How to ruin life?

I have the mission of 'removing' a person who was annoying but I can't seem to complete the mission. I gave warrent for his arrest and deleted all college qualifications. I also changed his social status to deceased and changed his social security number.
What more must I do?
😕

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You were faking it? I was following you the whole time!

You must give this person at least 2 separate convictions and then enter 'parole' as a conviction. Once this is done, the arrest will be authorized! Fast forward a couple of hours and then check the news to see the headlines & collect your loot!

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Jump HIGH & Swing HARD!!