When casually taking a stroll down CapFriendly, an NHL analyst's version of taking a random walk down Wall Street, it's generally pretty easy to pick out each team's worst contract. Typically, that deal will belong to an aging member of the organization's core who once stood as a pillar of its success.

Some contracts age more gracefully than others, of course. How often do we see these human beings compared to wine?

Consider the Chicago Blackhawks' deals for Patrick Kane and Jonathan Toews. On July 9, 2014, when these matching megadeals worth $84 million over eight years were announced, it seemed like both forwards were on similar trajectories.

Kane and Toews were key pieces for a Blackhawks team that spent a solid decade flirting with becoming a dynasty. One could argue that Chicago actually was one, and we wouldn't quibble.

As important as both forwards have been in the Windy City, their contracts haven't quite aged the same.

Toews is only three seasons removed from scoring 81 points in 82 games, but after sitting out the entirety of 2020-21 because of "chronic immune response syndrome," it's fair to wonder what the 33-year-old has left in the tank. His health is obviously the primary concern here, but out on the ice, Toews might not be able to live up to his $10.5 million cap hit over the next two seasons.

Meanwhile, Kane has been a point-per-game player over the past three seasons, finishing 2020-21 tied for fifth in scoring. Kane turns 33 in November, illustrating just how differently two identical contracts can play out over time.

All of this is to say that NHL teams and players don't agree to contract terms in a vacuum. There are multiple angles to consider, especially when we have hindsight at our disposal.

 

Anaheim Ducks: Cam Fowler

Year Signed: 2017

Seasons Remaining: Five

Cap Hit: $6.5 million

A recent trend has seen NHL teams jump at the opportunity to lock up their young, up-and-coming defensemen. Over at The Athletic, Pierre LeBrun recently broke down the unique financial landscape that is encouraging players and organizations alike to commit to long-term deals.

Younger defenders have seemingly been signing eight-year extensions every third day over the past few months.

When the Anaheim Ducks and Cam Fowler agreed to terms on this eight-year pact, it made sense on many levels. He was coming off of his age-25 season, had already appeared in nearly 500 games and broken the 30-point barrier in three of the previous four campaigns. The Windsor, Ontario, native had draft pedigree, going 12th overall in 2010, and the $6.5 million cap hit seemed like a safe bet for the Ducks.

While Fowler hasn't exactly fallen off of a cliff in terms of his play, his production has dwindled in each season since the deal began in 2018. He was particularly bad in 2020-21, with an expected-goals-for percentage of 36.5.

Sure, the Ducks aren't a great hockey team right now, but Fowler hasn't been part of the solution for Anaheim. His cap hit isn't unmanageable, but he's entering his age-30 season, and the defenseman isn't likely to be worth $6.5 million for the next half-decade.

 

Arizona Coyotes: Clayton Keller

Year Signed: 2019

Seasons Remaining: Seven

Cap Hit: $7.15 million

It's here with the Arizona Coyotes that we first need to make this distinction: "worst" doesn't necessarily mean bad or hopeless for all of these teams. It just means that, as the rosters are constructed, these individuals are the ones who haven't been able to or are the most likely to underperform relative to their cap hits.

Enter Clayton Keller, who has just started his age-23 season. While he isn't a $7.15 million player yet, the Coyotes took a calculated risk on the former seventh overall selection by skipping a bridge deal entirely. After all, these are the kinds of players rebuilding teams need to lock down at reasonable cap hits.

That's what Arizona did with Keller.

The forward had an outstanding rookie campaign, posting 65 points in 82 games in his age-19 season, finishing third in Calder Trophy voting. From a points-per-60 perspective, Keller has taken a step back since then.

In his first year, he produced 3.2 points per 60. Over his past two seasons, Keller has been putting up points at a lower 2.3-per-60 clip. Those are solid numbers, but his production has fallen short of the expectations that come along with a cap hit north of $7 million.

He's one of just a handful of legit NHL talents on the league's most stripped-down roster, however. If Arizona can rebuild over the next few years, Keller will have more talent around him and should be able to grow into his contract.

 

Boston Bruins: Charlie Coyle

Year Signed: 2019

Seasons Remaining: Five

Cap Hit: $5.25 million

The Boston Bruins ice one of the most well-constructed rosters in the NHL. Their core is starting to age a bit, so they aren't in the shape they were two or three years ago. But Brad Marchand and David Pastrnak are on two of the best deals in the sport, while almost everyone else on the roster is at least supplying average value retaliative to their cap hits. No cap sheet is blemish free, though, and in Boston, said pockmark is Charlie Coyle.

