So there are 4 things that can happen this season.
1. Oilers miss playoffs
2. Oilers make playoffs as WC1 or WC2 and get bounced after a waste of 8 days
3. Oilers make playoffs and go on a run
4. Oilers win Cup
Now as we know 4 won't happen, that leaves 3 outcomes for this season. So what outcome leads to the worst misery for the Oilers next year and onwards? One of the following happens next year.
1. Draisatl signs a contract extension prior to 24/25 season
2. Draisatl is traded prior to the 24/25 season
3. Draisatl signs a contract extension during the 24/25 season
4. Draisatl is traded during the 24/25 season
5. Draisatl plays out the 24/25 season and walks as a UFA
Which outcome is the worstbfor them? Obviously walking to UFA when the team loses him for nothing. Which outcome is the worst for those that hate the Oilers? I'd say Draisatl traded prior to 24/25 season as they might luck into accidentally filling some gaps around Mcavi and icing a complete team for once, unintentionally.
So what outcome for this season produces the beat chance to allow for walking to UFA? Sadly, it does mean they make the playoffs this year, because missing would cause more drastic changes like possibly trading Drai, especially if he says he won't sign after a missed playoff season. So the team needs to feel like this was an off-year and the want to run it back one more time in this window.
TL/DR - For the most misery for the Oilers, I hope they make the playoffs this year and are promptly eliminated, so they think they can run it back one more year which gives the best chances for Draisatl to head to UFA and he walks for nothing, otherwise they might trade Drai prior to the season and luck into icing a more complete team.
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