick in 2005. At the 2006 World Junior Championships, Rask single-handedly led Finland to a bronze medal, while fellow Maple Leafs prospect Justin Pogge was the benefactor of a dominant Canadian team which won the gold medal with ease. Rather than develop competition between two quality prospects, the Leafs traded Rask to Boston for Andrew Raycroft in what might be the worst trade in franchise history.
14 Tyler Seguin
As if the Maple Leafs didn't do the Boston Bruins enough favors by sending them an All-Star goaltender for a bum who would be out of the league in a few years, Toronto handed the Bruins a pair of first round picks and a second round pick for budding sniper Phil Kessel in 2009. Brian Burke was the token inept General Manager at the time and, not realizing the Leafs were in need of a rebuild, he opted for a win-now approach by trading for Kessel.
Had the Maple Leafs been in a position to win a championship, it might have been a smart move. Instead, the team bottomed out the following season, meaning Boston picked second overall with the Maple Leafs first round selection. The Bruins picked Tyler Seguin, who is, at the very least, equal to Kessel in terms of offensive ability.
13 Dougie Hamilton
Keeping with the above trade, the Maple Leafs performed slightly better during the 2010-11 season, but again failed to make the playoffs, which meant the Bruins picked ninth overall with what was originally the Maple Leafs' pick. Boston selected defenseman Dougie Hamilton with the pick, but interestingly enough, both Hamilton and Seguin have since moved on from Boston and Kessel has moved on from the Maple Leafs.
Still, it's hard for the average fan to move on from just how bad this deal was. Not only was Kessel not what the Maple Leafs needed, a young core consisting of a talented playmaker and a budding defenseman, which is still an area of need, would have fast-tracked a rebuild that would have significantly altered Toronto's trajectory.
12 Dmitry Orlov
Toronto has a young core of players with a bright future, but the one problem is most of those players are forwards. Apart from Morgan Rielly, Jake Gardiner, and maybe Nikita Zaitsev, the Leafs have no real depth on defense. We saw that area of weakness exposed in the first round of the playoffs as players like Martin Marincin and Connor Carrick earned regular minutes. On the other side of the ice, however, was a blueliner Toronto could have easily had in the 2009 NHL Draft.
Dmitry Orlov was selected 55th overall by the Capitals and has since recorded 93 points in 283 games, while playing top-four minutes for most of his career. Five picks earlier, the Maple Leafs selected American forward Kenny Ryan with their first pick of the draft. Ryan played in the ECHL last year, while their other second round pick, Jesse Blacker, a defenseman taken three picks after Orlov, played in Germany.
11 Boone Jenner
This one might perhaps be the most frustrating situation on this list. When Brian Burke was General Manager of the Maple Leafs, he made it pretty clear he was determined to bring in hard-working American players, which was fine by most Maple Leafs fans as long as those players were actually talented. He also wanted physical, hard-hitting forwards, regardless of whether or not they could keep up with the pace of the NHL game.
That's why the Maple Leafs drafted Tyler Biggs with the 22nd pick in the 2011 NHL Draft. Biggs is just one of two players taken in the first round to have not played a game in the NHL; in fact, he hasn't even been able to secure a spot in the AHL. Meanwhile, there was a capable Canadian who played a similar style as Biggs but could actually skate; Boone Jenner, who was selected 15 picks later, but was exactly the type of player Burke was looking for. He had even recorded 66 points in his draft year, while Biggs had just 11 in 20 games for the U.S. National Development Team.
10 Milan Lucic
The fact the Maple Leafs passed on Milan Lucic in the 2006 NHL Draft is a little easier to take given they drafted Nikolai Kulemin six picks earlier, but it's hard not to imagine how big of a fan favorite "Looch" would be in Toronto. Kulemin, for his part, was once a 30-goal scorer with the Maple Leafs and was an adept penalty killer, but he was nowhere near as good as Lucic in his prime.
