Oilers are in cap trouble. They have about $10 million of space right now, but they couldn't / can't touch it because the money will be needed for the McDavid contract next year.
Right now they are projected to have about $13 million in cap space for next year, but they will have 10 players to sign to fill out their roster. Not good.
https://www.capfriendly.com/teams/oilers
Too many overpaid players on the roster are making things difficult. Lucic, Nugent-Hopkins and Russell would be the best examples.
My memory is not too good on this, but didn't Chiarelli have a full head of hair when he became the GM in Edmonton?