My vengeance plan:

Step 1: Buy him a beer (or a soda or whatever)

Step 2: Don't just forgive him -- find a way to THANK him for crashing your car (make it up, it doesn't matter)

Step 3: If he ever brings it up again, act as if you can't even remember what he's talking about.

Repeat these steps for all similar offenses.

In 3-5 years you will have enabled his terrible subterfuge on several occasions and reinforced hundreds of terrible habits that will cripple him emotionally and professionally for decades to come. It'll screw with his relationships and ruin his perceptions of normal people, by making it seem like stealing and crashing someone's car is no big deal as long as they're cool like Awson. It's the perfect long con.