Yes, he could face jail time. Before someone is sentenced to jail time a hearing must occur and they must be found guilty of a crime.

Typically, if jail time was going to occur or it was an option it would have already occurred.Contact your local law enforcement agency to determine possible consequences for him as a result of his actions.

If a citation was issued with a future court date, he could be found guilty by a traffic judge and sentenced to jail at that time. Driving on a suspended license will cause some action to be taken by the court. This action can include getting your license suspension time lengthened or license revoked, fines or even jail time. This is a serious offense in most states.

Driving without insurance will probably require the driver to comply with the financial responsibility laws of the state and comply with those requirements. Typically, this is an SR22.