Which of these Leafs trades would you go back in time and stop from happening?

[LeafsNation75]

Knowing what we know today if you could go back in time and stop the Leafs management from making a trade which one of these would you want to prevent from happening?

1) Toronto acquires Owen Nolan from San Jose on March 5, 2003 for Brad Boyes, Alyn McCauley and a 2003 1st round pick.

2) Toronto acquires Lee Stempniak from St. Louis on November 24, 2008 for Alex Steen and Carlo Colaiacovo.

3) Toronto acquires Phil Kessel from Boston on September 18, 2009 for a 2010 1st round pick, 2010 2nd round pick and a 2011 1st round pick.

I guess you can say there is a case that if all three of trades could be undone we would say yes based on the players they gave up or the draft picks they turned into. However if I had to pick just one I would not do the trade for Owen Nolan. I know they were a legit Stanley Cup contender at that time and I was all for the trade when it happened. However looking back at who the Leafs could have selected in the 1st round of the 2003 draft makes me think what if they kept that pick? Although that's assuming they get Corey Perry, Ryan Getzlaf, Zach Parise or Ryan Kesler.

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[jaric1862]

Kessel trade

 

[WilliamNylander]

Phil

 

[KGL]

The Rask trade.

 

[Punch Drunk Loov]

1. All bad
2. Phil Kessel
3. Trade not mentioned

 

[tmlfan98]

The Kessel trade was only bad in hindsight and the Nolan trade was made while we were still contenders. The Stempniak trade was bad from the start.

 

[SprDaVE]

Why do you guys do this to yourselves?

 

[LeafalCrusader]

Kessel trade by far

-I'd bet the Leafs would find a way to pick the dud in that 03 draft.
-Steen I'm not sure would have ever been the same player here developing under Wilson and Carlyle as he was in St.Louis. Still hate that trade though

-But the Kessel trade really killed us. Take away Kessel's goals from those teams and we're likely getting 2 top 5 picks.

Edit didn't see the other option. Rask trade then. That was even worse lol

 

[Loosie]

Rask for Raycroft.

 

[IBeL34f]

The Rask trade.

Was gonna say, this should replace the Nolan deal.

With Rask in net when Burke comes on board, I don't think the Kessel trade works out nearly as bad for us.

I'll probably still say the Kessel deal though. It's frustrating, cause I think he was pretty awesome for us for a time, but he represents a bleak period of modern Leafs history, and the value we shipped out to acquire him is a big part of that. If I had to pick between Seguin + Hamilton, Rask, or Steen to put on this team right now, I definitely pick option A, and I think that alone is sufficient enough to answer this one.

 

[pspot]

as much as the Kessel trade pains me if everything else the same (current management group and prospects and picks) i'd have to think adding Rask back in to the fold would be the greate impact

 

[saltming]

They were all bad but ot lottery protecting the kessel pick was legenday idiocy.

 

[tmlfan98]

The Rask trade.

Rask for Raycroft.

The Rask trade just like the Kessel one was only bad in hindsight. Pogge was considered the better prospect at the time.

 

[Jimmy Firecracker]

Why do you guys do this to yourselves?

All Leafs fans are masochists don't y'know? I'm pretty sure it's a requirement.

 

[7even]

Rask for Raycroft. We had some bubble teams that an elite goalie could've pushed over the edge. I actually think the entire landscape of this team would be different.

 

[IBeL34f]

The Rask trade just like the Kessel one was only bad in hindsight. Pogge was considered the better prospect at the time.

There were plenty of people who were skeptical (at best) of those trades when they originally went through. The risk of the Kessel deal hung in the air the moment it was announced.

Hindsight makes it worse, but there were questions surrounding them when they happened as well.

Neither of them made my stomach immediately sink the way the Steen trade did though. I gave the others some time to play out, but that one felt bad from the start.

 

[LeafsNation75]

The Rask trade.

I just knew there would be one more trade I forgot to add onto the list in it's own category.

 

[IBeL34f]

Rask for Raycroft. We had some bubble teams that an elite goalie could've pushed over the edge. I actually think the entire landscape of this team would be different.

This is why I'm not a massive fan of topics like this. We went through plenty of pain, but it's led to this point where we finally seem to be on the right track. I think I prefer the extra pain for a future led by Shanny and Babcock than I would if JFJ or Burke had been successful in their attempts. And this is coming from someone who appreciated Burke's efforts while he was here.

 

[Gary Nylund]

The Steen trade was nuthin'. Guys like me remember stuff like:

Trading for Tom Kuvers.

Trading Lanny Macdonald.

Trading Darryl Sittler.

That'll do for a start.

 

[Stephen]

The Kessel trade without a doubt.

 

[yubbers]

Why do you guys do this to yourselves?

 

[Buds17]

The Rask deal (and the aftermath). It was everything that could go wrong - Rask becoming a starter was tough, Raycroft not doing well as a Leaf didn't help, but that all might've been forgotten if Pogge panned out.

 

[Marmoset]

The Kessel trade was only bad in hindsight....

A lot of people disagree with that, myself included.

The main reasons we would cite:
1. It was the wrong point in time for the team to make that kind of trade, sacrificing high picks for one young player with a lot of question marks.
2. Trading those first rounders was a big risk. It's not like they were coming off a successful playoff run. It's true that Burke severely overestimated the quality of the team and did not expect to give up such high picks - but MANY other fans, analysts, etc. did not share his optimism about that roster.

That's all on that, not going to keep rehashing this. I just don't understand the hindsight argument for the Kessel deal when so many people saw it coming right from the start.

 

[diceman934]

The Steen trade was nuthin'. Guys like me remember stuff like:

Trading for Tom Kuvers.

Trading Lanny Macdonald.

Trading Darryl Sittler.

That'll do for a start.

Yes....I will add:

Kehoe
Carlyle

And Murphy for nothing to Detroit and we paid a 3rd of his contract

 

[diceman934]

A lot of people disagree with that, myself included.

The main reasons we would cite:
1. It was the wrong point in time for the team to make that kind of trade, sacrificing high picks for one young player with a lot of question marks.
2. Trading those first rounders was a big risk. It's not like they were coming off a successful playoff run. It's true that Burke severely overestimated the quality of the team and did not expect to give up such high picks - but MANY other fans, analysts, etc. did not share his optimism about that roster.

That's all on that, not going to keep rehashing this. I just don't understand the hindsight argument for the Kessel deal when so many people saw it coming right from the start.

It was a horrible trade from the hop....by one of our worse ever GM's