I once read an argument (maybe here on HN, I'm not sure) that if insider trading were legal, Enron wouldn't have taken anybody by surprise. I'm not sure I buy the argument that it should consequently be legal, but it's an interesting idea.
It seems like the system mostly prevents massive Enron style fraud.
Sino-Forest has probably been the largest and most well known (as well as Valeant and their fake pharmacies) along with a bunch of Chinese small-medium-cap reverse IPO's like CCME
There was a Planet Money podcast about this [0] that if I remember correctly said it wasn't even explicitly illegal in the US until relatively recently. It was considered theft to take insider knowledge, but not illegal to trade on it.
[0] I think it's this one: https://www.npr.org/sections/money/2015/12/23/460689797/epis...