What if he hired a driver to take him to work, instead?  Would that be a penalty?

What if he stopped at AA meetings on the way to or from work?  Pub 502 tells us,

You can also include in medical expenses amounts you pay for transportation to and from alcohol recovery support organization (for example, Alcoholics Anonymous) meetings in your community if the attendance is pursuant to competent medical advice that membership in the alcohol recovery support organization is necessary for the treatment of a disease involving the excessive use of alcohol.