If the San Jose Sharks want to sign one of their young players to an eight-year extension, they're against a tight deadline, as the current CBA expires tomorrow and will be replaced on Wednesday.
While there are technically six players on the Sharks roster currently eligible for an extension, Barclay Goodrow, Adam Gaudette, Dmitry Orlov, and Luca Cagnoni are not likely in the mix to sign an extension with the maximum term. The only two players on the Sharks who could potentially sign that type of deal would be Will Smith and Yaroslav Askarov.
Smith seems like the most likely player who could sign an eight-year extension, but based on Mike Grier's recent track record of signings, the Sharks are looking to keep their core players signed for 3-5 years on their current cycle of contracts. If Smith really wanted to commit the next eight years to the Bay Area and took a lower average annual value to make it happen, I doubt Grier would argue, but that would be the only logical way for that to come together.
Askarov on the other hand is an interesting one. Goaltenders are notoriously hard to predict, both on a game-to-game basis and in regards to long-term development. If the Sharks signed Askarov to an eight-year deal, it would carry a substantial amount of risk, but it has the potential to also work out tremendously well in the long run if he reaches his potential. If not, it could tank everything that they've been building for.
In general, it seems like the Sharks are unlikely to sign a player to an eight-year contract before the upcoming deadline, which will reduce the longest term to seven years. With that being said, stranger things have happened in the hockey world, so it's impossible to rule out.
