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Looking Back: How The Last 15 Maple Leafs Draft Picks SHOULD Have Looked

The Toronto Maple Leafs have had an interesting existence since the turn of the century. In the early 2000s, they were a premium NHL ticket, boasting a passionate fan base and a veteran laden team tha

The Toronto Maple Leafs have had an interesting existence since the turn of the century. In the early 2000s, they were a premium NHL ticket, boasting a passionate fan base and a veteran laden team that featured the likes of Mats Sundin, Alex Mogilny, and Ed Belfour. Unfortunately, as the NHL transitioned into the salary cap era we now have learned to love, the Leafs' philosophy and drafting skills took a little while to catch up. Their futility since the lockout has been magnified by increased media scrutiny and the ongoing presence of social media, and it's only been since Brendan Shanahan took over as President in 2014 that the team has made any real progress.

The purpose of this is not to criticize a lack of foresight and point your finger at the Maple Leafs' scouting networks, but rather to look at the "what if's" and see how one well timed draft pick can alter a franchise for years, even decades.

We're going to take a look at every draft the Leafs used a first round pick in, and dream up the possibilities that could have been if they all just ate more fortune cookies and made the perfect pick every single time.

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15 1999: Henrik Zetterberg

Billy Hurst-USA TODAY Sports

Original Pick: Luca Cereda

There's no need to feel bad about this one Leafs brass, as there were precisely 209 players who were deemed better prospects than the current Detroit Red Wings Captain. Henrik Zetterberg joined the league in 2002, which would have had him playing in a top-six forward group featuring fellow Swede Mats Sundin, Alex Mogilny, Owen Nolan, and Darcy Tucker. That group made the playoffs in both 2003 and 2004, and with the possibility of adding a player of Zetterberg's caliber by simply standing at a microphone and saying "we select Henrik Zetterberg," the Leafs may have been able to avenge their Conference Finals losses in 1999 and 2002.

Unfortunately, with the 24th overall selected the Maple Leafs ended up selecting a Swiss center named Luca Cereda, who went on to play as many NHL games as me (zero).

14 2000: Henrik Lundqvist

Adam Hunger-USA TODAY Sports

Original Pick: Brad Boyes

With a second consecutive 24th overall pick, the Leafs did well with this one, selecting Canadian winger Brad Boyes. He would end up being traded alongside Alyn McCauley in order to obtain the services of power forward Owen Nolan.

While that was a solid pick, a better one would have been current New York Rangers goaltender, Henrik Lundqvist. Similar to Zetterberg, he was passed on 204 times before being scooped up with the 205th overall pick. Timing-wise, Lundqvist joined the league in 2005 which is exactly when the Leafs management realized that Ed Belfour wasn't going to cut it in the post-lockout era, and went and made that bone-headed move to trade Tuukka Rask for Andrew Raycroft. Had they been the ones to nab Lundqvist with any of the six picks they had before he was selected, they would have avoided a devastating trade, and perhaps would have had Henrik Lundqvist and Tuukka Rask in the system at once - two of the best goaltenders in the game today.

Oh well.

13 2001: Patrick Sharp

Jerome Miron-USA TODAY Sports

Original Pick: Carlo Colaicovo

Patrick Sharp was a snag for the Philadelphia Flyers at 95th overall, but unfortunately they gave up on him too soon to reap the rewards. He happened to win three Stanley Cups with Chicago shortly after, which is decent.

Sharp blossomed into a bonafide top line winger in 2007 with a 36 goal breakout campaign. From the Leafs perspective, it would have coincided with their third straight playoff-less season, and perhaps would have hindered their desire to throw speedy winger Jason Blake (remember him?) a $20 million contract. Would Sharp have been enough to elevate them to the playoffs? Tough to say, but their second highest scoring forward after Sundin that year was Nik Antropov, so surely some two-way scoring depth would have served them well.

Instead, they selected Carlo Colaiacovo at 17th overall, which wasn't a terrible pick, but certainly didn't alter the franchise in any significant way.

12 2002: Duncan Keith

Jasen Vinlove-USA TODAY Sports

Original Pick: Alex Steen

Duncan Keith might be the closest thing to Scott Niedermayer I'll ever see again, except that Niedermayer didn't surprise anyone since he was a third overall pick. Keith, however, had 15 defencemen selected before him prior to the Blackhawks choosing him with the 54th overall pick.

Keith began his NHL career in 2005 after the lockout-lost season. Should he have been a Maple Leaf, he would have suited up alongside Tomas Kaberle, Brian McCabe (who had 26 goals that season), and with Ken Klee and Alexander Khavanov as the immediate options behind him. well, surely the team would have been able to scrape out a couple more wins.

