Here's a photo, a snapshot, taken sometime in 1962, showing my grandfather (in foreground) and President Kennedy (extending hand), in profile. As far as I know, this is the only photo that shows John P. McGrail with Kennedy after he became president. I know of at least one other photo with Kennedy, I will endeavor to bring that one to the site.
I believe that this picture was taken in Boston in 1962, but I cannot be certain of this. I have not identified the other people in the photo, but I will try to find out who they are.