As an Oilers fan I'd hope he wouldn't give up a ton of assets in a trade two weeks before the season starts for a guys rights, who A) you have no idea what his ask will be from the organization contract wise and B) has the worst agent in the league who's known for having his clients sit out when they don't get what they want.
And I'm sure Overhardt and Trouba's ask wouldn't be outrageous when they know how bad it would look on Chia to have a player he just gave up a **** ton for sit out.
Trouble is a hell of a player but between the timing, the fact he doesn't have a contract, who his agent is and the fact he's requested a trade I can't see the Oilers being interested unless the trade price was heavily discounted.
Trouba's contract demands are likely too big. I think Chia is fully prepared to give McDavid $10 million +. That's why he went and got the cheaper Larson over Subban