NHL teams slowly learning lessons about signing aging wingers

Rewind, if you dare, to the UFA forward class of 2016. Most teams who plunked down big bucks for the guys who hit the market at that time would rather forget. Paychecks aside, some of the players might, too.

Edmonton traded Milan Lucic this weekend after three unhappy years, and he might be the standard bearer for just how bad a bad contract can go. Especially if you’re making even worse decisions around it, as Peter Chiarelli did. (Maybe Brad Treliving didn’t get the memo in acquiring that deal, but that’s beside the point).

Joining Lucic were a number of other horrid contracts that were bad the day they were signed and somehow aged even worse. Lucic, at 28, signed a seven-year deal worth $42 million, most of which came in the form of bonuses.

Kyle Okposo, who’s a few months older, signed for the same term and that $6-million AAV, but somehow even more bonus money. Andrew Ladd being two years older than either of them cut his AAV by half a million, but not the term on that deal. Loui Eriksson sacrificed a year of term to get that half-million in AAV back.

With both being 32, Frans Nielsen and David Backes settled for less money ($5.25-million AAV over six years) or less term (five years at $6-million AAV) to really cash in.

Relative youngster Darren Helm got five years at an average of $3.85 million per, somehow from his old team, just in case you forgot about that deal. And finally, Troy Brouwer, 30, pulled in $18 million over four years.

Some other deals weren’t insane (Mikkel Boedker’s four years for $16 million, Matt Martin four years for $10 million) but they weren’t good, either. Many of the above deals also included no-move or no-trade protection of some kind, because why not?

For those scoring at home, though, every contract mentioned is one that came to be a source of regret for the teams, and many are still trying unsuccessfully to find a way out. Lucic and Martin got traded, the Flames bought out Brouwer.

More than half of these contracts outlasted the general managers who gave them away. Maybe that tells you something about how bad these deals are, were, and will continue to be. Don Sweeney, Doug Wilson, Jim Benning, and Brad Treliving — whose work keeps coming up in this for some weird reason — still have their jobs. Benning seems to be on thin ice as well, and Ken Holland is now running the Oilers, while Lou Lamoriello actively traded for the Martin contract after being ousted in Toronto.

The question is, though, whether the league’s GMs have learned from them. Treliving seems not to have, with the Neal contract getting signed last summer before inevitably going sideways (albeit probably a year or two before many expected), and now acquiring the Lucic contract to get out from under it.

The next summer saw regrettable contracts extended to Patrick Marleau (traded then bought out), Nick Bonino, Martin Hanzal, and Zach Hyman (all still lingering at or near the bottom of their teams’ depth charts), but none broke both the long-term and big-money thresholds seen in 2016. Which is certainly progress.

The Leafs traded Marleau to the Hurricanes, who then bought him out. (Stephen R. Sylvanie-USA TODAY Sports)
The Leafs traded Marleau to the Hurricanes, who then bought him out. (Stephen R. Sylvanie-USA TODAY Sports)

The next summer, some of those problems were back. There was the Neal contract, of course, but also too-big contracts extended to James van Riemsdyk, Ilya Kovalchuk, Jay Beagle, Antoine Roussel, and Leo Komarov. The Kovalchuk bet wasn’t a terrible one because it was relatively short-term and it hasn’t worked out at all for reasons beyond his own performance. Neal and van Riemsdyk were always likely to hit a wall, and van Riemsdyk hasn’t done that yet but he’s 30 and signed for another four seasons.

The other three guys represent what appears to be a different kind of market inefficiency, one that has carried over to this summer. A lot of the teams in 2016 made their big signings for guys who had (mostly) solid careers of putting up 40 or 50 points, as well as for being “leader” types who played 200-foot games. They paid a premium in both term and dollars to acquire it.

In the time since then, teams seem to be moving more toward specialization and, for the most part, the ask from players comes down — either in years or AAV, and definitely in terms of bonus dollars — as a result. No one would have said Neal or van Riemsdyk do anything for you but score goals, and they cost as much or less as a percentage of the cap than the 2016 class. As for the lower-end guys, they got more term and money than they deserve, but not six years and rarely more than $4 million against the cap.

That doesn’t mean there weren’t bad bets on forwards this summer. Mats Zuccarello’s deal with Minnesota is fine for now but, like van Riemsdyk’s, likely ages badly. And he still only got five years at 31, which can be considered an improvement. Brett Connolly got maybe a skosh over the right amount of money and too many years, but that contract is fine. Valtteri Filppula’s way overpaid and signed for two years, for some reason, but he doesn’t break Detroit’s bank. Brandon Tanev seems to be the outlier here, with an inexcusable contract in both years and dollars, but he’s only one guy, and unlike his predecessors he’s not hovering around his 30th birthday.

So it does seem teams are learning that maybe you shouldn’t give someone in their late 20s with a lot of hard miles on them big money for a long time. The recognition seems to be coming at a glacial pace — it’s the NHL, after all — and in some cases the bad actors here (Lamoriello, Treliving, Benning) are just making the same mistakes over and over.

But again, this improvement is only really seen among forwards. As far as defensemen go, well, it’s a different story entirely.

Ryan Lambert is a Yahoo! Sports hockey columnist. His email is here and his Twitter is here.

All stats/salary info via Natural Stat Trick, Evolving Hockey, Hockey Reference, CapFriendly and Corsica unless noted.

More NHL coverage from Yahoo Sports