Do I have an above average chance of winning a small claims court case in this set of circumstances?

An underaged driver operating a motor vehicle without a driver's license or insurance lost control (due to a failure to control speed - specified in the police report) and crashed through my property resulting in upwards of $2,500 worth of damage (between fence and pool repair in the backyard). Citations were issued for the licence and insurance part and witnesses place him as the driver. The vehicle was registered under his grandmother's name. It's unknown if he had permission to drive the vehicle (I would venture to say no, but his mother later arrived at the scene of the incident from my understanding).