Look back at the Duchene situation. While Duchene had more term (and thus more value) it’s similar to EK in that the Sens have a very high ask that teams aren’t willing to pay at this time. Sakic held onto Duchene for more than a year through the offseason in 2017 and into the regular season, long after Duchene was supposed to be gone.
Will it be uncomfortable? Probably, but that team is a ****ing train wreck that needs a major overhaul anyway, so who cares. If Dorion doesn’t get his price now, he holds onto EK into the season. Say McDonagh or Stralman went down in TC, or a Dman from a contending team that wasn’t even a suitor before? If someone doesn’t give you what you want in October, you deal him at the deadline. You may get a little less, but you will have more teams interested and you don’t care if EK wins you games this year because you don’t own your 1st and can’t tank anyway.
Edit: AM posted his Sakic reference while I was typing this.