Hi, Betsy! I will start by saying I get teary eyed every single time I watch the
Magic Kingdom Flag Retreat. As the wife of a disabled veteran, it's just so moving to witness this ceremony that acts as a daily thank you to veterans for their service and sacrifice.
The cast members at the
Magic Kingdom make the selection of a veteran to participate randomly each day. I have studied and questioned, and these are the best tips I can give you for increasing your chances that your son might be chosen.
First, they have to know you are in the military or a veteran. Wearing military themed clothing, like a hat or a t-shirt, might catch the eye of the cast members making the selection. Also, while I can't confirm what time this person is chosen, my suspicion is that it's pretty close to rope drop in the morning, so it can't hurt to get there early and talk to the cast members as you wait. I've had a couple of veterans tell me that they've talked about how much they appreciate all that Disney does for the military, and it seemed to help them get noticed and selected.
The one time my husband was chosen, I will say we all had our United States Navy t-shirts on, and he had just gotten his hair cut, so he was sporting his fresh high and tight. Anything that sets off your son - and your family - as proud members of the U.S. military might help.
Good luck, and thank you so very much for your son's service and your family's sacrifice.
Anna