I have different information about the development of Monkey Island 2:
Monkey Island was never a big hit. It sold well, but not nearly as well and anything Sierra released. I started working on Monkey Island II about a month after Monkey Island I went to manufacturing with no idea if the first game was going to do well or completely bomb. I think that was part of my strategy: start working on it before anyone could say “it’s not worth it, let’s go make Star Wars games” [Ron Gilbert, on his blog]
Anyway, I wanted just to add an opinion about the “it will never happen” mood that I have detected in some of the previous posts. I prefer to see it as probabilities. I would say that Disney selling the IP to Ron is extremely unlikely but not utterly impossible.
As long as Ron says things like…
Don’t expect me to ever answer this question… [If he had approached Disney and if they responded; LowLevel’s note] many people ask. It would not be in my negotiating best interest to say anything about any negotiations, or even if we’re having them. This isn’t to say we are, but I will never confirm or deny them." [Source]
… it means that he still thinks that it makes sense to protect his interests. These are not the words of someone who has thrown in the towel.
I don’t think about MI all the time but I think it’s fair to leave me an ounce of hope to see the trilogy completed, one day, maybe. 