Ghosts of Leafs trades past haunting playoffs

Anaheim Ducks Rickard Rakell (67) celebrates his game winning overtime goal as Winnipeg Jets' Jacob Trouba (8) looks on, during game three NHL playoff hockey action in Winnipeg, Monday, April 20, 2015. (Trevor Hagan/CP)

The Winnipeg Jets’ first Stanley Cup Playoff game since 1996 grabbed the attention of the hockey world last night — myself included.

I’m not a Jets fan and I don’t dislike the Ducks. But I have to admit, I would have preferred for the Jets to win. I just like happy fans and a good story, and a Jets win would have given us both. Unfortunately for Jets fans, that was not in the cards. The Anaheim Ducks scored in overtime. Specifically, Rickard Rakell scored in overtime.

Rickard Rakell.

That name always stings me as a Leafs fan. Why? Join me on a journey down the Maple Leafs trade rabbit hole.

In 2011, the Leafs traded Tomas Kaberle to the Boston Bruins for a first round pick, a conditional 2nd round pick, and Joe Colborne. It looked like a three-way win: The Bruins got their Stanley Cup, Kaberle got his Stanley Cup, and the Leafs got three very valuable assets for their rebuild du jour. The deal looked fantastic for the Leafs at the time.

“Assets” is the key word there. A scout by the name of Gus Katsaros taught me a very valuable term in hockey several years ago: Asset management. This trade by the Leafs is a prime example of abysmal asset management and, frankly, it’s probably part of the reason Shanahan and company decided to fire Dave Nonis and 18 scouts.

The first rounder

The first round pick the Bruins gave up to the Leafs ended up being the best-case scenario for Boston: 30th overall. (Pays to be the champs, eh?) No matter for the Leafs, though — that’s still a valuable pick. Unfortunately for Toronto, 30th overall wasn’t quite good enough. The Leafs had their eyes on a young whippersnapper out of the U.S. by the name of Tyler Biggs and word on the street was that Biggs wouldn’t still be available by the 30th pick. The Leafs took action and traded the the 30th overall pick (Boston’s first) and the 39th overall pick (Toronto’s second) to Anaheim in exchange for the 22nd pick overall. Tyler Biggs gets drafted by Toronto and the Leafs get their man.

The Ducks selected Rickard Rakell with the 30th pick. Ouch, right? Allow me to rub salt in that wound: The Ducks selected John Gibson with the 39th pick. Tyler Biggs? Well, he had five points in the AHL this season.

Did I mention that Rickard Rakell’s number is 67? Rickard Rakell’s number is 67. Very funny, Rickard.

The conditional second round pick

The condition on the second rounder the Leafs received from Boston hinged on the Bruins making the 2011 Stanley Cup Final. They did, so the Leafs were awarded Boston’s second round pick for the 2012 NHL Entry Draft the following year.

Leafs management decided to trade this pick to the Colorado Avalanche for John-Michael Liles. Again, it seemed like a good idea at the time. As time and injuries wore on, the Leafs soured on Liles and his contract — that the Leafs signed him to, by the way — so it was time for a trade. On the day of the 2014 Winter Classic, the Leafs traded Liles to the Carolina Hurricanes in exchange for Tim Gleason. If CapGeek was still online, you might know Gleason better as one of the guys the Leafs are currently paying not to play for them because of a buyout.

Oh, it gets better.

Joe Colborne

With one-way contracts like Colton Orr and Frazer McLaren, the Leafs decided to trade Colborne rather than have him as a healthy scratch. He was dealt to the Calgary Flames in exchange for a fourth round pick in 2014.

Who did the Leafs draft with this pick? They didn’t. They traded that pick to the Blues in the trade that brought Roman Polak to Toronto. Now Polak is one of the many names rumored to be on his way out of town.

And I thought of all of this nonsense just because Rickard Rakell went and scored an overtime winner in the Stanley Cup Playoffs. It’s OK though, I won’t torment you anymore, Leafs fans…

ACTUALLY if you’ve got a second, there is one more trade I was reminded of during this game.

The MTS Centre exploded when Lee Stempniak scored the Jets’ first Stanley Cup Playoff goal since 1996.

Lee Stempniak.

There’s another name that stings Leafs fans. By now we all know the abomination that was Alex Steen and Carlo Colaiacovo for Lee Stempniak deal. What if I told you it gets worse?

After parts of two seasons in Toronto, Lee Stempniak was traded to the Phoenix Coyotes in exchange for a defender named Matt Jones, as well as fourth and seventh round picks in 2010. Three assets! Not bad. What did the Leafs do with them?

Matt Jones

After several minutes of super-thorough Google research, I can’t find anything on Matt Jones beyond the 2008-09 season. I’ll assume he was included in this trade just to free up a roster spot.

Phoenix’s 2010 seventh round pick

The Leafs traded this pick to Edmonton in exchange for the Oilers’ sixth round pick in 2011. The Leafs drafted Dave “Brolldozer” Broll with that pick. Broll was recently traded to Tampa Bay along with Carter Ashton in exchange for a conditional seventh round pick. Nothing much there but at the end of the day, it’s pretty rare to get much value for a seventh-rounder. This next pick is the fun one.

Phoenix’s 2010 fourth round pick

The Leafs didn’t keep this pick. Are you noticing a trend here? The Capitals wanted to move up so they traded their fourth and fifth round picks (116th and 146th overall) to Toronto for this pick (112th overall).

The 116th pick turned into Petter Granberg, who has played eight career NHL games so far. The 146th pick turned into Daniel Brodin, who isn’t exactly lighting it up in Sweden as a winger.

Who did the Capitals get with the 112th pick? Goaltender Philipp Grubauer, who recently picked up the Game 2 win for Washington in their series versus the New York Islanders. Fun!

I’m not bringing these things up to be going “Leafs, Leafs, Leafs!” (I may be a Leafs fan but trust me when I say I don’t want to talk about this hockey team right now.) I’ve been looking to escape their brutal season by watching other teams beat the hell out of each other with some good, old-fashioned playoff hockey.

But Rakell. Stempniak. Colborne. Grubauer. Every way I turn, I’m haunted by the ghosts of Leafs past.

When submitting content, please abide by our submission guidelines, and avoid posting profanity, personal attacks or harassment. Should you violate our submissions guidelines, we reserve the right to remove your comments and block your account. Sportsnet reserves the right to close a story’s comment section at any time.