There is always interesting about looking back on earlier NHL draft years. Seeing where players started their careers to see where they ended up later on. And there is an enjoyment in looking back with hindsight.

When thinking about NHL draft busts there are always two names that first come to mind. Alexandre Daigle, who was drafted in the 1993 NHL draft by the Ottawa Senators and Patrik Stefan who was drafted in 1999 by the Atlanta Thrashers. They were expected to be the next stars of the NHL but ended up being disappointments.

In relation to choices like that, the Toronto Maple Leafs have been lucky. Every time the team has been bad enough to draft a legitimate star they’ve made the right choice, specifically during the ’80s and the last few years. But they’ve made their own fair share of mistakes when drafting players that have held the Leafs back from becoming a better team until now.

#5 Carlo Colaiacovo

It’s unfortunate that Carlo Colaiacovo is on this list. He had the makings of being a good defenseman, but his career was hampered by constantly getting injured.

(Amy Irvin / The Hockey Writers)

The Leafs drafted Colaiacovo 17th overall in the 2001 NHL entry draft. He had a good draft year with 39 points in 62 OHL games with the Erie Otters. He then spent six years in the Leafs organization, splitting time between the Leafs and the Toronto Marlies, battling injuries throughout that time. His best season with the Leafs was in the 2006-07 season when he played 48 games and had 17 points.

The Leafs ended up trading Colaiacovo as part of the Lee Stempniak trade. Colaiacovo then spent four seasons with the St. Louis Blues where he seemed to finally live up to his potential. He played at least 60 games in each of the four seasons with the Blues and had more than 20 points in three of those seasons. After the 2011-12 season he bounced around a few teams while struggling to stay healthy.

Despite the injuries, Colaiacovo is currently playing in the DEL hockey league for the Mannheim Eagles. He has 14 points in 18 games but again has missed most of the season because of injuries. It is interesting to think of what his career could have been if he was able to stay healthy.

#4 Luca Cereda/Leafs 1999 Draft Picks

The 1999 NHL entry draft was a terrible year. There were a few stars that came out of it like Henrik and Daniel Sedin and Henrik Zetterberg, but this year is mainly remembered as the year that Stefan was drafted first overall by the Thrashers.

People focus on Stefan when looking back on the 1999 draft, which is lucky for the Leafs because it is literally the worst draft year in team history. Now you may think I’m exaggerating, but again — it is the worst draft year in Leafs’ history.

The Leafs drafted nine players that year with only one player seeing a single NHL game. That was Pierre Hedin, who was drafted in the eighth round, and he only played three games. That is the least amount of NHL games played from a draft year in Leafs draft history.

Luca Cereda was the Leafs first round pick that year, coming in at 24th overall. It’s strange that he was picked in the first round when there is nothing that’s particularly impressive about his stats, aside from having 10 points in seven games at the 1998-99 Under-18 World Juniors. His best year with the Marlies, then the St. John’s Maple Leafs, was 25 points in 68 games in 2002-03. He went back to play in Switzerland after spending three years in St. John’s.

The Leafs entire 1999 draft year can be summarized in one fact. Of the 28 players selected in the first round of the 1999 NHL entry draft, only Cereda and two other players ever played a single game in the NHL.

#3 Justin Pogge

Looking back on Justin Pogge‘s career gets sadder and sadder with every detail and fact that’s brought up. For a goalie that was drafted 90th overall in the third round of the 2004 NHL draft, expectations were unrealistically high.

Justin Pogge (Photo courtesy Gregg Forwerck, Carolina Hurricanes)

After being drafted by the Leafs he spent another two years in the WHL and was fantastic. He had a .917 save percentage in the 2004-05 season after being traded to the Calgary Hitmen and then improved on those numbers the next season with a .926 save percentage.

If that wasn’t promising enough for the Leafs, Pogge was part of Team Canada for the 2005-06 World Junior Championship. Pogge helped lead Canada to the gold medal with an astounding 1.00 goals against average and a .952 save percentage in six games.

Tuukka Rask (Bob DeChiara-USA TODAY Sports)

Pogge was then projected to be the Leafs’ “goalie of the future”. With that set, it meant the Leafs other goalie prospect became expendable — some goalie named Tuukka Rask.

In the summer of 2006, the Leafs traded the rights of Rask to the Boston Bruins for Andrew Raycroft. That is now remembered as one of the worst trades in team history as Raycroft wasn’t able to regain his form that won him the Calder Trophy in 2004. Rask, on the other hand, went on to become the Bruins starting goalie, still is, and is one of the best goalies in the NHL.

