He definitely sounds like an accident waiting to happen.

Not so much the fact that he did some questionable things, but the fact
that he brags about them.

Eventually he will hit some big sink while over the mountains, and
realize he doesn't have an escape route. Hopefully the sink will let
up before he crashes, and it will cause him to reevaluate his risk
taking practices.

Of course, it might just be occasion for him to brag again about what
he got away with.