Post 2005/2006: Top 5 worst contracts given

bobholly39

Registered User
Mar 10, 2013
22,477
15,288
some names mentionned I'll comment on...

Dipietro doesn't belong. Contract was fine - issue was he got injured. If he had been healthy, good chance he has a strong career and ends up underpaid

PLD doesn't belong. 1 year is too soon to judge. Maybe he makes the list eventually, but not yet

One name I'll mention - Bobrovsky. A year or two ago he seemed well on his way to top these conversations - so it's an absolute fantastic and unexpected turnaround he's had lately. Figured it was worth calling out.

I don't know if it's the absolute worst contract based on total $$ value - but one that always jumped out at me as absolutely terrible was Lucic. Such a hateable player too, which just adds to it.
 
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Empoleon8771

Registered User
Aug 25, 2015
81,762
79,925
Redmond, WA
I think some of the posts in here have some major recency bias, I wouldn't put someone like Jeff Skinner anywhere even close to this conversation.

DiPietro and Bryzgalov are absolutely 2 of the worst deals, especially when you look at a cap% value. DiPietro's $4.5 million AAV deal signed in 2006 was 10.23% of the cap, which is equivalent to an $8.5 million cap hit this year. Same thing with Bryzgalov, his deal was about equal to $7.35 million AAV with today's cap. Considering the cap%, massive term and horrible performance under those deals, both of those two are firmly 2 of the 5 worst.

My rankings would be:

1. DiPietro
2. Gomez
3. Drury
4. Redden
5. Clarkson
6. Bryzgalov

I know the rankings only asked for 5, but I didn't want to not include any of these guys. Clarkson sticks out as not being nearly as high of a cap hit% as the other guys, guys like Redden, Drury and Gomez were making the equivalent of $10+ million in today's money while Clarkson was only around $6.5 million. But Clarkson was so heinously bad the second he signed that deal that I can't not include it.
 

Little Bobby Boo

Registered User
Jul 30, 2014
3,408
3,420
While not the absolute worst, Dave Bolland 5x5.5M with Florida was dreadful. Atleast he was LTIRed for them.


View attachment 866510
traded to AZ with Crouse for a second and a third, both of which Tallon struck out on. Just a brutal contract the day it was signed.
 

Ligue

Registered User
Sep 28, 2017
116
174
The contract wasn’t horrible at the moment of signing but not enough mentions of Vincent Lecavalier here. Dude is still getting an nhl salary.
 

MCR74

Registered User
Nov 11, 2022
3,194
3,484
Travis Green just got a four year head coach gig with the Sens. Does that count?
 

Nick Hansen

Registered User
Sep 28, 2017
3,127
2,658
It's not the worst deal ever but Toews' contract really turned into an annoyance quite shortly after it was signed. It's a shame because his reputation took quite the hit from it. He was an excellent player up until 26-27 or so but age and the contract on top of it just really hit him badly.
 
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GreeningOil

Yarpmeister
Jun 22, 2016
2,991
3,515
Saskatoon
Off the top of my head:
David Clarkson (Leafs were lucky to get out of this one)
Ilya Bryzgalov (Flyers were lucky to have compliance buyouts)
Jeff Skinner
Andrew Ladd
Marc-Edouard Vlasic

HM: Lucic, Nurse, Campbell, Huberdeau (may be #1 after next season), Josh Anderson
At least Nurse plays big minutes in a good team. (Still not great)

Campbell contract is ultra horrible.

And then, there is a new level for Hunerdeau
 

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