The once highly debated joke of a front office are winners even though the team they’ve put on the ice is the worst in the league.

When the front office, along with head coach Mike Babcock, promised Toronto Maple Leafs fans that the rebuild would be painful, they weren’t kidding.

Although Toronto is doing a great job going for the number one overall pick in this June’s NHL Draft, the team are winners following the NHL trade deadline which took place on Monday.

Since the Dion Phaneuf trade at the beginning of February, the Leafs made four more deals, which made them overall winners following the deadline.

The Deals

Toronto got things started back on Feb. 9, when they dealt Phaneuf to the Ottawa Senators in a nine-player trade.

Toronto sent defensemen Phaneuf, Cody Donaghey, along with forwards Matt Frattin, Casey Bailey, and Ryan Rupert to Ottawa for defenseman Jared Cowan and forwards Milan Michalek, Colin Greening, Tobias Lindberg, and a 2017 second-round draft pick.

There wasn’t another trade in the NHL until Toronto made headlines on Feb. 21, when they sent forward Shawn Matthias to the Colorado Avalanche for forward Colin Smith and a 2016 fourth-round draft pick.

Raffi Torres during his time with San Jose Sharks in September 29, 2015 / Rocky W. Widner - NHL/Getty Image
Raffi Torres during his time with San Jose Sharks in September 29, 2015 / Rocky W. Widner - NHL/Getty Image

One day later the trading continued as Toronto sent defenseman Roman Polak and forward Nick Spaling to the San Jose Sharks for forward Raffi Torres and a second round draft-pick in 2017 and 2018. Torres was then loaned to the Sharks AHL affiliate for the remainder of the season.

That wouldn’t be the last deal between Toronto and San Jose. Toronto sent goaltender James Reimer and forward Jeremy Morin to San Jose for goaltender Alex Stalock, forward Ben Smith and a conditional fourth-round draft pick in 2018.

In the last deal the Leafs sent forward Daniel Winnik and a fifth-round draft pick in 2016 to the Washington Capitals for forward Brooks Laich, defenseman Connor Carrick and a second-round draft pick in 2016.

After the Fact

The Leafs were no doubt going to be sellers all season long. It was clear trades would be made at the deadline or throughout the season when the team signed many players to one-year deals in free agency.

Since the team is in the midst of a rebuild, draft picks are extremely valuable to have and Toronto now owns over 10 draft picks.

James Reimer of the Toronto Maple Leafs faces a shot in the warm-up prior to play against the New York Rangers in an NHL game at the Air Canada Centre on February 18, 2016 in Toronto, Ontario, Canada. The Rangers defeated the Maple Leafs 4-2 / Claus Andersen - Getty Images
James Reimer of the Toronto Maple Leafs faces a shot in the warm-up prior to play against the New York Rangers in an NHL game at the Air Canada Centre on February 18, 2016 in Toronto, Ontario, Canada. The Rangers defeated the Maple Leafs 4-2 / Claus Andersen - Getty Images

The most questionable trade made has to be the James Reimer deal. The goaltender was traded along with forward Jeremy Morin were given up for goalie Alex Stalock, forward Ben Smith and a conditional draft pick.

Stalock was immediately sent to the minors and Reimer alone was believed to have been worth at least a second round draft pick. This trade alone is the most questionable of them all but because of Reimers efforts with the Leafs over the years, many are happy that the net minder will now have an opportunity to win somewhere else. 

Jared Cowen who was acquired in the Phaneuf trade, will reportedly be bought out and become a free agent. The team tried to trade the defenseman at the deadline but could not find a team willing to make a deal. 

The moves prior to the deadline look promising for Toronto. Now that they are able to bring up many of their prospects they can now see how they are progressing and will have a better idea of what they have with them.

The fact the Leafs were able to dump contracts and gain draft picks are crucial in the midst of a rebuild.

Toronto is amongst the winners at the trade deadline. This past deadline will be looked upon as one of the more successful ones Toronto has had in many years and if things are done right at the draft, and if the rebuild is successful, it can be one of the key reasons behind it.