I've laughed ever since United States v. Jones (2012), the GPS tracker-stuck-to-vehicle case.
The justices actively debated what the historical equivalent of 24/7 digital tracking would look like in 1791. This prompted the famous hypothetical of an officer secretly squeezing into the trunk of a horse-drawn carriage to track someone's movements over several days.
The issue here is that there's no practical way to ever update the Bill of Rights in the 21st century. Bug or feature?
The justices actively debated what the historical equivalent of 24/7 digital tracking would look like in 1791. This prompted the famous hypothetical of an officer secretly squeezing into the trunk of a horse-drawn carriage to track someone's movements over several days.
The issue here is that there's no practical way to ever update the Bill of Rights in the 21st century. Bug or feature?