Prompt 1
Well this is easy enough, I'm going for the apparent idea behind this one and go with a Ciarelli trade. Not the Taylor Hall for Adam Larsson though, because although that one is quite bad I think there is another one that's worse from around the same time.
Edmonton trades 16 and 33 overall in 2015 draft to New York Islanders for Griffin Reinhart. Griffin went on to basically be only "potential" after he was already floundering cracking a not great NHL roster. Edmonton gave up 2 good picks in which is looked back on as one of the best draft years ever. The literal players who were picked with those picks are Matthew Barzel, and Mitchell Stephens (who?). Now if you want to say they might not have taken Barzel, then cool - Kyle Connor and Thomas Chabot were drafted right after. Gems like Aho and Hintz were taken around 33 as well. Imagine what could have been. At least Vegas took Reinhart away in the expansion draft.

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