When I worked for D. a couple of years back we had a written contract that he would hold back my pay to the tune of 500 dollars if I quit and did not return the van to his home location. We also agreed that he would take out 500 dollars for the deductible if I had a preventable accident. Having a contract is key, also you want to look for guys who have experience and references, as well as some back-up capitol. Even drivers need to be responsible with their money; that way they can remain profitable, and in turn generate revenue for their owners.
I spent 5 months straight on the road, available 100 percent of the time, repositioned on my own dime to better areas and scored loads, only turned down two mini runs in all that time, and my owner never appreciated it. Instead I was micro-managed and had 2500 dollars of my funds reversed out of my bank account because the guy put a stop payment on the check when I drove my truck 200 miles to Texas to the nearist Citibank location to obtain a replacement ATM card.
The owner was good, don't get me wrong. He paid on time, never shorted me, and he maintained the van well. He just didn't understand that Laredo, California, and out west were good places to find freight. He sat in Los Angeles once for a week and would never go back when I have had friends who get loaded out of Los Angeles 7 out of 7 times that they were there. It just goes to show, you need to have an experienced driver at the helm.
Any how, I wish you luck in recouperating the money for damages. But if you did not have a "written" contract that stated the owners responsibilities and the drivers responsibilties, you are going to have a hard time trying to go after the driver for monetary conpensation.