**First of all, I have no inside information and this is purely speculation!!**
I just read over the requirements for the Disney Legend award and although it might be a little bit of a stretch, how would you feel if Matt Ouimet was awarded this at the D23 Expo for his work on Disneyland's 50th? The location would be perfect as its right across Katella from where he worked and it would be in front of the general public (who likely appreciate him more than any of the bigwigs in Burbank did).
Of course my pie in the sky dream would be for him to take the award and beat Jay Rasulo over the head with it, before announcing that he himself would take over as head of parks and resorts.