Who has the drive? If you have it, just tell him you're going to hold on to it until he's got cash for it.
If he has it, tell him you want cash... no more checks. If he has the money in a checking account, tell him to write a check to himself and go cash it.
Either way, tell him he owes you $15 more for the fees you were charged on account of his dumb ass.
Most importantly, you don't give a crap if he's well-liked or not. It doesn't change the fact that the dude clearly sucks with money and owes you $15 because of his piss poor money management skills. If he's pulling this crap, then I kind of doubt that this is a professional level job... and it really doesn't matter what people think of you in this type of job.