20 years ago today marked the start of one of the worst eras in Maple Leafs history

Some of the darkest days in Maple Leafs history occurred under Ferguson's reign. He was, of course, responsible for the infamous Tuukka Rask for Andrew Raycroft trade. He was also responsible for trading a 2007 1st-round pick (which became Lars Eller), a 2007 2nd-round pick (which became Aaron Palushaj) and a 2009 4th-round pick (which became Craig Smith) to San Jose for goaltender Vesa Toskala and forward Mark Bell. Certainly a couple of questionable decisions, but there were more where that came from.

JFJ was responsible for inking veteran forward Jason Blake to a 5-year contract in 2007. The move came just one season after Blake had broken out and scored 40 goals as a member of the New York Islanders. Needless to say, he never reached those heights again, scoring a combined 50 goals across 3 seasons in Toronto before being traded to Anaheim during the 2009-10 season.

Another controversial decision that Ferguson made was when he fired Pat Quinn, arguably the best Maple Leafs head coach in the last 30 years. The Leafs were 300-196-52-26 in 574 games under Quinn. He also led the team to a pair of Conference Finals appearances in 1999 and 2002. At the time, there was believed to be a difference in philosophy between Quinn and Ferguson. Naturally, you're never going to win an argument against your boss, and Ferguson had no qualms with parting ways with Quinn as a result. We all know how that worked out.

In the end, there weren't many things to celebrate under JFJ. His tenure as Leafs GM created a lot of lasting memories for a lot of the wrong reasons. I remember him today not to celebrate anything he did during his time in Toronto, but rather as a reminder that things can always be worse than they are right now, even with all of the recent playoff struggles.