This is an excellent post.
I have observed that prior to the kid entering a particular school, the parents are clamoring for “One Strike and You’re Out” type of discipline. You do the “crime”, you do the time, whether it’s a one day suspension or something more seriously. Once their kid is at the school, it’s a 180 degree turnaround- parents report that their kid knows a friend is getting into serious stuff with substances, other problematic behaviors, and nobody will get the kid help because of “One strike and you’re out” and who wants a friend kicked out of school (or more typically, asked to leave in a genteel way).
Make sure your kid is on board with the school’s disciplinary policies before you make a decision. Humility helps. There but by the grace of god… etc.
So to answer your question- an honest, humble and transparent answer is the way to go. A school that is going to view your kid as a troublemaker based on what you’ve posted is likely not a fit– so better that they reject him rather than suspend him down the road. A school that will view his infractions in context is likely the better environment for him, no? So a brief but complete explanation would be my suggestion.