>But the big difference I see in this case is that many legitimate businesses work with crude oil so not all of those people are gambling / willing to gamble.
But those aren't going to be the losers. Oil producers typically sell their future contracts immediately to lock in a good price. Likewise, oil consumers are typically going to be buying oil futures early, hold them until they expire, and take delivery. In either case they're not going to be affected by the price going negative on the day of expiry.