O Captain; (Stay) My Captain

As this season continues to plummet, the Islanders have started looking towards the future and whether that future includes John Tavares.  Tavares an ufa after next season is eligible to sign an extension this summer.  The panic has started setting in that he might leave without the Isles receiving any compensation.  Throughout history this has been a terrible play for the team that originally has the superstar.  As important as it is for teams to get a player like Tavares they don’t trade their top players, they want to add Tavares to the mix.  No matter how much Toronto wants Tavares, they will not be sending back a package that includes Auston Mathews, they would be lucky if the package included Mitch Marner.  This is why nearly all trades in this situation have the superstar in their prime being traded for multiple younger players who if everything worked out well would not equal the superstar.  It would be a safe to assume the Islanders would be giving up the clear best player in the trade.
This would be an organizational shifting deal.  Looking through fairly recent history the best comparisons are the Flames trading Doug Gilmour to Toronto and the Bruins trading Joe Thornton to San Jose.  Doug Gilmour was 28 years of age (Tavares will turn 27 in September) when he was traded from the Calgary Flames to the Toronto Maple Leafs.  Gilmour was near the end of a reasonable deal when he demanded a trade out of Calgary in hopes of getting a new contract.  During this time holdouts were prevalent throughout the NHL and Gilmour started his holdout in the middle of the season and was traded the next day.  This might be the most lopsided deal in NHL history.  It rejuvenated the Maple Leafs and was the beginning of the end for the Flames.  Yes, the Flames made many terrible deals after this but this was the first decision that lead to every other bad decision they made.  This deal was already being talked about due to Gilmour wanting to leave Calgary but the holdout only increased the speed of the deal.  This shows how little leverage the Isles will have if they decide to trade Tavares and how lackluster any package they get could be.  The biggest difference here is the Isles still will have the opportunity to offer Tavares the best contract and that chance is better than a possible return.
When the Bruins traded Thornton, he was 26 years old and they traded him in the middle of the season to the Sharks.  This was a traditional 3 for 1 deal in which the Sharks traded Wayne Primeau, Marco Strum, and Brad Stuart.  None of these players made any impact at all in Boston, while Thornton is still successful in San Jose.  There was really no reason for the Bruins to make this deal other than a terrible start to the 2005 season.  This still shows how difficult it is to trade a superstar even when the trading team has the leverage.  The Bruins were able to rebound after two seasons at the bottom of the east but none of the guys they received for Thronton had any impact on them getting there.
There are truly only a handful of great forwards that were traded at this point in their careers.  In addition to Gilmour and Thornton, the trading of Gretzky, Jagr, Ron Francis, and Dave Andreychuk were varying degrees of disasters for their organizations.  The only trades that could be considered acceptable were Dale Hawerchuck going from Winnipeg to Buffalo for Phil Housley and Mike Gartner going from Washington to Minnesota for Dino Ciccarelli.  With positive deals coming few and far between, trusting Garth Snow to buck this trend would be a mistake especially since the odds will already not be in the Islanders favor.
The final example to look at is Steven Stamkos.  This is the path the Isles need to take in in this situation.  Stamkos was a ufa last summer and tested the market before resigning with the Lightning.  If Tavares does not sign an extension over the summer keep the lines of communication open.  Use him to help rebound this team next season, and give the Isles the best chance they can at contending next season. As Stamkos saw over the summer the best opportunity may not be somewhere else.  Once the Islanders trade Tavares, they have given up all hope of bringing him back, if they don’t there is always hope he will resign.  History has shown that the package the Isles will receive for him will not be enough to make the risk too much.  It is better to take the risk to keep him long term than it is to just accept 40 cents on the dollar and get out of the way.