In the case of United States v. Hosep Krikor Bajakajian (1997), the U.S. Supreme Court ruled that confiscation by the government of money not reported to customs officials, as required by law, was a violation of the Eighth Amendment's Excessive Fines Clause if it was grossly disproportionate to the gravity of a defendant's offense. The court held this in favor of Hosep Krikor Bajakajian who had failed to report $357,144 while leaving for Cyprus from Los Angeles International Airport and consequently faced forfeiture under federal statute 18 USC Section 982(a)(1). This decision marked an important interpretation regarding proportionality in punitive fines and forfeitures imposed by state authorities.

In the dissenting opinion for United States v. Hosep Krikor Bajakajian, Justice Kennedy argued that the majority's decision to limit the government's power to confiscate property used in crimes was misguided and could potentially undermine law enforcement efforts. He contended that there is a long-standing tradition of allowing such forfeitures as punishment for criminal activity and this should not be limited by an excessive fines clause unless it is grossly disproportional to the gravity of offense. In his view, Bajakajian’s failure to report taking more than $10,000 out of country was part of a larger scheme involving illegal activities which justified full forfeiture under existing laws. The ruling by majority would make it difficult for courts in future cases because they will have difficulty determining what constitutes "gross disproportionality". Furthermore, he believed that Congress has broad authority over monetary regulations and their judgment on penalties should be respected.