What are my options?

What is the name of your state? Michigan

I have a 15 year old boy who several weeks ago at a high school football game became angry with an individual and ended up taking a rock and "keying" the individuals car. There is no doubt that he did this, he admitted to it and also was caught on videotape at the school. Because this incident happened after school (although still on School property) the principle had some leeway in determining punishment. The school had decided to ban him from all extracurricular activities for the remainder of his sophomore year (and the year just started), he was also kicked off of his sports team as well. The person whose car this happened to had contacted the school and according to the principle did not want to press charges, he just wanted to resolve the issue. The principle told me that the person would be contacting me regarding payment of his deductible for repairs.

The Tuesday after the incident happened, my son had gone into school to see if we could get this persons name to contact them regarding taking care of this, they did not have his name available. About a week later, I get a call from the school athletic director requesting myself and my son to come in and meet with this person. This person now refuses to turn the claim into his insurance company because he said it will raise his rates (which I have since found out is incorrect because it would be covered under his comprehensive coverage) and wants me to pay a bill over $1,000. I have called around to 3 body shops for repair estimates and the highest estimate I received and this was for a worse case scenario was $800. I am afraid that if I do not pay this man the $1,000 he is asking for that he will then contact the police and press charges. What rights do I have? Can I request that he submit a claim to his insurance? Can I refuse to pay this amount and request three estimates for repair?

Well, the "guesstimates" you got are really just ballpark ideas - no reputable shop would be able to give you a firm number not having seen the damage. A $200 difference from a sight-unseen guesstimate isn't really that much. I'd ask to see the estimate(s) and then pay the dude. And then make my kid work his tail off to pay me back. At the end of the day - he caused the damage and it should be repaired.

I am aware that I will have to pay something and I am not disputing that. My son also knows that he will have to pay me back for whatever I do have to pay out. My problem is that I am a single parent with only 1 income and no child support. At most, I can give the man $300 today and then pay something else at the end of the month (I get paid monthly). My concern is that I feel that if I don't pay what he asks, then he will press charges against my son. I am trying to avoid involving the legal system as he is usually a good kid but made a very bad error in judgement. I don't want this to turn into something that can throw his whole life into a tailspin because I don't have a $1,000 laying around and can't borrow it from anyone.

Then ask the guy if you can arrange a payment schedule with him.

Write a letter to this individual explaining your situation, give it to the athletic director and ask him to see that he gets it. Leave it in his lap to decide what kind of a person he wants to be here...nice or a jerk. Most importantly tell him that you and your son know what he did was wrong and that you want to do the right thing. Also, I work for an insurance agent and there is a chance his insurance could go up but generally most companies have a 3 claims in 3 years policy. If he's had 2 previous COMP claims (not collision) in the past 2 years this COULD raise his rates. Ask him again if he wouldn't be willing to turn this into his insurance company and offer to pay the deductible or more to compensate him, again explaining your financial situation. You have no guarantee that he won't turn it into insurance anyway, have them pay for it, and take YOUR money as a lesson to your son.