On paper, Coyle looks like the kind of player who has traditionally been associated with the Bruins. He's big, plays hard and isn't easy to knock around in the offensive zone.

That's why it made a lot of sense when the Bruins traded for the former San Jose Sharks first-round pick in February 2019. The contract he signed ahead of 2020-21 made a bit less sense.

Players are worth more to teams than simply how many points they can put on the board, especially in Boston, where the team's vaunted first line is arguably the best in the NHL. Coyle is making a lot of money to post just 0.31 points per game, though. The Bruins' expected goals for/against also took a hit when the forward was on the ice in 2020-21.

It's tough to use that truncated season—the majority of which was played without fans in arenas—as a barometer, but as he enters his age-29 season with half a decade left on his deal, it's fair to wonder whether Coyle will ever be worth north of $5 million to the B's.

 

Buffalo Sabres: Jeff Skinner

Year Signed: 2019

Seasons Remaining: Six

Cap Hit: $9 million

Sometimes teams go off the rails for reasons that are hard to figure out. Hockey is, by and large, a game that is heavily influenced by random events that are difficult to control.

Still, when organizations are bad for as long as the Buffalo Sabres have been, there's a reason for it. It starts at the top, with consistently poor decision-making by the front office trickling its way down on to the ice on a nightly basis.

Case in point: Jeff Skinner.

The Sabres traded for him, bolstering their forward core in the process. He clicked with (former) franchise center Jack Eichel to the tune of 40 goals and 63 points in his first full campaign with Buffalo. They rewarded Skinner with a monster eight-year deal worth $72 million before splitting up him and Eichel, leading to 26 fewer goals for Skinner.

It's almost like the Sabres should have known who was driving the bus for the line, right?

They now have one of the most untradeable contracts in the league and possibly in league history. The contract was misguided in the first place and isn't going to look better as Eichel is done in Buffalo and Skinner is 29.

 

Calgary Flames: Milan Lucic

Year Signed: 2016

Seasons Remaining: Two

Cap Hit: $6 million

The Calgary Flames aren't responsible for the terms of Milan Lucic's contract. However, they willingly traded for him, so he is designated as the team's worst contract. As already discussed, all of these deals weren't made in a vacuum. There are circumstances at play for everyone in the NHL, and this case is no different.

Lucic isn't the runaway worst contract in Calgary, and few would argue that the Flames would be better off with James Neal in the lineup on a nightly basis. Those forwards were dealt for one another (with Lucic arriving with a conditional third-round pick). One could easily argue that Calgary did the best it could by turning a fading Neal into Lucic, who, at the very least, is zero fun to play against. 

He had a bit of a bounce-back campaign a year ago, putting up 10 goals and 23 points across 56 contests. Lucic still isn't worth his $6 million cap hit, but considering Neal is just barely hanging on at the NHL level, the Flames did just fine in this trade.

Still, on a roster full of tough choices to make on various players over the next few years, Lucic has the worst deal for Calgary. Stay tuned to see whether that remains the case a year from now.

 

Carolina Hurricanes: Brady Skjei

Year Signed: 2018

Seasons Remaining: Three

Cap Hit: $5.25 million

Teams in the NHL always seem to get hung up on pedigree. If you got selected in the first round within the past few seasons and don't have any off-ice issues associated with you, odds are good that a team looking for a bargain will think it can get something out of you that no one else has been able to.

When the Carolina Hurricanes traded for Brady Skjei in February 2020, it seemed like that is what they were trying to do. It's not like 6'3", 210-pound blueliners grow on trees, after all.

Skeji wasn't all that great for the Canes following the deal, though, and he took a pretty big step back in 2020-21. We'll say it over and over again: It's tough to judge any player for what they did or didn't do during that pandemic-affected season, but we can't simply throw it out, either.

At 27, could Skjei evolve into a player who is at least closer to being worth his $5.25 million cap charge? It's possible. Maybe he has an opportunity to shine now that Dougie Hamilton is no longer with the Hurricanes. The fact is that he hasn't panned out in Carolina just yet.

Until he finds his game or his contract expires, Skjei has the worst contract for a generally well-run organization.

 

Chicago Blackhawks: Seth Jones

Year Signed: 2021

Seasons Remaining: Eight, but the extension hasn't even kicked in yet!

