To me, it was when the Leafs shamelessly tried to cash in on nostalgia by bringing in Cliff Fletcher who tore the team apart and got nothing for it. The goal was to break up the "Muskoka Five" and begin the rebuild. Here's what he did:
Alex Steen and Carlo Colaiacovo traded for Lee Stempniak.
Darcy Tucker bought out after an 18 goal season.
Pavel Kubina for Garnet Exelby and... I want to say a fourth liner that never played for Toronto?
Bryan McCabe and a fourth for Mike Van Ryn.
He traded two solid veteran defenseman and their top young player for a whole lotta nothing. Couldn't get any picks or prospects. Couldn't even get a late pick for Tucker.
The McCabe deal was especially bad. While he was one of the higher paid defenseman in the league, he wasn't far removed from finishing third in defensive scoring. He brought physicality, leadership and a slapshot that could punch a hole in a battleship if he could get it on target. And the Leafs came away with 27 games of Mike Van Ryn.
For a team that had zero blue chip prospects, this was a horrific way to kick off the rebuild. Between Fletcher trading away established veterans for nothing and Ferguson trading away futures for over-the-hill rentals, it led to a period of mediocrity that took the combined efforts of four GMs (Burke, Nonis, Lamoriello and Dubas) to eventually crawl out of.
And still the team can't win. I hate being a Leafs fan.