Jeff Carter, Mike Richards

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.

What will Brent Burns’ new contract look like?

SAN JOSE, CA - FEBRUARY 29:  Brent Burns #88 of the San Jose Sharks celebrates after scoring a goal in the second period against the Montreal Canadiens at SAP Center on February 29, 2016 in San Jose, California.  (Photo by Ezra Shaw/Getty Images)
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There’s only one Brent Burns, that much is clear. Both on and off the ice, there’s no one like him.

So, what do you pay a guy that’s always imitated, never duplicated?

That’s the dilemma the San Jose Sharks will be faced with in the coming weeks/months.

If you were impressed with Bruns’ 17 goals and 60 points in 2014-15, then his 27 goals and 75 points in 2015-16 was out of this world.

Over the last three seasons, not many forwards have produced as much as Burns, let alone defensemen.

Since being acquired by San Jose in 2011, Burns has hit double digit goals in all but one year (he scored nine in 30 games in 2012-13).

“You know how we feel about Brent. Phenomenal year,” GM Doug Wilson said back in June. “When we acquired him it was a big piece to acquire. There’s no doubt he’s important to us. We want him. I think he loves being here. Those conversations will take place shortly.”

Time to talk numbers…

It sounds like Burns enjoy playing in San Jose, so him taking a bit of a discount is possible. But if we look at the closest comparable…

Dustin Byfuglien, who is 31-years-old like Burns, signed a five-year $38 million contract with the Jets this winter. That comes out to an AAV of $7.6 million.

Both are big, physically imposing and have put up some great numbers in the last few years.

Over the last three seasons, Byfuglien has scored 19, 18 and 20 goals for a total of 57. Burns has scored 27, 17 and 22 for a total of 66.

That’s not a huge difference over three years, but Byfuglien wasn’t coming off a 27-goal season and a trip to the Stanley Cup Final when he signed his contract.

Although we haven’t really heard much regarding Burns’ contract demands, it wouldn’t be shocking for the final cap number to be in the 8 or 9 million range.

Poll: Will the Sharks make it back to the Stanley Cup Final?

SAN JOSE, CA - MAY 25:  Deputy Commissioner Bill Daly presents the Clarence S. Campbell Bowl to Joe Pavelski #8 and the San Jose Sharks after their 5-2 win over the St. Louis Blues in Game Six of the Western Conference Final during the 2016 NHL Stanley Cup Playoffs at SAP Center on May 25, 2016 in San Jose, California.  (Photo by Thearon W. Henderson/Getty Images)
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Not many people expected San Jose to be in the Stanley Cup Final in 2015-16, but with expectations at an all-time low, they did it.

San Jose has put together some talented teams and before last season, they weren’t able to get over the hump. But now that they’ve gotten over the hump, expectations are back up.

How realistic are these expectations though?

On paper, the Sharks are still loaded. They didn’t lose much this off-season and managed to add speedster Mikkel Boedker in free agency.

Still, when you’re dealing with a number of veterans, you never know when their production will start to dip.

Joe Thornton, Patrick Marleau, Brent Burns and Joe Pavelski are all over 30. Marleau and Thornton are 36 and 37-years-old and they’re entering the final year of their contracts.

The Stanley Cup hangover is real. Although the Sharks didn’t win it, those veterans went four rounds and played in some grueling games along the way. Will they be in tip-top shape come October?

On a more positive note, those veterans are surrounded by some good young players. Logan Couture has developed into a go-to guy, Tomas Hertl proved to be a difference maker at times last year, Joonas Donskoi scored some big goals in the playoffs and prospects like Mirco Mueller, Nikolay Goldobin and Timo Meier are on their way.

The team also has some remarkable depth on defense, as Burns is joined by Marc-Edouard Vlasic, Paul Martin, Justin Braun and a few other key contributors.

Between the pipes, Martin Jones‘ first season as a starting goaltender went pretty well.

“A special group,” San Jose coach Peter DeBoer said after losing in the Stanley Cup Final, per the team’s website . “But only one team can win. That doesn’t take anything away from what those guys accomplished. I don’t think anyone should ever question the leadership or the character or the will of the group of men in there. I think it’s been misplaced for a decade.

“I would hope they answered some questions. Let’s be honest. Not many people had us making the playoffs. Not many people had us beating [the Los Angeles Kings in the first round]. On an on. I thought a lot of questions were answered by that group.”