Instead, the Leafs snagged Alex Steen at 24th overall who has become a top line or top-six forward for the St. Louis Blues, but pales in comparison to Duncan Keith's three Stanley Cups, Conn Smythe as playoff MVP, and 2 James Norris Trophies.

11 2005: Tuukka Rask

Winslow Townson-USA TODAY Sports

Original Pick: Tuukka Rask

Yeah, the Leafs nailed this pick by snagging a franchise goaltender with a late first round pick at 21st overall. Unfortunately they ended up panicking after their narrow playoff miss in 2006 and traded the young Finnish stud for Andrew Raycroft, who only played 91 games for the Leafs.

Other options would be Pittsburgh Penguins defender Kris Letang or Los Angeles Kings goaltender Jonathan Quick, but realistically the Leafs would make this pick over and over again and hopefully not trade him next time. Supposing the Leafs would have kept Rask in Toronto, perhaps the young goalie could have flourished into a franchise netminder and saved the Leafs years of goaltending woes.

10 2006: Claude Giroux

Marc DesRosiers-USA TODAY Sports

Original Pick: Jiri Tlutsy

Everyone other than the Philadelphia Flyers expected Claude Giroux to become a sound offensive player with some creativity. The Flyers, however, were hoping for a bit more, and they certainly got it. Selected 22nd overall, Giroux exceeded all expectations by become an elite playmaking center with great vision and shiftiness.

Giroux' first full season was 2009-2010, which was also Toronto's first season with Phil Kessel in the mix. Other than "Phil the Thrill," the team's top performer's were Alex Ponikarovsky and Matt Stajan. So it looks like Kessel could have used someone who could distribute the puck on the level level that Giroux can.

Instead, they chose Jiri Tlusty who has been a decent depth forward for most of his career. With the arrival of Kessel though just as Giroux broke into the league, you can't help but think what a combination that would have been. Speedy playmaker, speedy sniper - 50 goals for Kessel?

9 2008: Erik Karlsson

Marc DesRosiers-USA TODAY Sports

Original Pick: Luke Schenn

In plain terms, Erik Karlsson is the best offensive defenseman in the game today. He slipped down to 15th overall in this draft, being chosen behind six other defenders.

Karlsson broke into the league one year later for the 2009-2010 season, the same season the Leafs acquired Phil Kessel and Dion Phaneuf. With Tomas Kaberle, Ian White, and Francois Beauchemin as the top-four defensemen on the team, an addition like Erik Karlsson would have elevated that group into the upper echelon of the NHL.

At fifth overall, the Leafs instead selected Luke Schenn who has been an okay defender for the last eight years. In defense of Schenn, the Leafs likely rushed him when he played his first season as an 18 year old, and he could have had more to offer if there was a bit more patience with the former WHL star.

8 2009: Ryan O'Reilly

Marc DesRosiers-USA TODAY Sports

Original Pick: Nazem Kadri

Ryan O'Reilly was the pick of the 2009 draft, slipping to 33rd overall when realistically he should have been a top-five slection out of this group.

Astoundingly, O'Reilly made the NHL as an 18 year old second round pick, a feat we rarely see occur in today's NHL. Should he have been able to crack the Leafs for the beginning of the 2009-2010 season, he would have added some nice depth, but it would be a few years later in 2013 when he really made his mark with a 28 goal, 64 point campaign. Toronto had a sound attack that year, with six forwards scoring 40 points or more, so a player like O'Reilly could have truly pushed them over the hump.

They selected Nazem Kadri at seventh overall instead who has developed into a strong two-way center for the team, but O'Reilly is a tier above in my eyes. Regardless, they certainly didn't make a bad pick as Kadri likely is a top 10 pick from that draft as well, but they could have added a bit more offense with a guy like O'Reillly.

7 2011: Nikita Kucherov

Kim Klement-USA TODAY Sports

Original Pick: Tyler Biggs

The Maple Leafs actually had two first round picks in the 2011 draft, selecting Tyler Biggs at 22nd overall and Stuart Percy with the 25th selection.

This draft could have been completely franchise altering for not just the Leafs, but for all 28 teams that let Nikita Kucherov slide to the end of the second round.

Kucherov played 52 games in the 2012-2013 season and put up an underwhelming 18 points. The following season, however, he exploded for 64 points and was even more impressive in the playoffs, tallying 22 points in 26 games.

With the Leafs having two first round picks in this draft, simply scroll down to see what a devastatingly dynamic duo the Leafs could have snagged just three picks apart.

6 2011: Johnny Gaudreau

Sergei Belski-USA TODAY Sports

Original Pick: Stuart Percy

Yep, it was possibly for every single team in the NHL to cash in on the brilliant skill sets hiding within Johnny Gaudreau and Nikita Kucherov.

