It is no secret that Toronto Maple Leafs management have really messed up over the last 10 or so years. The easiest way to confirm that is to look at the current state of the team, which is considered one of the worst in recent seasons. The neglect of thinking about the long term has caused Toronto to trade away their future for something that will help them in the short term, and guess what? That "long term" neglect is being felt right now.
To start, here are the numerous poor management decisions, lop-sided trades, and bad drafting done by Toronto. Some are well known, and others not so much. We'll begin with the known and end with the new:
*All pictures obtained from nhltradetracker.com*
Toronto had Rask... Yes the Leafs actually drafted him and decided to trade him when he was a prospect for an established NHL starter. Raycroft wasn't around for long, and Tuukka developed into one of the best goalies in the league. This one stings big time.
There is no denying that Kessel is elite, but the reality is so is Seguin. And on top of that Toronto could have had future star defenceman Dougie Hamilton as well. Seguin would have been the Leafs #1 centre they so desperately been lacking and Hamilton the #2 defenceman the team needs. The price was steep for Kessel, and although he has played amazing for the team over the years, the package Toronto gave up was far too much.
The Blackhawks knew Bolland's trade value was sky high because of his Stanley Cup winning goal, and took advantage of the Leafs because of it. Toronto's prospect cupboard doesn't match those of the rest of the league because of all the picks they have traded away; and three were sent to Chicago in this trade. A second round pick still has high value, and the Leafs seem to have given away players for the future for one that played only one season in a Leafs uniform and then took off in free agency. We don't know the full extent of this trade until we see what becomes of the players Chicago drafted, but if its anything like their track record, it won't be in favour of the Leafs. The point is, those three picks could have helped Toronto re-stock their prospect pool.
The Leafs received Boston's 30th overall pick in the Tomas Kaberle trade, and then flipped it to Anaheim along with their second rounder to move up in the 2011 draft. The player they moved up to take (Tyler Biggs) has so far been dubbed a bust as he's barely managed playing time in the AHL, while Anaheim picked up Rickard Rakell (who plays on their 3rd or 4th line) and John Gibson (one of the best goaltending prospects). The Leafs traded up for an AHL player and in the process gave up a solid 3rd or 4th line player and a future NHL starting goaltender in the process. Gibson has shown his dominance in the AHL and even in his brief stint with the Ducks this season, and it definitely hurts to know he was taken with the Leafs old pick.
Another time Chicago seemed to take advantage of the Leafs was when Toronto gave up the pick that landed the Blackhawks Brandon Saad; a useful winger on the 1st or 2nd line. He's up for a big raise this offseason as Saad is a RFA, and is sure to command a hefty salary that reflects his current stellar play. He is a very useful 2-way forward who has the ability to score, but also plays a solid defensive game as well (which is evident when he plays on Chicago's penalty kill).
Joe Colborne was also aquired from Boston in the Kaberle trade, and the Leafs never even gave him a shot. In the 2012 season, he was barely played and seemed to not have a role on the Maple Leafs despite his checking-line ability. On Calgary he plays as a penalty killer on on their 3rd line (checking line) and is showing his effectiveness on the ice. His big size lets him move around wherever he wants, and Toronto just traded him away to get under the 23-man roster limit before the 2013-2014 season began. In the 2012-2013 season, Colborne played 5 games for the Leafs and 65 in the AHL. The next season in Calgary, he played 80 games in the NHL. That's why this trade is lop sided, because Toronto didn't recognize his usefulness and decided he was the contract they were going to trade away to get under the roster limit. The 4th round pick the Leafs got was traded to St. Louis along with Carl Gunnarsson for Roman Polak last offseason.
The trade itself wasn't bad. The bad part revolves around the 3rd round draft pick the Leafs sent to Anaheim. The pick was a conditional pick, meaning if Holland played a set amount of games for Toronto in the 2013-2014 season, the draft pick would change from the Leafs 3rd round pick to their 2nd round pick. The Leafs had 3 of their centres injured, so they acquired Holland to bring a NHL ready body into the lineup. When everyone became healthy, ex head coach Randy Carlyle decided Holland was best used on the 4th line along with enforcers Colton Orr and Frazer McLaren. That means he was playing around 5 minutes a night, and in the end he played a large amount of games for the Leafs and the pick became a 2nd rounder in the 2014 draft. As I said before, 2nd round picks still hold value and Toronto gave theirs away because Holland played the conditional amount of games by playing only 5 minutes a night in the majority of them. If he was going to play that little, management should have sent him to the AHL so the pick would have stayed a 3rd rounder, but instead they let Carlyle play Holland on the 4th line with next to no playing time and it cost them a high draft pick. Acquiring Holland was smart because of all the injuries that they had at the time; however wasting the pick because they didn't send him to the AHL when they should have was costly. It proves to be an even bigger mistake because the Leafs also don't have a second round pick in the 2015 draft because of the Jonathon Bernier trade, meaning this is the 3rd consecutive season that they won't be picking in the second round. 2013 pick was gone for Bolland, 2014 for Holland, and 2015 for Bernier.
There are a couple of good trades the Leafs made (Ex. JVR for Luke Shenn, Kris Versteeg to the Flyers etc.) but the fact is that the picks and prospects the Leafs gave away the last decade hurt them in the long run, which is being felt now. Other teams saw the importance of the draft (especially in the salary cap era), and stalked up on picks while Toronto thought nothing of theirs and gave them away. With the many collapses happening to the team, and a lacking prospect cupboard, the philosophy in Canada's biggest city has finally changed under the rule of President Brendan Shanahan. He has begun a proper re-build through the draft, but Leafs fans all around agree that this should have happened way sooner.
Now it's time to have some fun. To put it in even more perspective, if the Leafs hadn't traded their picks away in some of these trades, here is what the roster could have looked like if they drafted the players taken with their picks:
*Holland trade still stands because they would have traded for him anyway with all the injuries at the time*
Van Riemsdyk, Seguin, Saad
Lupul, Kadri, Panik
Komorov, Bozak, Holland
Bailey, Colborne, Rakell
And on defence:
Rask, Reimer, or Gibson
This roster on paper looks much better than the one the Leafs currently had. The Leafs wouldn't have traded for Bernier with three NHL goaltenders already under contract, and would have a true number one centre in Seguin (who's production equals that of Kessel). Seguin on the roster means Bozak and Kadri get pushed down the depth chart a bit to better suited roles. The Leafs would have a much complete roster, and it would have on it some role players with some stars. Production would be high from their top two forward lines and defence as well (with the likes of Phaneuf, Hamilton, Gardiner and Reilly). For once they would have also had a very useful 4th line with Colborne, Rakell, and Bailey on it, and have great depth throughout their lineup. More of their roster players would have been their own draft picks, instead of their current one which is comprised from mostly trades and signings.
To end, here's some pictures of the players the Leafs could have had: