"...half the tips??" That sucks.
Is minimum wage in Massachusetts $5/hour? Or is his boss being a jerk and claiming a tip credit against his wages? And making him buy his own gas on minimum wage (or less)? I work in a pizza place and I think all of our drivers would quit on that kind of system.
The owner's philosophy to employment is "My business is not a democracy." Although this is a slight exaggeration, there are certainly jobs that are reminiscent of this kind of BS. I remember working in a large chain men's clothing store and the official uniform was their clothes that I had to buy.