The personalized nature of conversations with chatbots, creating an atmosphere of privacy that encourages frank disclosure, can make logs held by AI companies richer than more conventional digital evidence such as search logs, according to legal experts. ‘It’s not just the question, it’s the whole prompt and the background you provided and the back and forth. There’s no guessing at what your thought process is and what you intended, it’s very plain,’ said Michael Price, the litigation director for the Fourth Amendment Center at the National Association of Criminal Defense Lawyers. ‘If ever there was a window into the soul to reveal the privacies of life, this seems like a good one,’ he said.
Data released by OpenAI shows requests by government agencies and law enforcement for user data growing rapidly. In the second half of 2025, the company disclosed data from more than 80 accounts, an increase of more than four times as many over the same period the year before. But when chatbot conversations show up in criminal cases, it’s often because the person involved in the chats allowed law enforcement to access them, Price said. When police ask someone to open their phone during questioning or after an arrest, they often do so, allowing officers to scroll through the apps they use, he said. In general, the Fourth Amendment, which protects people against unreasonable searches and seizures of their property, provides the right to refuse a search of the contents of their phone unless police have a warrant. ‘The short answer is that most people consent,’ Price said. They shouldn’t, but they do.’
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"If it was easy, everybody would be doing it. It isn't, and they don't." —Me
"Life is not a matter of holding good cards, but of playing a poor hand well." –Josh Billings (pseudonym of Henry Wheeler Shaw), Josh Billings on Ice, and Other Things (1868) (erroneously attributed to Robert Louis Stevenson, among others)
“I am still learning.” —Domenico Giuntalodi (but misattributed to Michelangelo Buonarroti (common phrase throughout 1500's)).
"Love work; hate mastery over others; and avoid intimacy with the government."
—Shemaya, in the Thalmud
"It is a pleasant world we live in, sir, a very pleasant world. There are bad people in it, Mr. Richard, but if there were no bad people, there would be no good lawyers."
—Charles Dickens, “The Old Curiosity Shop ... With a Frontispiece. From a Painting by Geo. Cattermole, Etc.” 255 (1848)
"A system of law that not only makes certain conduct criminal, but also lays down rules for the conduct of the authorities, often becomes complex in its application to individual cases, and will from time to time produce imperfect results, especially if one's attention is confined to the particular case at bar. Some criminals do go free because of the necessity of keeping government and its servants in their place. That is one of the costs of having and enforcing a Bill of Rights. This country is built on the assumption that the cost is worth paying, and that in the long run we are all both freer and safer if the Constitution is strictly enforced." —Williams v. Nix, 700 F. 2d 1164, 1173 (8th Cir. 1983) (Richard Sheppard Arnold, J.), rev'd Nix v. Williams, 467 US. 431 (1984).
"The criminal goes free, if he must, but it is the law that sets him free. Nothing can destroy a government more quickly than its failure to observe its own laws, or worse, its disregard of the charter of its own existence." —Mapp v. Ohio, 367 U.S. 643, 659 (1961).
"Any costs the exclusionary rule are costs imposed directly by the Fourth Amendment."
—Yale Kamisar, 86 Mich.L.Rev. 1, 36 n. 151 (1987).
"There have been powerful hydraulic pressures throughout our history that bear heavily on the Court to water down constitutional guarantees and give the police the upper hand. That hydraulic pressure has probably never been greater than it is today." — Terry v. Ohio, 392 U.S. 1, 39 (1968) (Douglas, J., dissenting).
"The great end, for which men entered into society, was to secure their property." —Entick v. Carrington, 19 How.St.Tr. 1029, 1066, 95 Eng. Rep. 807 (C.P. 1765)
"It is a fair summary of history to say that the safeguards of liberty have frequently been forged in controversies involving not very nice people. And so, while we are concerned here with a shabby defrauder, we must deal with his case in the context of what are really the great themes expressed by the Fourth Amendment." —United States v. Rabinowitz, 339 U.S. 56, 69 (1950) (Frankfurter, J., dissenting)
"The course of true law pertaining to searches and seizures, as enunciated here, has not–to put it mildly–run smooth." —Chapman v. United States, 365 U.S. 610, 618 (1961) (Frankfurter, J., concurring).
"A search is a search, even if it happens to disclose nothing but the bottom of a turntable." —Arizona v. Hicks, 480 U.S. 321, 325 (1987)
"For the Fourth Amendment protects people, not places. What a person knowingly exposes to the public, even in his own home or office, is not a subject of Fourth Amendment protection. ... But what he seeks to preserve as private, even in an area accessible to the public, may be constitutionally protected." —Katz v. United States, 389 U.S. 347, 351 (1967)
“Experience should teach us to be most on guard to protect liberty when the Government’s purposes are beneficent. Men born to freedom are naturally alert to repel invasion of their liberty by evil-minded rulers. The greatest dangers to liberty lurk in insidious encroachment by men of zeal, well-meaning but without understanding.” —United States v. Olmstead, 277 U.S. 438, 479 (1925) (Brandeis, J., dissenting)
“Liberty—the freedom from unwarranted intrusion by government—is as easily lost through insistent nibbles by government officials who seek to do their jobs too well as by those whose purpose it is to oppress; the piranha can be as deadly as the shark.” —United States v. $124,570, 873 F.2d 1240, 1246 (9th Cir. 1989)
"You can't always get what you want / But if you try sometimes / You just might find / You get what you need." —Mick Jagger & Keith Richards, Let it Bleed (album, 1969)
"In Germany, they first came for the communists, and I didn't speak up because I wasn't a communist. Then they came for the Jews, and I didn't speak up because I wasn't a Jew. Then they came for the trade unionists, and I didn't speak up because I wasn't a trade unionist. Then they came for the Catholics and I didn't speak up because I wasn't a Catholic. Then they came for me–and by that time there was nobody left to speak up."
—Martin Niemöller (1945) [he served seven years in a concentration camp]
“Children grow up thinking the adult world is ordered, rational, fit for purpose. It’s crap. Becoming a man is realising that it’s all rotten. Realising how to celebrate that rottenness, that’s freedom.” – John le Carré, The Night Manager (1993), line by Richard Roper
"The point of the Fourth Amendment, which often is not grasped by zealous officers, is not that it denies law enforcement the support of the usual inferences which reasonable men draw from evidence. Its protection consists in requiring that those inferences be drawn by a neutral and detached magistrate instead of being judged by the officer engaged in the often competitive enterprise of ferreting out crime." —Johnson v. United States, 333 U.S. 10, 13-14 (1948)
The book was dedicated in the first (1982) and sixth (2025) editions to Justin William Hall (1975-2025). He was three when this project started in 1978.
