Worst recent trade involving a future high 1st round pick (Seguin, Duchene, Karlsson)

[Gains]

Three recent trades involving a future high 1st round pick come to mind. By that I mean a trade where a team acquires an established player for their 1st round pick, then has a bad regular season(s).

I am asking you which trade you think is the worst for the team acquiring the established player. You have to consider that the team knew beforehand which lottery format was used. Also consider how the team was playing before the trade. If you don't consider any of those trades to be bad, it's fine, just pick the worst between the three.

For Toronto :
September 18, 2009: Kessel traded to Toronto by Boston for Toronto's 1st (Tyler Seguin) and 2nd (Jared Knight) round picks in 2010 NHL Draft and Toronto's 1st round pick (Dougie Hamilton) in 2011 NHL Draft. Toronto finished 2nd to last in the 2009-10 season.

Phil Kessel

1st-round pick in 2010 1st-round pick in 2011 2nd round pick in 2010

[TBODY] [/TBODY]

For Ottawa:
November 5, 2017: Duchene traded to Ottawa by Colorado as part of a three team deal in which Ottawa sent Kyle Turris to Nashville, Andrew Hammond, Shane Bowers, Ottawa's 1st round (protected) pick in 2018 NHL Draft and Ottawa's 3rd round pick in 2019 NHL Draft to Colorado and Nashville sent Samuel Girard, Vladislav Kamenev and Nashville's 2nd round pick in 2018 NHL Draft to Colorado. Ottawa finished 2nd to last in 2018 and last in 2019.

Matt Duchene

Kyle Turris Shane Bowers Andrew Hammond conditional 1st-round pick in 2018 or      1st-round pick in 2019 3rd-round pick in 2019

[TBODY] [/TBODY]

For San Jose:
September 13, 2018: Karlsson (along with Francis Perron) was traded to the San Jose Sharks in exchange for Chris Tierney, Dylan DeMelo, Josh Norris, Rūdolfs Balcers, the Sharks' first-round pick in 2020, second-round pick in 2019 and a conditional second-round pick in 2021. San Jose finished 3rd to last in 2020.

Erik Karlsson Francis Perron

Chris Tierney Dylan DeMelo Josh Norris Rudolfs Balcers conditional 1st-round pick in 2019* or      1st-round pick in 2020 conditional FLA 2nd-round pick in 2019 or      SJS 2nd-round pick in 2019 conditional 1st-round pick in 2021 or      2nd-round pick in 2021 conditional 1st-round pick

[TBODY] [/TBODY]

* The condition – Ottawa will receive a first-round pick in 2020 if the Sharks qualify for the 2019 Stanley Cup playoffs – was converted on March 19, 2019.

EDIT:

Previous season stats:
2008-09 Toronto: 34-35-13 (81 points)
2016-17 Ottawa: 44-28-10 (98 points) Lost Conference Finals (4-3) versus Pittsburgh Penguins
2017-18 San Jose: 45-27-10 (100 points) Lost Second Round (4-2) versus Vegas Golden Knights

Click to read more...

 

[Rhaegar Targaryen]

Kessel. Seguin AND Hamilton

 

[Pokecheque]

What's funny about the Seguin/Hamilton deal was that the Bruins decided to fritter away those assets for next to nothing as well.

 

[CanadienShark]

Ottawa getting Duchene.

 

[The Macho King]

The Seguin trade should probably be on here.

 

[Merrrlin]

Ottawa giving up all that, while on the brink of a rebuild, then losing everything including Duchene is just horrendouse.

At least Toronto and San Jose get to enjoy the player they dealt for.

I am not sold on Byram though so I guess we will need to see. Losing Laf would be painful too, if that's how it goes down.

 

[JKG33]

As of now I'd say Toronto, because they managed to give up 2 high 1sts.

Ottawa had it rough in that they totally collapsed after acquiring Duchene, but they lucked outbid not winning the lottery.

Jury's still out on San Jose. If the pick wins the lottery then I'd say them quite easily. Even if it doesn't, its still not a good look giving up such a high pick and doubling down by signing Karlsson to that garbage contract. I'd be very surprised if he's worth the money for even one of those years

 

[The Jones Zone]

d) your really bored

 

[Dekes For Days]

Toronto probably should have gotten a goalie first, but Kessel was a good player, and they got 6 years of his prime and assets from trading him.
San Jose shouldn't have re-signed Karlsson to his ridiculous contract, but the price they paid wasn't outrageous for a big last shot at the cup.
Duchene trade didn't really make any sense at all, even at the time.

