Should I bring up a controversial extra curricular on my application?

How are you going to get into investment banking from Ole Miss? I’m rusty on what the exact target schools are, but I don’t think it’s one, maybe apart from boutique shops in Charleston or something.

Investment bankers value soft skills immensely, and they prize people who succeed progressively in conventional ways. Jumping the line on college might not be the best move if that is your goal. Now if it was tech you were after, that might be a different story.