Why was he dressed like a pirate?

he liked having his booty plundered

I took a creative nonfiction course with him at Ponoma back in '94. We weren't allowed to show anyone our essays outside of the class for some reason. He seemed naturally intelligent, didnt need to look at any notes or textbooks or prepare for any lectures, he just knew his stuff and was super casual.

I saw him talking to a girl on campus one day. He uncharacteristically wore a Fila sweatsuit, the kind that looks like it's made from the same material as parachutes, and trainer sneakers with a matching bandana. That was his pussy hunt outfit apparently. Several times a week, same outfit, I'd see him hitting on women in it. I once saw him wearing it while carrying an identical outfit from the dry cleaners, he had like 4 sets of same Fila sweatsuit.

I asked him about it in class and he said we aren't allowed to discuss anything unrelated to class while inside class, the same way we can't show anyone outside of class our essays. A student called out "but Dostoevsky isn't in this class and last week you talked about replicating his black tea obsession to test its affects on your own writing". Wallace stared blankly at the student with dead eyes for 30 seconds in dead silence then said "you just got knocked down a full letter grade. Any other smart asses? Didn't think so." and pushed up his glasses with his index finger.

I remember telling myself this guy will either be super successful or kill himself.