When the Maple Leafs signed David Clarkson to a regrettable deal a few years ago, they wrongly believed he could play a role similar to that of Lucic. Yet, they could have had Lucic himself if they took him with the 44th overall pick in 2006. Still, you have to give most of the credit to the Bruins scouting staff as Lucic had just 19 points and 149 penalty minutes in 62 games in his draft year. Few could have predicted he would explode for 68 points the following season and quickly become one of the NHL's most feared players.
9 Pekka Rinne
Pekka Rinne is one of the main reasons the Nashville Predators have advanced to the Western Conference Finals, which makes it even more absurd to think he was drafted in the eighth round, 258th overall by the Predators in the 2004 NHL Draft. Sure, you could argue that every team in the league could have had Rinne in the first eight rounds, but Toronto used its first pick in that draft, 90th overall, to select Justin Pogge, a goaltender out of the Western Hockey League.
Pogge was a great goaltender at the junior level, but a massive flop as a pro. He was also the reason the team traded Tuukka Rask despite investing in him with a first round pick. Had the Maple Leafs drafted Rinne in 2004, who knows what might have happened in regard to the goaltender situation? One thing is for certain, Leafs fans might never have had to be familiar with the names Andrew Raycroft and Vesa Toskala.
8 Brandon Carlo
Again we get back to the Maple Leafs need for defensemen. As fans, we're always told it takes longer for defensemen to develop and make an impact at the NHL level. Three to five years is the target; yet, that isn't always the case. Brandon Carlo is a prime example of the exception to the rule. The former Tri-City American blueliner was selected by the Bruins (who, if you haven't noticed, have been a perfect foil to the Maple Leafs throughout the years) with the 37th overall pick in the 2015 NHL Draft.
Perhaps the Leafs were hoping to stay away from the name Carlo given the failed Carlo Colaiacovo project a decade earlier, but Brandon Carlo has already become a solid defenseman. He played all 82 games for the Bruins during the 2016-17 season and recorded 16 points, while logging hard minutes against top opposition. Toronto selected defenseman Travis Dermott three picks before the Bruins selected Carlo, and while the Leafs are still high on Dermott, it's not hard to imagine the 6-foot-5 Carlo in a Leafs jersey.
7 Noah Hanifin
All of the aforementioned players would have made the Maple Leafs a much better team had the organization either not traded them or drafted them instead of the scrub they did pick. Noah Hanifin, while a solid young defenseman, would have been a disastrous pick for the Maple Leafs in the 2015 NHL Draft. In fact, this might be the one instance where Toronto defied common sense for the betterment of the club.
The Maple Leafs owned the fourth overall pick in 2015 and used it to select crafty playmaking forward Mitch Marner, who has quickly become a fan favorite. By all accounts, many executives in the organization wanted to select defenseman Noah Hanifin, especially since defense has long been a weakness for the team. It might have been tough to watch Hanifin, who was taken after Marner by the Hurricanes, played a prominent role for Carolina during the 2015-16 season, but Marner continued to develop in junior and is now an integral part of Toronto's success.
6 Steven Stamkos
Fans outside of Toronto get annoyed by the continual rumors and discussion of hometown players returning to sign in Toronto. Even with Auston Matthews in the fold, we're probably going to hear John Tavares rumors in the next year; last year, it was all about Steven Stamkos. The pending free agent was asked about his contract uncertainty in Tampa Bay throughout the 2015-16 season and, while he eventually re-signed with the Lightning, it was clear he wanted to entertain offers.
Toronto was certainly on the map for Stamkos, as he returned home in the 2016 offseason and, by all accounts, met with Maple Leafs executives and was even offered a large contract. Seemingly out of nowhere, following a meeting in Toronto, it was announced Stamkos was re-signing in Tampa Bay. It was a decision that stung a bit at the time for Maple Leafs fans, but in retrospect his cap hit would have strapped the team for years to come. As strange as it is to say, Toronto is better off without Stamkos.