Pogge spent three seasons as the starting goalie for a terrible Marlies team and posted unimpressive numbers. In the 2008-09 season, he finally got a chance with the Leafs. He played seven games, allowing 27 goals and having dreadful numbers with a 4.36 goals against average and a .844 save percentage. That Leafs’ team was just as bad as the Marlies with Jason Blake being the Leafs best player, remember those years?

That summer the Leafs knew that their “goalie of the future” wasn’t going to pan out. They shipped him off to the Anaheim Ducks for a 2011 sixth round pick. He then played in the AHL for a few years before heading off to Europe. Pogge is currently playing in the KHL.

Pogge was a goalie that showed tremendous promise and was, unfortunately, held to unreasonable expectations while being hampered by the poor teams in front of him.

#2 Tyler Biggs

Oh boy, Tyler Biggs. Everything about drafting Biggs is mind-boggling.

During the 2010-11 season, the Leafs traded Tomas Kaberle to the Bruins for Joe Colbourne and their 2011 first round pick — the Bruins would go on to win the Stanley Cup so that draft pick would be 30th overall.

So, the 2011 NHL draft comes around and the Leafs have their eye on a big truculent player in Biggs. So the Leafs decided they would move up in the draft by trading the first round pick, 30th overall that they got from the Bruins, and a second round pick, 39th overall, to the Anaheim Ducks.

Tyler Biggs (Ross Bonander/THW)

In return, the Leafs moved up to 22nd overall and drafted Biggs. It’s important to point out that the Leafs had another first round pick at 25th overall, which they used to select Stuart Percy.  So, what happened to the draft picks that the Leafs traded to the Ducks you might ask? Well, the 30th overall pick became Richard Rakell and the 39th overall pick became John Gibson, the Ducks current starting goalie.

The only thing more painful than looking at that trade in hindsight is looking at Biggs’ stats after being drafted. Now, before getting into the bad numbers, Biggs did have two okay seasons. In his draft year, with the U.S. National Development Team, he had 11 points in 20 games. That’s okay, but nothing worth a first round draft pick. The second was in 2012-13 when he played for the Oshawa Generals in the OHL and had 53 points in 60 games.

He then spent three seasons with the Marlies, his best season being the 2013-14 season when he had nine points in 57 games. That’s as good as it got for Biggs. He was then thrown into the Phil Kessel trade with the Pittsburgh Penguins so that the total value of the contracts going back and forth were even. Biggs is now playing in the ECHL for the Kalamazoo Wings and has 19 points in 39 games.

Biggs was a bad choice even before he was drafted. It also didn’t help that the Leafs gave up two future NHLers for him in Rakell and Gibson.

#1 Luke Schenn

And lastly at number one, Luke Schenn.

(Amy Irvin / The Hockey Writers)

The sad thing is that he might have had a great career if he was drafted a decade earlier. By 2008 the NHL had started to shift to a faster game, which in turn made big slow defensemen a liability. Schenn always put up big hits and even managed to contribute a bit offensively. But the new age of the NHL had come and Schenn was one of the casualties.

The Leafs, like we’ve seen before, traded up in the 2008 NHL draft to pick Schenn at fifth overall. To get that pick the Leafs traded the seventh overall pick, a third round pick and a second round pick in 2009 to the New York Islanders. Unlike before, the only pick the Leafs traded that panned out was the seventh overall pick — the Islanders ended up trading down in the draft and the Nashville Predators drafted Colin Wilson seventh overall.

Schenn was expected to be the new face of the franchise for the Leafs. The problem was that the Leafs couldn’t wait. They put him in the lineup immediately instead of letting Schenn develop more in the WHL.

He did manage to look okay in his rookie year during the 2008-09 season, which was also the year Pogge played his seven games for the Leafs. Schenn’s career point totals came in the 2010-11 season when he finished with five goals and 22 points and he matched that total the next season as well.

There was talk that he would be the Leafs future captain, but that was no longer the case after four seasons in Toronto. By then the cracks had become obvious. During the summer of 2012, the Leafs traded Schenn to the Philadelphia Flyers for James van Riemsdyk, who has since been one of the Leafs’ best players. Schenn then spent four seasons with the Flyers and a season with the Los Angeles Kings. Schenn is now playing for the Arizona Coyotes.

Who would be on your list of the Leafs top 5 draft busts?