Jamie Benn

Friday was a very busy day for Jamie Benn.  First, he underwent surgery to repair an injured core muscle that leaves his availability for Team Canada at the World Cup in question.  Then the good news for him came in the form of an eight year, $76MM extension that makes him the highest paid player in team history.  It’s one of the richest deals in league history but falls just short of the top-10 of all time, at least in part.  Here’s a closer look at the priciest NHL deals ever.

1) Alex Ovechkin (13 years, $124MM) – Following his entry-level deal, Ovechkin essentially signed a two-pronged extension, one for six years at $9MM per season and then another at seven years and $10MM per year.  While you can’t call his contract a bargain, he has been one of the NHL’s top players for many years and is expected to continue to do so for a long time to come.

2) Shea Weber (14 years, $110MM) – Offer sheets have been few and far between in recent years but Weber was the most prominent to receive one as the Flyers inked him to a heavily frontloaded one in the summer of 2012.  Interestingly enough, offer sheets cannot contain any trade restrictions which likely played a role in Weber’s trade to the Canadiens last month.

3) Sidney Crosby (12 years, $104.4MM) – Prior to the current CBA which set a term limit of eight years on any contract, Crosby inked a highly frontloaded deal to stay with the Penguins until he’s 38.  The extra money up front was enough to keep Crosby at an $8.7MM cap hit, matching his sweater number.

4) Ilya Kovalchuk (15 years, $100MM) – New Jersey’s second attempt at a Kovalchuk deal in the summer in 2010 was enough to avoid another cap circumvention penalty.  That’s really the only good news that came from it as just three years later, Kovalchuk ‘retired’ to return to play in the KHL.  The Devils are dealing with a salary cap recapture penalty of $250K until 2024-25.

5) Alexei Yashin (10 years, $87.5MM) – This was an outright disaster for the Islanders, who inked Yashin to this deal back in 2001. He failed to come close to expectations and wound up being bought out with four years left on the deal at a cost of over $17.6MM.  On top of that, the Isles traded Zdeno Chara and the draft pick that yielded Jason Spezza as part of the package to land Yashin.

6) Vincent Lecavalier (11 years, $85MM) – Tampa Bay was hoping they had a fair deal with their franchise player at the time when they signed him to this deal back in 2009.  However, like Yashin, he struggled under the weight of the new deal while injuries took a toll as well.  The Lightning bought him out in 2013 and are in the midst of paying him over $32.6MM not to play for them through 2026-27.  Lecavalier retired earlier this offseason.

7/8) Patrick Kane and Jonathan Toews (8 years, $84MM) – Chicago inked their two superstars to identical contracts two years ago, a year before each were eligible for unrestricted free agency.  The Blackhawks continue to find ways to stay under the cap for now but that could become more of a challenge if the salary cap continues to stay close to where it is now as the years progress.

9) Anze Kopitar (8 years, $80MM) – Back in January, the Kings reached this deal with their new captain to avoid the risk of losing him to free agency this summer.  Kopitar has been Los Angeles’ most consistent forward for many years now and should remain their franchise forward for many years to come.

10) Jaromir Jagr (7 years, $77MM) – Washington signed Jagr back in 2001 to what was the richest deal in league history at that time.  However, the lockout in 2004-05 introduced a 24% rollback just two years into the contract which cost Jagr over $21.5MM in salary.  Jagr, now 44, is still going strong in the NHL and signed a one year, $4MM guaranteed deal with Florida in May.  He could also earn another $1.515M in games played and award bonuses.

If you take Jagr’s deal off because of the subsequent rollback, Benn’s new $76MM contract as well as Evgeni Malkin’s current identical pact with the Penguins become tenth on the all-time list.