5 Andre Burakovsky
Going back to the narrative of Toronto wanting big, strong, physical forwards, the team selected Frederik Gauthier of the QMJHL's Rimouski Oceanic with the 21st overall pick in the 2013 NHL Draft. "The Goat," as he is affectionately referred, has since played 28 NHL games, tallying two goals and two assists. At his absolute best, he's a fourth line center who might carve out a regular role in the future, which isn't exactly a ringing endorsement for a first round pick.
Two picks later, the Washington Capitals selected talented winger Andre Burakovsky out of Sweden. Remember, this was before Toronto had any prospects who were considered skilled, yet they opted to take a player known for his ability to win faceoffs over a player who, a year after being drafted, put up 87 points in 57 games in the Ontario Hockey League.
4 Erik Karlsson
As each season goes by, it becomes harder and harder to believe Erik Karlsson lasted until the 15th pick in the 2008 NHL Draft. You could easily make the argument he's the best player taken in the draft, ahead of both Steven Stamkos and Drew Doughty, who went first and second, and while 14 teams had the opportunity to add the future Hall of Famer, it's depressing as hell to think that the Maple Leafs selected Luke Schenn fifth overall when Karlsson was still on the board.
It's hard to truly fault Toronto, however, as Schenn looked poised to become the shutdown defender the team needed after an impressive 18-year-old rookie season. Back then the organization was still struggling to adjust to the new NHL, hell bent on drafting physical players with limited offensive capabilities, whereas current management has committed more to skilled players. If they had done so a decade earlier, things would be a lot different in Toronto.
3 Sebastian Aho
We mentioned earlier that the Maple Leafs passed up on a chance to draft 6-foot-5 defenseman Brandon Carlo with the 34th pick in the 2015 NHL Draft. And if that miscue by management wasn't enough, the Carolina Hurricanes selected Finnish forward Sebastian Aho 35th overall, one pick after Toronto selected Travis Dermott. Aho was already an effective player at the senior level in Finland, which is no small task for a 17-year-old, and he proved himself as one of the NHL's most exciting young players in 2016-17.
The speedy winger scored 24 goals and added 25 assists for the Hurricanes in his rookie season, and if not for an impressive draft class led by Auston Matthews, Patrick Laine, and Zach Werenski, Aho would be a strong candidate for the Calder Trophy. It's true the Leafs needed to take a defenseman, but there's no denying that Aho is by far more valuable than Dermott.
2 Jeff Carter
Whereas most of the players on this list could have been Maple Leafs through the draft, Jeff Carter was once actually rumored to be coming to Toronto during the prime of his career. Carter scored 29 goals and added 24 assists during the 2007-08 season and the Philadelphia Flyers viewed him as expendable, as long as they could add a defenseman. They set their sights on Maple Leafs' Tomas Kaberle, who, at the time, was one of the league's top offensive defensemen.
Unfortunately for the Maple Leafs and their fans, Kaberle had a no-trade clause, as did most of Toronto's players back then. Apparently the Flyers and Maple Leafs had actually agreed on a deal, which would have sent Carter AND a first round pick to Toronto in exchange for Kaberle.
1 Connor McDavid
It stings a little less now that the Maple Leafs perfected the tank in 2015-16 and won the draft lottery, giving them the right to select Superstar Auston Matthews. However, a year prior Toronto was in the mix for the top pick and a Toronto boy, Connor McDavid, was in studio during the lottery with hopes of the Maple Leafs winning the right to select him. And it almost happened.
Immediately after the Edmonton Oilers won another draft lottery, reporters began sharing the likelihood of Toronto winning the lottery to the frustration of Leafs fans everywhere. Sportsnet's Chris Johnston tweeted that, "After 5-14-6 were picked, the #leafs had the highest chance of getting McDavid heading to last ball: TOR (4x), BUF (3x), EDM (2x) CAR, CBJ." McDavid has revitalized the Oilers franchise, but can you imagine what he would have done in Toronto? Think Matthews but amplified.