The Leafs is a recent one. Twice actually.
First-the original Muskoka Five. This was the transition to the salary cap world that the Leafs had a very hard time adjusting to. Can't just go out and throw money at the best players anymore. Cliff Fletcher was brought in to "dismantle" the team and sell off the scraps to the highest bidder. It needed to be done.
At the February 26, 2008 trade deadline, the team was 27-28-9 and some felt trades could net some good, young players to begin a rebuild. It was not to be. The Leafs made only 3 deals… Hal Gill, Wade Belak and Chad Kilger traded for a net 3 draft picks in 2008 (rounds 2, 3, 5) and a 5th round 2009 pick. The team went 9-7-2 to close the season, missing the playoffs again. The focus fell onto 5 players who had no-trade clauses (given by former GM John Ferguson Jr.), and had refused to waive them. These players were thought the Leafs’ most valuable commodities; trading one or all could potentially restock Toronto for the future. Mats Sundin, Tomas Kaberle, Darcy Tucker, Bryan McCabe and Pavel Kubina. They’d come to be known as The Muskoka Five.
The rumour of what happened was as follows: Fletcher had some deals lined up. Sundin felt that "they could still make the playoffs" and talked the rest of the guys into not waiving the no trade clauses, so the only futures aquired were for second string players. It was a bitter topic for Leafs fans, dividing fans along the pro vs anti Sundin lines.
So then Burke comes in, and arrogantly proclaims that he can rebuild the team in five years. Starts by making the horrendous Phil Kessel deal. Then the Phaneuf deal. Then Lupul. So now we have a team full of castaways from other teams, draft smaft!
It wasn't until the current regime came in and did what the fans said needed to be done since 2006. Trade off what you can for futures, bottom out, get a top pick, and reboot.