Cap Hit: $9.5 million

Hey there, Chicago Blackhawks fans. Are you tired of hearing about how awful Seth Jones' contract is even though he only signed it at the end of July? Then the next nine years are going to be even worse, because this is a deal that isn't going to age well.

The massive extension Jones received before pulling on a Blackhawks sweater over his head raised eyebrows among some of the team's best beat reporters. And even if he plays like a $9.5 million defenseman in 2021-22, his new deal doesn't kick in until next year.

Yikes.

Half of Jones' contract will take place during his early 30s, and NHL players just don't typically improve as they creep toward 35.

There are exceptions, but organizations usually aren't betting $76 million that a player will prove to be a special case.

Chicago ignored the fact that Jones has been on a downward trajectory for three straight seasons. The Blackhawks ignored the fact that a bad Columbus Blue Jackets was better in terms of expected-goals-for percentage when their perceived No. 1 defenseman wasn't on the ice for them. The red flags surrounding this deal are numerous and real.

We hope Jones can live up to his megadeal. The odds just aren't in his or Chicago's favor.

 

Colorado Avalanche: Erik Johnson

Year Signed: 2015

Seasons Remaining: Two

Cap Hit: $6 million

The Colorado Avalanche have the cleanest cap sheet in the league. Darren McCarty and the rest of the '97 Detroit Red Wings would even take a glance at Colorado's salary situation, quietly nod in approval and move on with their days.

That is to say that even the biggest Avalanche detractor has to look at what they have built over the past several seasons and respect it. If the Tampa Bay Lightning are the latest threat to become an actual dynasty, Colorado's turn is coming.

Possibly as soon as this season.

As such, they don't have any glaringly awful deals that they have to contend with. Any player can fall off at any time for numerous reasons, but as far as what we can guess at, the Avalanche haven't exposed themselves to much risk because they have extended their core out for the foreseeable future.

So the "worst" contract designation goes to Erik Johnson, who just barely isn't worth his $6 million cap charge. Yeah, it's a great time to be a fan of the Avalanche.

 

Columbus Blue Jackets: Zach Werenski

Year Signed: 2021

Seasons Remaining: Six

Cap Hit: $9,583,333

From a public relations and club pride standpoint, we 110 percent understand why the Columbus Blue Jackets inked Zach Werenski to this contract. The club has done all it can to bring talent to Ohio, only to see players bolt for more attractive cities via free agency or forced trades.

Even the Jackets' own first-round draft picks have taken to forcing their way out of town before having much leverage to do so.

So when a player of Werenski's caliber and pedigree decides to call Columbus home for six years, well, it matters more to the organization from a "statement" standpoint than an on-ice one. Still, if we go after Chicago for making a statement for acquiring Jones, we have to hold the Blue Jackets similarly accountable.

Werenski is only 24, so he could well grow into this deal. This one definitely falls under the not hopeless heading. But this isn't a player who has established himself as an elite defenseman. And his cap hit will be higher than both Cale Makar's and Charlie McAvoy's once this extension kicks in. Who would you honestly rather have if you're a Blue Jackets fan?

This is a player who's never received a single first-place Norris Trophy vote making more than two defenders who finished last year second and fifth in voting, respectively. Can he live up to the nearly $10 million cap hit? 

Maybe. Until he does, though, this is Columbus' most questionable contract.

 

Dallas Stars: Tyler Seguin

Year Signed: 2018

Seasons Remaining: Six

Cap Hit: $9.85 million

This kind of $10-ish million cap hit is starting to become a trend as we break down the worst contracts across the NHL. Preferably, you would be in a position similar to Columbus or Colorado, where you have a skater who could grow into their cap hit or is coming off of the books relatively soon.

With Tyler Seguin, the Dallas Stars aren't in either comparably enviable position.

This is a forward coming off of an illness that limited him to three games in 2020-21. This is also a player who scored 30 fewer points in his most recent full season (2019-20) compared to the year prior (2018-19). That isn't the kind of track you want someone like Seguin to be taking.

Yet here we are, just three years into an eight-year contract that could end up being a pretty massive anchor on Dallas' books. Seguin is being paid like one of the NHL's elite forwards. He's expected to do a lot of things for the Stars, but as he enters his year-30 season, it's unlikely that he will find the nearly point-per-game pace he enjoyed in his mid-20s.

We don't make the rules. Nor do we control players' hour glasses or the effect Father Time has on their play. We just know what's happened in the past, and skaters in Seguin's position haven't generally gotten better as they have gotten closer to 35.