If you handled that properly it would work but it's tricky. Years ago, I took my oldest to a player signing. One of the New Orleans Saints. He was at the podium with his wife. He is African American, she white and blonde and maybe less than half his size. Obviously quite distinct from each other. My oldest was about 11 maybe closer to 10? I'm not totally sure. In any event, me being me I had him do something silly. I had him take his photo to be autographed and walk with it right to the wife and say to her loud enough for both of them to hear "Wow, you look much taller on TV Mr. ___". To my surprise, he pulled it off perfectly. There was a short pause. The wife got it and absolutely cracked up. The player looked at him for an extra few seconds and then his face lit up. He happily signed the photo and paused for a picture with my son. Could someone do the same thing with Jack? Maybe, but it would have to be well planned.