Top 10 Worst NHL Contracts: Rankings 1 to 5

I’ve already counted down half of the worst contracts currently in the NHL, and I know you all were eagerly awaiting my final five. Just to recap, there were three main criteria I judged these deals on:

  • How well a player did compared to their peers
  • If their performance justified their salary
  • Is the term of the deal manageable

These final five did poorly on each criteria, making me cringe each time I look at them.

So here they are, from bad to bad…est – the worst contracts in the NHL.

5) Ryan Miller, Vancouver Canucks – $6m AAV, UFA in 2017

Remember how I talked about the aging curve, and how it was not kind to hockey players in part one? Well, if it’s bad for skaters, it’s absolutely terrible for goalies, especially over 35. The Canucks signed Miller as a free agent – when he was already 34.

RMiller HD Sv Cap BandMiller Adj Sv Cap Band

Miller has been declining for a while. Last year he posted a 91.8% Adjusted Sv% – his lowest in 7 years. His highest in this timeframe came back in the 09/10 season. While it does follow my “no contracts over $18m for 30+ yr olds” edict, it’s still a vast overpayment, especially considering the kind of talent that was available at the time. Couple declining numbers with games lost to injury and the Canucks better hope their back up goalies are prepared for an increased workload.

4) Andrew MacDonald, Philadelphia Flyers – $5m AAV, UFA in 2020

This contract was probably the nail in the coffin of Paul Holmgren’s GM career. Strangely, MacDonald’s season in 13/14 was one of his worst, statistically, yet the Flyers saw fit to extend him for the next 6 years for a total of $30 million.

MacDonald FFRel Cap BandsMacDonald FA60 Cap Bands

One year in, this contract still looks like a bad idea. MacDonald is already 29, so it’s all likely downhill from here. At least he has one feather in his cap. After all, how many guys can say they were directly responsible for a front office shake up?

Update: Literally less than 24 hours after I wrote this piece, the Flyers placed MacDonald on waivers. Unsurprisingly, he’s expected to clear, with most teams taking an emphatic “pass” on this contract. With 2 of my picks now confirmed as terrible deals by their own teams, I’m starting to suspect someone’s spying on me.

3) Brooks Orpik, Washington Capitals – $5.5m AAV, UFA in 2019

Last summer when this contract was announced, the general reaction was “lol, ok, but seriously, what are the terms?” Slowly the laughter died as we realized the Capitals were serious. A clear violator of the $18m rule, this contract is the triumph of “experience” over common sense.

Orpik FFRel Cap BandsOrpik FA60 Cap Bands

I mean, at least it only has…four more years on it.

Sorry Caps fans. You have my sympathies.

2) Dave Bolland, Florida Panthers – $5.5m AAV, UFA in 2019

Bolland SCF Rel Cap Percent BandsBolland P60 Cap Percent Bands

No. Just…no.

1) Dion Phaneuf, Toronto Maple Leafs – $7m AAV, UFA in 2021

How could anyone have ever predicted this would turn out poorly? How? It’s not like he was already underperforming on a 6 year $6.5m AAV contract before he signed this current one.

Phaneuf FFRel Cap BandsPhaneuf FA60 Cap Bands

Listen, I am well aware that no one defender is responsible for a team’s entire defense being terrible, but Phaneuf is being paid the same as guys like Erik Karlsson. Erik Karlsson’s numbers, especially his relative ones, do not look like that. While the Leafs are finally making moves to right a sinking ship, they’re going to have a hard time trying to move this deal.

This is what it boils down to for the Leafs: trade Phaneuf or finally admit they’re paying #1 Defenseman salary to a 2nd pairing guy and move him to a position where he can be more successful. And that’s why Phaneuf holds down my top spot of worst active contracts – he was already overpaid BEFORE he signed this deal.

Written by Carolyn Wilke, who can be found on twitter @Classlicity