Any non-employee individual or business that you pay $600 or more to during the year must receive a 1099-MISC. (I think corporations are exempt.) You also need to get a W-9 from them, certifying that they're not subject to backup withholding.
So if you've paid him more than $600, you have to file a 1099-MISC. Tell him if he wants to work for $599/year, you won't have to file!