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Extra bonus points if you can invite him to the "events" and get the calendar to send him push notifications for occasional 5:30 am "wake up early for the thing". If he accuses you of bad faith for inviting him, tell him it's the default and you keep forgetting to remove him.
Not only will this annoy him, it will render the system impossible to supervise and you can always claim you ALWAYS organize your personals through your calendar and this "is just how i organize".
Good luck and give em hell.
Edit: Elaborated and more ideas
Edit 2: Few more ideas.
This was a fantastic read. OP I hope you do this (and then tell us about it or post screenshots)
Thank you. I consider myself a decent managerial saboteur / supervisional terrorist
Some people might take this further like spamming tech support/ IT with nonsensical tickets that somehow end up being something brought up to management which would force them to determine some policy (which they hate doing)
Others might find it amusing to open debates about how certain harmless terminology used in calendar events may cause offense to "people we should be looking after" due to "ideological considerations" "possibly triggering" even if no relevant members of any group are in the team. Some people may bring this up in HR.
The key concepts to destroy any organizational effort are "techincally allowed", "plausible deniability" and "could get someone in a lot of trouble".
IT here, please don't drag us into this... unless you're looking for help. We enjoy malicious compliance just as much as anyone else.