The San Jose Sharks put on another impressive performance last night against the struggling Montreal Canadiens, beating them 4-1 for their fourth win in five games. That recent success has pushed San Jose into third in the Pacific Division, and right in the thick of the playoff race in the Western Conference. With that position though will come some tough decisions for the Sharks as we head towards the trade deadline, and teams around them start to load up for a postseason run. On one hand, the Sharks are in an enviable position. After Patrick Marleau walked in the offseason, and David Schlemko was taken from them in the expansion draft, the front office finds themselves with plenty of cap room to work with. In fact, CapFriendly projects the Sharks could add around $23.5MM of contracts at the trade deadline and still be cap-compliant. That’s an incredible asset when looking to take a swing at a Stanley Cup run, and could prove useful in the coming months. However, there is a larger problem that the Sharks must face when considering any deal. After adding the last few years, the team is without its second or third round picks in the 2018 draft, and don’t have a real glut of blue-chip prospects knocking down the door for an NHL job. More than that, their three key pieces up front are all unrestricted free agents either this summer or next, and starting next season they’ll have $15MM tied up in two defenders on the wrong side of 30. In fact, if you look at the team’s salary structure, draft stockpile, and prospect cupboard independent of their record this season, one might come to the conclusion that they need to consider selling instead of buying. They have several expiring (or near-expiring) assets that could still bring back impressive value, and might have a gap in young impact players coming through the system to replace them.