Sorry for the double post
This is when the team started to get ugly. JFJ had no answers to the damage he was doing to the system and farm for the Leafs. He kept trying to block the holes in the ship but water was sinking his ship way too fast. Giving no trade clauses to players like Sundin, Tucker, McCabe, Kaberle and Kubina which handcuffed the team from gaining any assets to recover from. JFJ in his last ditch effort to keep his job traded Gill, Belak and Kilger for picks but he also traded his 1st, 2nd and 4th round picks to pick up Toskala and Bell. He also picked up Blake in FA by giving him a huge contract at the time. He was fired this year when the team was near the bottom of the standings late in the season but the damage was already done with bleak hope.
The next three seasons were probably the worst consecutive seasons I've seen as a fan. The 2007-2008, 2008-2009 and 2009-2010 seasons were quite the lesson for the Leafs management.
Your 2007-2008 Leafs
Steen-Sundin-Blake
Ponikarovsky-Antropov-Tucker
Wellwood-Stajan-Tlusty/Bell
Kilger-Moore-Devereaux
Pohl, Newbury, Belak
Kaberle-McCabe
Kubina-White
Gill-Colaiacovo
Wozniewski, Stralman, Kronwall
Toskala
Raycroft
Clemmensen
Finished 12th in the east and only when JFJ was fired did they realise how much damage he did to this entire organization. Peddie even said the hiring of JFJ was "a mistake" but it was too late. Cliff Fletcher was brought in to end the year but really he was put on the spot and I don't put any blame on him in the situation he was in. Schenn was drafted and retooling of the Leafs organization was underway.
2008-2009 Leafs
Ponikarovsky-Stajan-Blake
Hagman-Grabovski-Stempniak
Hollweg-Mitchell-Mayers
Devereaux, May, Williams, Hamilton, Tlusty, Deveaux
Kaberle-Kubina
White-Schenn
Finger-Frogren
Van Ryn, Sifers
Toskala
Joseph
Gerber
Pogge
Probably the worst lineup this team has iced in a very long time. I'm pretty sure Joseph was brought in just to distract the fans from their on ice play. Fletcher was told to clean house for the next GM and he did just that. Be it a bad trade or letting players go, this team was gutted and beaten to the point that it didn't look like the Leafs.
When Burke's contract was done with the Ducks he came over to try and salvage the wreckage. Burke noticed that the team had no potential elite talent and he brought in elite talents in Kessel and Phaneuf that year. Burke kind of had more of a retooling mentality rather than a full rebuild. He brought in Komisarek, Beauchemin and Gustavsson. Everyone knew the Leafs would finish low but nobody predicted that the Leafs would finish as low as they did. Although if Burke didn't make the Kessel trade, I doubt the Leafs would have snapped their playoff drought in 7 seasons. I bet it would have taken even longer.
Somewhere in the 2010-2011 season is where Burke changed his mentality for the club. He had traded for Versteeg before the season started and was putting together a better team than the season before. When Feburary came Burke started dealing players for picks and prospects, filling up the bare cupboards. Burke traded Versteeg, Kaberle and Beauchemin for two 1st's, a 2nd, 3rd, 4th round picks and Colborne, Gardiner and Lupul. This imo is when the Leafs youth movement really began.
The rest is so recent that it's not even worth going into.
So...TL;DR version.
The Leafs missed the playoffs for 7 straight years cause JFJ screwed us and because Burke had a change of heart when it came to evaluating the club.
Without this series of events though, I doubt we have a young up and coming team like we do now. Glad everything is working out so far and hope it continues to trend upwards.