Gaudreau joined the league in 2013-14 and put up identical numbers as Kucherov with 64 points in his rookie campaign. Should then-GM Bryan Burke have had a crystal ball, he could have made two selections that would impact the Maple Leafs for years to come with two of the best young wingers in the game.

If one could have added those two to complement a dynamic Phil Kessel, James van Riemsdyk, Nazem Kadri, Tyler Bozak, and Joffrey Lupul, you can see the Leafs would have a strike force that would be nearly unparalleled in today's NHL.

At least Stuart Percy has gone on to have a nice AHL career.

5 2012: Morgan Rielly

Brace Hemmelgarn-USA TODAY Sports

Original Pick: Morgan Rielly

The 2012 draft was the draft of the defenseman, where eight of the top 10 selections were blueliners. It is with this pick here that the Leafs slowly began to change the way the franchise operated.

Toronto selected fifth in this draft, choosing Morgan Rielly whom I believe they would choose once again if given the opportunity. Winnipeg's Jacob Trouba, Nashville's Filip Forsberg, Shayne Gostisbehere in Philadelphia, and Colton Parayko in St. Louis are my candidates as a replacement if I had to, but Rielly is further along the developmental road than that group.

With this pick, the Leafs added a top pairing defenceman to the mix, which is a crucial piece to any rebuild.

4 2013: Andre Burakovsky

Brace Hemmelgarn-USA TODAY Sports

Original Pick: Fredrik Gauthier

Andre Burakovsky was selected two picks (23rd) after the Leafs had selected Fredrik Gauthier with the 21st overall pick.

Gauthier is still proving he belongs in the NHL and he may become a valued contributor down the road, but Burakovsky has a much higher ceiling. The young Swede has played two seasons in the NHL, increasing his totals from 22 in 2014-15, and nearly hitting the 40 point benchmark with 37 last season. If his talented skillset were to be added to the likes of Auston Matthews, Mitch Marner, William Nylander, and the rest of the young Leafs, it's simple to see the dangerous attack that would be brewing in Toronto.

Instead, with Gauthier they get a low ceiling low risk player, and given the skill up front for the blue and white, maybe he'll end up being a valuable bottom-six player for the franchise down the road.

3 2014: Nikolaj Ehlers

Sergei Belski-USA TODAY Sports

Original Pick: William Nylander

Let me be clear: William Nylander (whom the Leafs actually chose), was a fantastic pick at eigth overall. But at just 20 years old, Nik Ehlers is hovering around the point per game mark and at the time of writing has 10 goals in his last 13 games.

In simple terms, he's a star.

Really though, you can go either way as Nylander and Ehlers make up the eighth and ninth picks of the 2014 draft. So long as you don't do what Vancouver and Carolina did with the sixth and seventh picks (select Jake Virtanen and Haydn Fleury) then you get a big shiny A+. With how dynamic and shifty Ehlers is (similar to Mitch Marner), a top line of Marner-Matthews-Ehlers looks ridiculously appealing, yet, much to the delight of Leafs fans, so does Marner-Matthews-Nylander.

Basically, it's a good time to be a Leafs fan.

2 2015: Mitch Marner

Tom Szczerbowski-USA TODAY Sports

Original Pick: Mitch Marner

Once again, the Leafs would keep this fourth overall selection as Marner has a sky-high ceiling and a combination of vision and hands that is rarely seen in the NHL. They'll tip their hats to the Arizona Coyotes for taking Dylan Strome at third overall, and enjoy the thousands of tickets that Marner will sell for them over the coming decade. He is dynamic.

A possibility to consider would be Zach Werenski (seventh overall) who went to Columbus and looks already to be a top defenseman in the game, but short of passing on Connor McDavid if he somehow fell to fourth for them, there will not be a sliver of regret when it comes to this pick.

It's a good time to be a Leafs fan.

1 2016: Auston Matthews

Robert Mayer-USA TODAY Sports

Original Pick: Auston Matthews

I sat here for about 10 minutes to decide whether I was going to be that guy who puts Patrik Laine here and it took some serious consideration.

The tiebreaker is that Auston Matthews projects what very few players ever project to be, which is a Mr. Everything center equipped with leadership. The challenging part is that Patrik Laine also projects to be the best goalscorer in the league at some point, but for where the Leafs are in the rebuild, the perfect center ice man would be impossible to pass up.

Comparisons include John Tavares, Steve Stamkos, and Jonathan Toews as the type of impact he will have for the city of Toronto. Centers of this ceiling rarely come along and when they're available, you take them and never look back.

One more time: it's a great time to be a Leafs fan.

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Looking Back: How The Last 15 Maple Leafs Draft Picks SHOULD Have Looked