Used to describe someone often involved in disruptive activities, may carry negative connotations implying disapproval. The manager called security when he noticed the hellraiser from the rival team enter the bar.
Pro Tip 2/3
Not Always Literal
Doesn't necessarily involve 'hell' or 'raising'; it's an expression for causing significant trouble or disturbance. Even though he never fought, his loud pranks made him quite the hellraiser.
Pro Tip 3/3
Informal Tone
It's informal and might be inappropriate in formal contexts like academic writing or professional emails. I wouldn't mention him being a hellraiser in the recommendation letter.