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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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