I remember being the same way. In 1st and 2nd grade I was a straight A student, working ahead in the books and just on top of everything. Then I transfered to a private school for 3rd grade and that is when everything got overwhelming.
I remember drawing a picture and getting yelled at for it because I was supposed to be doing an assignment and I didn't understand what the big deal was. I remember having a math test and not knowing how to do any of the problems at all and then just writing random numbers. None of it made sense to me but I got my test back and saw I failed and I remember just not caring because I didnt understand. Later on my mother told me she cried at night because I struggled so hard and was so frustrated.
I remember stealing around that time in my life too. I stole from 3 different stores in one day at one point..just stupid stuff like balloons or candy. I got caught because I offered some to my godmother after she took me with her to a party store.
She told my parents and they cracked down on me hard. I remember crying in my parents room. The made sure I understood that what I did was wrong. I remember after that I was different. But during that time in my life I wasn't able to comprehend certain things.
I'm glad my parents did what they did when they were strict with me. They made me go back to each store and return what I stole and apologize, it was hard but it opened my eyes. Now I am one of the most empathetic people I know but I'm not sure why I was like that back then. I always wondered why I was like that and then others around me seemed to be normal and not getting in trouble like me. I don't know how I didn't realize the things I did were wrong looking back on it but with the love of my parents I made it through.
No matter how angry I got, how much I failed, or anything I did, my parents never once gave up on me and they helped me grow to where I am today.
I think there method would work well here, enforcing punishment and maybe he should directly apologize to the principal himself. I also got in trouble when the secretary of my school used to give me my ADD medication everyday, i used to throw it on the floor after she walked away because I was mad that I needed it. They found out and my parents made me apologize to her.