The sad reality of this situation goes beyond whether or not "to tell or not to tell" the company. Its really about character and integrity. A person who tries to "reduce" the severity of his actions (petty theft and habitual use/distribution) is not worthy of becoming a driver in the first place.
If a person is willing to steal and/or earn money through illegal actions, he is more likely to rob a package car blind down the road.
A person like this never developes "character", and merely stopping because of a drug conviction and a petty theft charge only delays the larger scope of the illness that created the need for these actions in the first place.
While I support his taking a legitimate job in the meantime, his deceptive persona only lends itself to suspicion.
A drug user/seller never stops taking drugs without a treatment program and detoxing. They may hold off for a bit until the "heat" cools down, but it always resurfaces.
At the end of the day, a person like this will enter the driving classification then ultimately get caught in a RANDOM DRUG TEST and it would be all over anyway.
Personally, this type of guy makes it tougher on everyone else, for when his background surfaces, it will force the company to take more "intrusive" actions when looking into perspective employees in the future.
I worry about the potential for theft from the daily dispatch he would be responsible for and alone to safeguard.
I have seen many cases where a driver with a drug and/or alcohol problem will trade packages for each on the route.
If it seems like I dont quite have the sympathy for this guy, then you would be correct as I see the "larger" complications of his personality.
If the company had random tests for part timers who are in the bullpen for driving, we would see a ton of disqualifications.
My recommendation for his guy is simple, First, get some treatment for your problem, pay your dues to society through your convictions, change your mindset, develope some character and integrity and work as if the stuff you are handling is the most important objects you will ever have in your hands.
If you truly have a felony conviction on your record, man up, take your medicine, pay the price and tell the company the truth. Part of punishment for a crime are the repercussions that come along with it. This will help you create character.
The extent of punishment for a crime goes beyond the courtroom, what happens to you after a conviction of a crime in this country is a part of the learning process.
If by coming forward and telling the company of your felony conviction costs you your job, then it should be viewed as a lesson learned and NOT an inconvenience.
Good luck,
Peace.