2007: Sitting just outside a playoff spot in late February, the Leafs opted to shore up their depth down the middle. They swung a trade to land Yanic Perrault (again) from Phoenix, surrendering a second round pick that later became Roman Josi, now on a top pairing with Shea Weber in Nashville.
2008: In his first summer (back) in charge, Fletcher fired Maurice and proceeded with two horrific signings. Jeff Finger, who had played one full season in the NHL, was signed for four years at a head-scratching $3.5 million per season. Finger was placed on waivers less than three years later, finishing his Toronto tenure in the AHL.
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Continuing an ugly trend of decisions made in an interim capacity that winter, Fletcher opted to send former first rounder Alex Steen (and Carlo Colaiacovo) to St. Louis for Lee Stempniak. Stempniak hadn't scored more than 20 goals in a few years and never has again. He was eventually traded to Calgary.
Steen, meanwhile, went on to great success as a Blue, scoring 33 goals last season.
2009: A few months after the Kessel trade, Burke parted with another first rounder, sending Jiri Tlusty to Carolina for Philippe Paradis. Tlusty evolved into a role player for the Hurricanes, Paradis still yet to make the NHL and is no longer part of the Leafs organization.
2010: The top pick that June (a second round selection), Brad Ross, was just suspended by the AHL, testing positive for a banned substance.
2011: Continuing a trend of awful free agent signings, Burke landed Tim Connolly from Buffalo on a two-year deal shortly after the draft. Connolly was mostly a ghost in one season as a Leaf, demoted to the Marlies the following year and yet to be heard from again.
2012: Carlyle talked about restoring respect to the Leafs brand, talked about turning the tides of a porous defensive team. It never happened. The Leafs ended a lengthy playoff dry spell under his watch, but were amongst the worst defensive teams in the NHL during his tenure.
He was fired earlier this month.
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While John-Michael Liles sat with a concussion, the club signed him to a four-year deal worth more than $15 million. Liles had played in less than 30 games as a Leaf (positively for the most part), but in spite of that short window, not to mention the concussion, the club decided to lock him up long-term.
They would quickly regret the decision. Liles never fit under the new head coach, was briefly assigned to the Marlies and then traded to Carolina for another bad contract. The Leafs then bought out that contract (Tim Gleason) and will have it on the books until the end of the 2018 season.
2013: Leiweke, who hadn't hired Nonis, handed him a five-year extension anyway.
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The freed up money [Note from Montresor: from Grabovski and Komisarek buyouts] was used to re-sign Tyler Bozak to a five-year deal and then David Clarkson to an exorbitant seven-year deal.
"If we wanted to get in on a player like David Clarkson, that was the price-tag for us to pay," Nonis said on the day of the signing. "I'm not worried about [years] six and seven right now. I'm worried about one [year] and year one I know we're going to have a very good player."
2014: The club announced the hiring of Brendan Shanahan as team president just a few short days after that fate became official. Shanahan was installed to lead a front office despite having never been involved in a front office of any kind before.