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Society has long struggled with the meaning of privacy in a modern world. This struggle is not new. With the advent of modern technology and information sharing, however, the challenges have become more complex. Socially, Americans seek to both protect their private lives, and also to utilize technology to connect with the world. Commercially, industries seek to obtain information from individuals, often without their consent, and sell it to the highest bidder. As technology has advanced, the ability of other individuals, institutions, and governments to encroach upon this privacy has strengthened. Nowhere is this tension between individual privacy rights and government security interests felt more acutely than within the context of the Fourth Amendment.

Notwithstanding the long duration of this struggle, jurisprudentially, the nation is at a critical point. Traditionally, the touchstone for analyzing the boundaries of Fourth Amendment searches is reasonableness. Quite literally, therefore, the Supreme Court has the task of determining the unanswerable: What is reasonable? This task, combined with the modern realities of rapidly changing technology, increased use of government surveillance, and changing expectations and conceptions of privacy, as well as differing perspectives of privacy in a heterogeneous society, becomes an even further complicated endeavor.

One of the significant realities in play at this critical juncture lies within the Court itself. This Article asserts that there is a new, different form of the digital divide — the divide between the perspective of the Court and twenty-first century realities — which negatively impacts Fourth Amendment jurisprudence. This Article focuses on two specific aspects of that gap, arguing that this gap in experience and perspective contributes to false presumptions by the Court, which then leads to less than optimal opinions. Such an approach creates a veritable house of cards in which the opinions themselves are weakened and erode over time. The potential of the Court to add crucial guidance in the area of privacy law in contemporary society is immense. That being said, any constructive impact is compromised when the validity of the opinions precludes their ability to withstand the test of time.

This Article discusses the gap generally, with specific attention paid to the divide between the Court and technological realities, and the gap between the Court and the realities of modern policing and pressures on law enforcement. The author argues that these divides result in opinions purporting to determine what is reasonable in modern life, but which rest upon a set of inaccurate presumptions. By analyzing Riley v. California, in which the Court held that the police may not dispense with the warrant requirement to search arrestees’ cell phones incident to arrest, this paper demonstrates examples of this gap. In particular, the article explores three inaccurate presumptions made in Riley, arguing that they contribute to a failed jurisprudence in this critical area. The article concludes by offering concrete steps to close the digital divide and allow the Court to more effectively influence this critical area of the law and modern life.



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