Nonis: Clarkson signing, Bolland trade, Phaneuf signing, etc.
Burke: Kessel trade, Komisarek signing, etc.
Fletcher: Steen trade, Finger signing, etc.
JFJ: Rask trade, failure to prepare for the new NHL, etc.
These guys wrecked the team before getting their feet wet and spent the rest of their time cleaning up their own messes.
Nonis' bad move was signing Clarkson but Bolland was a good move as he was good for the team while healthy, barring a freak injury the Leafs and Bolland might've had a better relationship when it came to re-signing him, and they could've worked a deal out for better AAV than what he took in FLA.
IMO, the bigger issue was the Grabovski buyout, letting MacArthur walk, and letting Kulemin walk.
However, Nonis was instrumental in bringing in Phaneuf in the first place, and whatever you may feel about him, he is an asset that the Leafs can convert, if they choose, in a trade that will bring back valuable assets.
Burke's Kessel deal still looks good. Add to that all the other trades in his tenure, and the Leafs would be way, way, way, further back organizationally without Burke coming in.
I voted for Fletcher, although it was close with JFJ. The Rask trade was pretty bad, but there was no way to predict that Rask would be THAT GOOD, or that Pogge would be THAT BAD, or that Raycroft would be THAT BAD.
Fletcher unloaded Colaiacovo, Steen, signed Finger to an absurd deal, totally effed up the Tucker and Sundin situations, traded Bryan McCabe for a 4th and Mike Van Ryn who basically never played a game for the Leafs...
Fletcher was tasked with dismantling the team for a rebuild and he did it exactly the way that HFBoards thinks it should be done. Sell everyone off at rock bottom prices so that you suck and end up drafting high picks for the next few seasons.
In fact it's much more intelligent to sell off players at the best price possible to maximize asset value, in order to start the rebuild with a solid base of assets.
As a comparable, let's imagine that Shanahan becomes the next GM of the Leafs, and trades Kadri, Phaneuf, Gardiner, Komarov, and Bozak for a 4th round pick. Not each. All together for a 4th round pick.
You'd all lose your effing minds.
That's basically what Fletcher did.