2255 petitioner’s IAC claim of ineffectiveness in a plea agreement with a collateral review provision premised on a failure to recognize a Fourth Amendment claim was sufficient. Hurlow v. United States, 726 F.3d 958 (7th Cir. 2013):
The same is true for a petitioner such as Hurlow who seeks to overcome the waiver provision in his plea agreement based on ineffective assistance of counsel: he cannot just assert that a constitutional violation preceded his decision to plead guilty or that his trial counsel was ineffective for failing to raise the constitutional claim. Rather, he must allege that he entered the plea agreement based on advice of counsel that fell below constitutional standards. In other words, he must allege that the plea agreement was “the product of ineffective assistance of counsel,” Jemison, 237 F.3d at 916 n.8, or “tainted by ineffective assistance of counsel,” United States v. Henderson, 72 F.3d 463, 465 (5th Cir. 1995). See also United States v. Teeter, 257 F.3d 14, 25 n.9 (1st Cir. 2001) (“This category [of situations in which denying a right of appeal would work a miscarriage of justice] is infinitely variable, but, by way of illustration, we would include within it situations in which appellants claim … that the plea proceedings were tainted by ineffective assistance of counsel.” (citations omitted)); DeRoo v. United States, 223 F.3d 919, 924 (8th Cir. 2000) (“[W]aiver of the right to seek section 2255 post-conviction relief does not waive defendant’s right to argue, pursuant to that section, that the decision to enter into the plea was not knowing and voluntary because it was the result of ineffective assistance of counsel”). For example, in United States v. Cieslowski, the defendant’s plea agreement contained a waiver of direct and collateral review, but the defendant claimed that his decision to enter into that plea agreement was the product of his attorney’s ineffectiveness in “fail[ing] to file two suppression motions[.]” 410 F.3d at 358, 360. Because this claim was the sort that, “if successful, would result in setting aside the plea agreement as a whole,” we considered (and ultimately rejected) the defendant’s ineffective assistance of counsel argument on the merits. Id. at 361.
Turning to Hurlow’s allegations in his § 2255 petition, we similarly conclude that they are sufficient to overcome the waiver in his plea agreement. First, he alleged that his trial counsel was ineffective by failing to recognize that the detectives who obtained the critical evidence against him did so in violation of the Fourth Amendment: even though Hurlow apprised him of facts that indicated that the search violated Georgia v. Randolph, counsel refused to listen or investigate further. See Tollet, 411 U.S. at 266-67 (“Counsel’s failure to evaluate properly facts giving rise to a constitutional claim, or his failure properly to inform himself of facts that would have shown the existence of a constitutional claim, might in particular fact situations meet this standard of proof.”). Second, Hurlow alleged that his decision to plead guilty resulted from counsel’s ineffectiveness. According to Hurlow, counsel failed to inform him that a challenge to the search was possible, and instead “persuaded” and “cajoled” him into pleading guilty by telling him “that if [he] did not plead guilty, that [he] would [receive] 30 years to life imprisonment.” Hurlow alleged that had he known he could “contest the unconstitutional and unreasonable search[,]” he “would not have entered into the one-sided government authorized plea agreement” or “pled guilt[.]” Thus, Hurlow is saying that he would not have agreed to the terms of the plea agreement had his counsel informed him of his potentially meritorious Fourth Amendment claim. Cf. Cieslowski, 410 F.3d at 360 (“He does not say, however, that he would have not pleaded guilty but for the erroneous advice.”). This is sufficient to overcome the collateral review waiver in his plea agreement.
This entry was posted in Uncategorized. Bookmark the permalink.
"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.