Are ultra long-term contracts a blessing or curse for the teams that issue them?

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Since the salary cap era started, teams have been becoming more and more open to signing players to extremely long-term (basically lifetime) contracts in an effort to provide themselves with cost certainty. It also allows them to give players the type of money they want now, while keeping the overall cap hit low by frontloading the deal. In turn, players get the security that a long-term deal provides.

It seems like a win-win scenario, but of course it’s not that simple.

The NHL owner’s initial CBA proposal sought to limit contracts to five-years in length, but even if these types of ultra long-term deals are still an option next season, should GMs be interested in signing players to them?

To get a better idea of the potential pros and cons, let’s take a look at the five longest active deals that have been in effect for at least three full seasons.

Rick DiPietro (New York Islanders – 15 years, $67,500,000) — Obviously, this deal perfectly sums up the risks involved. The deal began in the 2006-07 campaign and at this point a $4.5 million cap hit is pretty low for an all-star caliber goaltender.

The problem, of course, is that DiPietro is not an all-star caliber goaltender. He’s been plagued by injuries over the last four seasons and hasn’t even been that good during the brief periods where he’s been healthy.

At this point, he’s the Islanders backup goaltender and someone who probably wouldn’t be able to find a one-way contract as an unrestricted free agent. All the same, the Islanders have made a commitment to him that lasts through the 2020-21 campaign.

Alex Ovechkin (Washington Capitals – 13 years, $124,000,000) — Going into this deal, Ovechkin looked like about as safe a bet as you could get. Sure, his $9,538,462 cap hit was excessive for the time and is still the biggest in the NHL, but could you blame Washington for locking up a man that promised to be one of the greatest goal scorers of his generation?

To an extent, yes. It doesn’t matter who the player is, assuming that he’ll be among the league’s elite for the next 13 years is a big gamble. It hasn’t exactly blown up in Washington’s face, but Ovechkin’s 38-goal, 65-point 2011-12 campaign certainly leaves something to be desired given his contract. Still, Ovechkin is young and over the span of his career, last season might prove to be the low point.

Henrik Zetterberg (Detroit Red Wings – 12 years, $73,000,000) — Zetterberg’s deal has fared better than most. His $6,083,333 cap hit is looking increasingly favorable given how much the market have risen in recent years. His offensive output did decline a bit in 2011-12, but he remained the team’s point scoring leader.

Mike Richards (Philadelphia Flyers/Los Angeles Kings – 12 years, $69,000,000) — This one is a bit harder to judge. The Philadelphia Flyers eventually decided to go in a different direction, but, in part due to his reasonable $5,750,000 annual cap hit, they were able to trade away his contract for a pretty nice haul.

He then went on to record just 44 points in 74 games in his first season with the Los Angeles Kings, but he stepped up in the playoffs and helped them win the Stanley Cup. His deal certainly can’t be called a failure, but it remains to be seen if he’ll be able to build off of his strong playoff run and have a more productive all-around season in 2012-13.

Marian Hossa (Chicago Blackhawks – 12 years, $63,300,000) — For the most part, this contract has worked out fine so far. Hossa helped the Blackhawks win the Stanley Cup and it’s hard to argue with that. His $5,275,000 cap hit is also pretty friendly and has made the deal justifiable even though he’s missed a decent amount of playing time due to injuries.

With Hossa, even after three seasons under the deal, the jury is still out. He’s already 33 and he’s signed through 2020-21. It might not be too long before his contract starts to look like a drag on the team.

In a way, Hossa’s deal encompasses the risks that we still can’t fully explore. Seeing as these types of deals gained popularity with the new (soon to be old) CBA, we haven’t gotten to see these deals play out through to their conclusion. However, we can already clearly see examples of the big risks these contracts come with.