The time you had to convince your GM about something. Bonus points if its reasons they should give you a magical item.

For me? It was the game itself... sort of. We were doing a Star Wars game post 6th movie and before we knew anything about the 7th movie on, and I wanted Thrawn to be in the game so badly I convinced the GM and the rest of the party to start a turf war with the new republic.

Place your bets!

Will he roll an absurdly high number through various bonuses he has, or will he Land on a Crit and get the sword that way?

I'm betting on being able to make a Reflex (for the sword dropping out of the air), Fort (for the sword touching his skin but not harming him), and Will save (for exerting his dominance over it) in order to overcome the curse, all boosted by situational boosts he gives himself like stances and the like to ensure he beats them all.

Does that not make any sense? Maybe, but it would be REALLY COOL.

Ego check.

The sword isn't necessarily cursed, its just really picky and "fails" to do what it needs to do at cruical times. So, Zoro convinces the sword he's going to crack open all kinds of whup-ass if it behaves, and if it doesn't he's leaving it in the bin.

Seems like a pretty easy choice.

My bet is that DM will let him have this so that he will be motivated to roleplay more.

There's a numerus dichotomy in the first speech bubble. Either "Every swordsman has come to a tragic fate" or "All swordsmen have come to tragic fates".

...or each swordsman has suffered multiple tragic fates and/or deaths.

A good curse screws you over. A great one screws you over nine ways to Sunday, in impossible ways.

It is a DnD game, someone casting revive on their party's tank only for the curse to hit again would be par the course.