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Drug Enforcement Administration agents stopped Sokolow in Honolulu International Airport after his behavior indicated he may be a drug trafficker: he paid $2,100 in cash for airline tickets, he was not traveling under his own name, his original destination was Miami, he appeared nervous during the trip, and he checked none of his luggage. Agents arrested Sokolow and searched his luggage without a warrant. Later, at the DEA office, agents obtained warrants allowing more extensive searches and they discovered 1,063 grams of cocaine.

Did the search violate the Fourth Amendment?

The Court upheld the search and reasoned that the agents had a "reasonable suspicion that respondent was engaged in wrongdoing." Chief Justice Rehnquist argued that the validity of such a stop should be based on the "totality of the circumstances," (United States v. Cortez, 1981), which, in this case, gave agents a clear reason to suspect Sokolow of drug trafficking.