From any point in history, a spin-off of whether you would ask Hitler something or sock him in the face. Assume whoever you choose will answer truthfully and to the best of their ability, as if replying to a very close confidant. We’re also in an alternate universe where Eric Stoltz was never recast in Back to the Future - Great Scott! - so don’t worry about history.
If you have the know-how feel free to answer as you think they would.
I’ve got a list…
To Joseph Stalin - If the Germans hadn’t betrayed you in 1941, when would you have betrayed them?
To John Brown - Are you that badass because of your beard, or is your beard that badass because of you?
To George Washington - Does your Iroquois nickname of ‘Conotocaurious’ - town burner - bother you?
To James Madison - Is there any circumstances where you can imagine the Union of States fracturing and declaring war on each other?
To Charles de Gaulle - Has it occurred to you that it’s not all about you?
To Michaelangelo - Did you hide the human brain in the Creation of Adam?