They are the sort of contracts that drive Brian Burke and some of his fellow GMs crazy.
But right now, they're working for their teams.
New Jersey Devils star Ilya Kovalchuk's deal continues to stand as likely the wackiest in the league, as at 15 years and $100-million, it drew the ire of the league ( and Burke) when it was signed in the summer of 2010.
(The NHL ultimately penalized the Devils for attempting to circumvent the salary cap after it was signed, fining them $3-million, a third-round pick in 2011 and a first-round pick within the next four seasons.)
A year later, Brad Richards was the big free agent available, and he landed a nine-year deal for $60-million from the New York Rangers that includes a league high $12-million this season and next.
Both are huge contracts. And both come with low salaried final years and significant risk attached to their later seasons.
This season, however, they've helped put their teams over the top.
The Devils and Rangers are one win away from making the final four for the first time in a long time. New Jersey's last trip that deep in the playoffs ended with a Stanley Cup in 2003; New York was last there in 1997 when Wayne Gretzky was in its lineup.
Those droughts were what, in part, led them to take big risks on Kovalchuk and Richards, who entering Tuesday's games were tied for fourth in postseason scoring with 10 points.
Despite being hampered by a back injury and missing the first game of their second round series, Kovalchuk leads the Devils in scoring and is averaging nearly 25 minutes a game.
Richards, meanwhile, scored the tying goal on Monday night as the Rangers won a pivotal Game 5 at home, and has been a key part of their rise in the standings to the top of the East.
They're behind only Claude Giroux, Danny Briere and Dustin Brown in scoring with Round 2 winding down and both may yet emerge as Conn Smythe candidates in the next round.
It's worth noting the cap savings these two teams are getting on their stars, too.
The Washington Capitals, for example, have the highest payroll in the league and currently have Alex Ovechkin with the largest cap hit at $9.538-million a season for the next nine seasons.
Pittsburgh Penguins stars Sidney Crosby and Evgeni Malkin are next on the list with $8.7-million cap hits, with others who have made an impact in the playoffs like Marian Gaborik and Shea Weber carrying a $7.5-million hit this season.
Kovalchuk and Richards, meanwhile, both have cap hits of $6.67-million (28th overall) despite the fact they will make $8.5-million or more in at least five of the years in their deals.
Is that an unfair advantage? A little bit – and one only teams willing to spend up to the cap every year are willing to take on.
You won't see Nashville or Phoenix signs a gruesomely front-loaded contract like these.
This phenomenon of long contracts with meaningless years tacked on is all but certain to be written out of the next CBA, which leaves only one more summer of contracts (with Zach Parise and Ryan Suter up as UFAs) that be along these lines.
Given the success of Kovalchuk and Richards in these playoffs, perhaps more teams should bite the bullet and follow suit?