We were there during this promotion for Halloween, on Halloween day. (we went into the parks early in costume, even though we had party tickets for later). My daughter was dressed as Captain Jack (minus the facial hair), as she was obsessed with him at the time. We put a lot of time before the trip getting various accessories to make her look very authentic! Her long curly hair reached her rear at the time, so we just put a few tiny braids here and there with beads, too, it was SO great and pirate-y!
Anyway, back to the main topic, we were there early afternoon, she was in her full costume, and as we were coming off of the Pirates of the Caribbean ride, a cast member stopped her (she was age 8, my daughter, not the cast member, lol) and asked if she had met Captain Jack yet. She just stood there shaking her head no, she asked us if we'd like to come with her, and she marched us out to where the Pirate Tutorial was starting. She held her hand up, Captain Jack looked over, and she pointed down at my daughter. Captain Jack then asked her to be one of the kids for that performance.
It was spectacular, when it was her turn, he looked her up and down and said "this looks rather familiar!" Then he went to disarm her of her own weapons so that she could do her part, which was hilarious, as we had loaded her down with ALL kinds of fake swords, guns, knives, etc. She'd pull out another weapon and he'd say "do you have any MORE weapons?"
I was trying to take photo after photo with tears of happiness running down my face, lol. It was her first trip to Disney World, and to be there, with her "idol" was just beyond anything we could have ever imagined.
Later on that day, we were going across an area, and "Captain Jack" on his way to or from another performance saw her as he was walking and stopped for her.
Even now, if she's describing how good something was, she'll say "well, it wasn't a Captain Jack moment or anything"
So for us, it was the best promotion ever. It was everything I could have ever hoped for in terms of Disney "perfection". Heck, I still get tears in my eyes thinking of how great it was!
(On a side note, I mentioned her hair above...on that same trip at least 4 strangers reached out and touched my child's hair to ask if it was her "real" hair. That was so odd! Even Chip & Dale were tugging on it and messing around with it, lol. I told her they were thinking of lining their chipmunk home with it. She was fine with Chip & Dale, but not the humans!)
Edited to add: after that, we went everywhere trying to find that same cast member and finally did, and I got my daughter's photo with her and her "dream team" get up.