 

[DitchMarner]

Meh... I don't really care for Seguin. I'd rather have Matthews right now than TS (and I'm not a huge AM fan). Also, at least Kessel has had some productive post seasons.

Having missed out on Hamilton sucks, but I don't lose sleep over that trade.

 

[LeafsNation75]

Meh... I don't really care for Seguin. I'd rather have Matthews right now than TS (and I'm not a huge AM fan). Also, at least Kessel has had some productive post seasons.

Having missed out on Hamilton sucks, but I don't lose sleep over that trade.

Even though the 1st round picks Toronto traded turned into Tyler Seguin and Dougie Hamilton, it was Boston who ended up trading Seguin to Dallas and Hamilton to Calgary.

 

[Satoru Gojo]

I have no idea why Brian Burke thought giving 2 first rounds picks for Kessel was a good idea

 

[topshelf15]

Ouch if SJ would have made the finals and lost again....

 

[LeafsNation75]

I have no idea why Brian Burke thought giving 2 first rounds picks for Kessel was a good idea

The better question is do you believe Brian Burke that at the 2009 draft he thought Boston was going to trade them Phil Kessel and the 25th overall pick for Tomas Kaberle.

However the trade didn't go through because Boston thought Toronto was giving them Tomas Kaberle and the 7th overall pick Phil Kessel.

 

[Mickey Marner]

Karlsson is TBD. Kessel cost the most, but he was also a star. Matt Duchene is a loser and he always will be.

 

[NyQuil]

Duchene trade didn't really make any sense at all, even at the time.

We're kind of convinced that he was Dorion's white whale.

 

[topshelf15]

We're kind of convinced that he was Dorion's white whale.

His replacement for an out going Turris....But just a stupid money motivated trade anyway you slice it,much like Zbad trade...Money in for money out

 

[amnesiac]

Duchene considering hes already gone AND wouldve had Makar

I would be soooo pissed.

 

[NyQuil]

Duchene considering hes already gone AND wouldve had Makar

I would be soooo pissed.

Meh, when your team is a tire fire, you kind of get numb after awhile.

 

[Tryblot]

The better question is do you believe Brian Burke that at the 2009 draft he thought Boston was going to trade them Phil Kessel and the 25th overall pick for Tomas Kaberle.

However the trade didn't go through because Boston thought Toronto was giving them Tomas Kaberle and the 7th overall pick Phil Kessel.

Wasn't that Jeff carter?

 

[Meeqs]

This is actually a super interesting and difficult question. Primarily because each of these trade has a different degree of information around it, so how you go in with perspective changes it massively.

It is unlikely the return for the latter 2 ends up giving better players than Seguin + Hamilton, but do we evaluate that or the picks at the time of the deal? We also dont know how players like Byram will turn out or even who Ott will get with that high 1st.

Also we could look at what the return accomplished. Bos won a Cup with Segs so do they win because of that? How much do we value the return? Tor got a ton of good years out of Kessel while Ott got 1 season from Duchene? Do we factor in the returns from further trades?

So like I said its very fun. There are so many moving parts I would simply say the winner was the team that got the best player for the longest. So if Col gets 15 years of Byram on the top pair then they would win (also including Girard and Bowers could also be strong contributors). If Ott gets Laffy from the pick and he stays for his career and is simply the best player then I would say they would win.

Just fun. Well thought out post. The winners were the fans of those teams. Also mad props to Dorion for getting absolutely fleeced and turning it around to hit another GM with the same destruction that hit him.

 

[LeafsNation75]

Wasn't that Jeff carter?

That was when Cliff Fletcher was the Leafs interim GM during the 2007-08 season and he agreed to trade Kaberle to the Flyers for Jeff Carter. However Kaberle had a NTC and blocked the trade.

Although there was another clause in his contract at the time which said the following.

https://www.capfriendly.com/players/tomas-kaberle

CLAUSE DETAILS: Lists 10 teams he can be traded to if his team misses the playoffs in 2008-09 or 2009-10, he can be traded from the following entry draft until Aug. 15

That's why Brian Burke could have traded him at the 2009 draft for Phil Kessel without having to ask him to waive his NTC.

 

[jetsforever]

None were horrible but I guess the Ottawa one was worst for them since they didn't really get anything out of Duchene either.

 

[amnesiac]

Meh, when your team is a tire fire, you kind of get numb after awhile.

I hear ya, but after this draft I think youll be smiling a lot more.

 

[garbageteam]

Duchene, easily. Got almost nothing out of it. Way too early to call on Karlsson and the Leafs got some decent mileage out of Kessel, even if it didn't result in much. Compared to those Duchene in a landslide.