It sounds like
A) He knows he’s doing something wrong
B) He not only does not care, he’s bragging that he’s getting away with it.
If he gets in a wreck, he’s stealing the other party’s time, money, health, and energy in dealing with the claims.
If he wants the privilege of driving, he needs to pay the associated fees and follow the rules just like everyone else.
He’s lying, cheating and stealing, and you know he’s lying, cheating, and stealing.
I advocate for reporting him.
However, your question is not “should I report him?” but : “am I morally obligated to report a crime I am aware of?”
There are degrees. It’s not like he’s stealing food from someone who won’t miss it, because his family with die without it (which is still stealing, but has more extenuating circumstances). He’s actually proud of / bragging that he’s taking advantage of the rest of the people who pay into the system.
Matthew 18:15-17: “If your brother sins (against you), go and tell him his fault between you and him alone. If he listens to you, you have won over your brother.
If he does not listen, take one or two others along with you, so that ‘every fact may be established on the testimony of two or three witnesses.’
If he refuses to listen to them, tell the church. If he refuses to listen even to the church, then treat him as you would a Gentile or a tax collector.”
He is putting others in financial danger every day by potentially causing an accident that someone else will have to pay for.
Catechism 1868-1869 states:
Sin is a personal act. Moreover, we have a responsibility for the sins committed by others when we cooperate in them:
- by participating directly and voluntarily in them;
- by ordering, advising, praising, or approving them;
- by not disclosing or not hindering them when we have an obligation to do so;
- by protecting evil-doers.
Thus sin makes men accomplices of one another and causes concupiscence, violence, and injustice to reign among them. Sins give rise to social situations and institutions that are contrary to the divine goodness. “Structures of sin” are the expression and effect of personal sins. They lead their victims to do evil in their turn. In an analogous sense, they constitute a "social sin."144
Would it put you in danger to report him? If not, I’m leaning toward yes. There is a moral obligation here to turn him in.
Best wishes in your difficult situation.
~E