It won’t be easy for them to make it back to the final. They’ll have some stiff competition in Los Angeles, Anaheim, Dallas, Chicago, St. Louis, Nashville and any other team that might surprise.

So, can this “special group” do it all over again next season?

Time to vote!

Under Pressure: Patrick Marleau

GLENDALE, AZ - APRIL 04:  Patrick Marleau #12 of the San Jose Sharks during the NHL game against the Arizona Coyotes at Gila River Arena on April 4, 2015 in Glendale, Arizona. The Coyotes defeated the Sharks 5-3.  (Photo by Christian Petersen/Getty Images)
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This is part of Sharks day at PHT…

Before the 2016 playoffs, there had been a lot of disappointment in San Jose and Patrick Marleau has been there for all of it.

Over the last 18 seasons, Marleau has been the most productive Shark during the regular season. Unfortunately, he’s also one of the players that’s received the most criticism during San Jose’s playoff failures.

Last season, the 36-year-old saw his point total dip for the third straight year. Marleau was still productive (25 goals and 48 points in 82 games), just not as productive as he had been in previous seasons.

It’s no secret that Marleau’s been the talk of trade rumors for years. Even at the beginning of last season, it was reported that he submitted a list of three teams he was willing to be traded to.

“I’ve been here forever and it’s been a great place to play,” Marleau said last November, per CSN Bay Area. “I’m not going to get into specifics or anything like that. There’s always been rumors in my career. I don’t really want to feed into it anymore or comment on it. I don’t want it to become a distraction or anything.”

The Sharks held on to Marleau, and even though the rumors have died down, his days might still be numbered in San Jose (for real this time).

Marleau will be an unrestricted free agent at the end of the season and although he’ll probably make less than his current $6.66 million AAV, it could be the end of the line between these two sides.

The Sharks have younger players like Tomas Hertl, Mikkel Boedker and a number of prospects like Nikolay Goldobin, who will be ready to jump into the lineup soon.

With an aging core, Marleau might be the first veteran San Jose cuts ties with because Joe Thornton and Joe Pavelski are still performing at a high level.

Also, the fact that Thornton and Brent Burns both need new contracts after next season certainly doesn’t help Marleau’s case. And in two years from now, Tomas Hertl will be looking for a bump in pay as well.

The odds seem to be stacked against Marleau. If he wants to remain a Shark, he’ll have to take a significant pay cut or have a huge bounce back season.

Looking to make the leap: Nikolay Goldobin

SAN JOSE, CA - NOVEMBER 05:  Nikolay Goldobin #82 of the San Jose Sharks in action against the Florida Panthers at SAP Center on November 5, 2015 in San Jose, California.  (Photo by Ezra Shaw/Getty Images)
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Earning a roster spot on a veteran team that just went to the Stanley Cup Final won’t be easy, but Nikolay Goldobin will give it a shot.

The 20-year-old was drafted in the first round, 27th overall, in 2014. He has speed and skill and could be ready to make an impact at the NHL level as soon as this season.

Goldobin got his firs taste of NHL action last season, as he scored a goal and an assist in nine regular season games with the Sharks between Oct. 16 and Nov. 22.

Although his agent Igor Larionov admitted that his client wasn’t ready for the NHL last season, it’s a different story this time around.

Goldobin now has a full year of pro hockey under his belt and he his time in the AHL certainly helped too.

Here’s an excerpt from a recent CSN Bay Area article about Goldobin:

Headed into camp, Goldobin may be penciled in to start the season with the Barracudas, but I would imagine he’ll be given every opportunity to shine in some preseason games. As a skilled winger he’ll need to be on a line with a top center, so perhaps he gets a look with Joe Thornton or Logan Couture. There is always the chance Goldobin could push someone like Tomas Hertl, Melker Karlsson or Matt Nieto down the lineup, or maybe even a veteran like Patrick Marleau. It may not happen right away, but if Goldobin starts the year in the AHL and is tearing it up, he won’t have to take a cross-country flight on a recall. That should make some current Sharks a bit nervous.

In his young career, Goldobin has already a little success playing with Thornton:

The Sharks currently have 13 forwards on the roster, but that includes the two-way contracts of Joonas Donskoi, Chris Tierney and Micheal Haley.

Although Donskoi’s job appears to be safe, the other two players could become victims of Golbodin’s training camp success.

With everyone healthy, the Sharks likely won’t have a top-six roster spot Goldobin, but potential injuries could fix that problem too.