With the 2020 NHL Trade Deadline coming up in a few days, the Toronto Maple Leafs have some thinking to do about how they want to take advantage of the cap space they have for the remainder of the season.

Maple Leafs have cap space to spend, but do they have the assets?

While it’s good to use your assets when you can to improve your team, sometimes things down’t always go the way you want them. I’m here to be the negative voice leading up to the trade deadline, and warn everyone of the horrors that could fall upon us. Come, join me on this journey.

Note that when I say “Trade Deadline Deal” I’ll be referring to trades that took place in the last two weeks ahead of the deadline.

March 2nd, 2010
To Toronto: Luca Caputi, Martin Skoula
To Pittsburgh: Alexei Ponikarovsky

The Expectation: Good assets in exchange for a departing UFA.
The Reality: The opposite of that.

When I was looking up this trade, none of the articles written about it had quotes from Leafs GM Brian Burke about the move. I couldn’t find any reason in Ponikarovsky’s stat line about why the Leafs would move on from him - he had 41 points in 61 games that season with the Leafs - so it was just a case of getting what you could for a pending free agent you’re not re-signing.

Coming to Toronto was Luca Caputi, a 2007 4th round pick for the Penguins and journeyman defender Martin Skoula. Skoula would be flipped the next day to the New Jersey Devils in exchange for a 2010 5th round pick (Sam Carrick), and Caputi would play 25 total games for the Leafs until he was traded to the Anaheim Ducks mid-season in 2011-12 for Nicolas Deschamps, who would be flipped for Kevin Marshall who would leave the Marlies for Sweden. Sam Carrick would be released following his entry-level contract, and is currently playing in the Ducks organization.

Overall this trade wasn’t a complete bust, but I wouldn’t call it a win either.

February 7th, 2008
To Toronto: Yanic Perreault, 2008 5th round pick
To Arizona: Brendan Bell, 2008 2nd round pick

The Expectation: A face-off specialist to help the Leafs out in their first playoff run since the cancelled season.
The Reality: The Leafs would give up a pick that became a top tier defender in exchange for missing the playoffs by 11 points.

I remember where I was when this trade broke. I was driving back from Ikea in Etobicoke while on my lunch break with a co-worker, and we were on the Gardner listening to 590. This trade was being sold as a positive because Perreault was a faceoff specialist the Leafs would need heading into the playoffs. Bell was a 2001 third round pick, who was in his first full NHL season but couldn’t crack another roster, and he finished his career bouncing between the AHL and Europe.

What makes this a terrible trade was the draft picks involved. The Leafs would use that 5th round pick on Joel Champagne, whose main contribution to the Leafs was this stupid thread.

The biggest travesty of this trade comes in hindsight because the Coyotes would send that second round pick to the Nashville Predators, who would use it to select Roman Josi who is....yep, pretty good. He even made my team of traded draft pick players.

The Traded Draft Picks All-Star Team

March 11th, 2003
To Toronto: Doug Gilmour
To Montreal: 2006 6th round pick

The Expectation: A Maple Leafs hero returns to help the team fight for its first Stanley Cup in 37 years.
The Reality:

This wasn’t a terrible trade, the 6th rounder became Mark Flood who would be a career minor leaguer. It’s terrible because it resulted in a Maple Leafs legend and Hall of Famer player’s career ending with him crawling on his hands and knees off the ice.

March 13th, 2001
To Toronto: Aki Berg
To Los Angeles: Adam Mair, 2001 2nd round pick

The Expectation: A big bodied player to help the Leafs survive the rough games of the playoffs.
The Reality: The Leafs give up a steady third line centre and the pick that became Mike Cammalleri in exchange for a fourth liner and no Stanley Cup.

This is another one that focuses on the draft pick traded away more than anything else. Cammalleri was a 50-80 point player for the first six seasons of his career, from 2005-2011, a time period that the Maple Leafs could have really used another high end forward.

March 13, 1996
To Toronto: Wendel Clark, Mathieu Schneider, DJ Smith
To NY Islanders: Sean Haggerty, Darby Hendrickson, Kenny Jonsson, 1997 1st round pick

To Toronto: 1996 2nd round pick, 1998 4th round pick
To New Jersey: Dave Andreychuk

The Expectation: Owner Steve Stavro saves some money to pay off his debts
The Reality: A trip down memory lane with Clark, and the Islanders got to draft someone else’s Hall of Fame goalie. Oh, and Stavro didn’t pay off his debts.

The Leafs were clearing out the roster as Stave Stavro struggled to keep his outside businesses afloat. Andreychuk wasn’t a 99-point player like he was in 1994, but he was a solid veteran player on many teams after this trade, until he would win his first Stanley Cup with the Tampa Bay Lightning. Kenny Jonsson was an excellent defender who can be added to the long list of players who the Leafs gave up on too soon.

Schneider was a good defender, DJ Smith was a minor-leaguer, and Wendel Clark was good in 96-97, but those 65 games would be the most he’d play in a season for the rest of his career. The real kicker in this trade was the first round pick the Leafs sent to Long Island - it would be used to pick future Hall of Famer Roberto Luongo.

The deadline hasn’t been a great time for the Leafs to make a deal, so just know that if the Leafs trade a draft pick it will become the next Nikita Kucherov.

Enjoy the trade deadline coverage folks!