NHL insider Jason Gregor had an interesting perspective on why the Edmonton Oilers have so much pressure to win.The Oilers have lost in the Stanley Cup Final in back-to-back years, and Gregor believes the group is too serious. Gregor thinks that Edmonton needs to be more loose and fun, especially during the season."I'm actually going to go off the board here," Gregor said on 'The Sheet.' "I think the Oilers' organization right now is a very serious group. You can't win the cup in October, you can't win it in December. You can lose it by having a terrible run. They haven't done that. But I wonder just sometimes, if they ever really have any fun, right? They're such a serious group, and I think there's so much internal pressure to win now, because they've lost twice."Gregor believes the Oilers need to remember they are playing hockey and have fun early in the season."I would say the biggest issue for them is being able to exhale a little bit, and enjoy the process, rather than always, every decision you make, thinking that it's all about June," Gregor added.Part of the pressure for the Oilers is the fact that Connor McDavid has one year left on his deal, and he could leave in free agency.What did the Edmonton Oilers do in the offseason?The Edmonton Oilers have had a quiet offseason, with multiple players leaving the team in free agency.Edmonton traded away Evander Kane and Viktor Arvidsson, while Corey Perry, Jeff Skinner, John Klingberg, and Connor Brown all left in free agency.Edmonton did acquire top prospect Isaac Howard and signed him to an entry-level deal. The Oilers added Curtis Lazar and Andrew Mangiapane to bolster the offense and signed Evan Bouchard to an extension.The Oilers have $225,834 in cap space.