Next time ask him how he feels/what he thinks about these sanctuary cites that will not enforce these unconstitutional mandates.
Then ask him if in his career he has come across something that just blew his mind that a particular person was capable of doing something horrific? And they say something like so if those things happened why is it hard to believe that there is ulterior motives to some of this.
You could also meet him from a place of leo and go down the hurtcore task force argo rabbit hole.