As a personal injury attorney who goes after people like you my suggestions are as follows. Get a printout of his driving record and make sure he is a safe driver. Hire him as an independent contractor not an employee. Make sure he has insurance and an ample amount. Make sure he doesn't use your vehicle or his vehicle with your signage on it too. In other words take prudent steps to make sure he and is vehicle are not a menace to society before you hire him and occasionally check up on him. Do this and even the best personal injury attorney will have a hard time trying to make out a case against you.

Good luck, and best wishes for a happy new year.

I agree with Mr. Belli. Additionally, keep in mind that just calling him or "hiring" him as an independent contractor may not protect you or your business. No matter what you call him the legal system (and IRS) make their own determination if the person is an employee or independent contractor (taking into account the work he's doing, how much supervision you provide, and other factors). I would highly recommend seeking the advice of an attorney to discuss these matters and having a good independent contractor agreement drawn up. Please let me know if I can help in any way.

Also, it wouldn't be a bad idea to contact your insurance broker to discuss insurance to protect you in case of an accident, etc.

I agree with the previous answers, especially the suggestion to ask your own insurance agent or broker if you are adequately protected by the deliveryman's policy and your own policies, taken together. Further, you should ask yourself why you want to make deliveries this way, when there are any number of true independent, licensed, PUC-permitted, etc. delivery companies, starting with U.P.S. and FedEx and working down to a guy with a truck. Start with someone on the "big" end of the chain; that usually equates to "responsible" and "well insured".