This article argues that, beginning with the 1909 Supreme Court decision in New York Central & Hudson River R.R. v. United States, federal courts have abandoned important principles that were intended to preserve civil liberties. By creating respondeat superior criminal liability, New York Central and subsequent decisions authorized a form of vicarious collective punishment that is inconsistent with these liberal principles. This change shifted the balance of power between prosecution and defense in a way that has had a pernicious effect on the methods employed by federal law enforcement agencies.