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Talk to anyone lucky enough to earn his/her livelihood through criminal appellate practice, and you’ll likely hear some version of the following complaint: the Government is never held to the same standard as the criminal defendant on appeal.  Whether it’s waiver during the trial-level proceedings, or a purported waiver during oral argument or in the briefing, it often seems like appellate courts give the Government a degree of latitude that is not usually afforded to the defense.  This case is an exception and a refreshing reminder to the Government that not dotting i’s and crossing t’s can have some meaningful consequences.

In United States v. Reyes-Rivas, the defendant/appellant argued during sentencing and on appeal that he did not meet the criteria for a “career offender” enhancement under section 4B1.1 of the Sentencing Guidelines.  Specifically, he argued one of his priors – a Puerto Rico conviction for fourth degree aggravated battery – did not qualify as a “crime of violence.”  He also argued that the conviction could not qualify as a “crime of violence” under the residual clause of section 4B1.1.  He reasoned that the Supreme Court’s decision in Johnson v. United States, 135 S. Ct. 2551 (2015) applied to the career offender enhancement because the residual clause language in the Armed Career Criminal Act was almost identical to the residual clause language in the Sentencing Guidelines.

Michael Brownlee is board-certified as an appellate expert by the Florida Bar.  He is a First Circuit CJA attorney and practices in federal appellate courts around the country.  He is also the founding member of The Brownlee Law Firm.  To learn more, visit or email Mike at 

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Suppose a criminal defendant agrees to plead guilty and to waive the right to take an appeal or seek collateral review after being sentenced. Can the defendant nonetheless assert a claim of ineffective assistance at sentencing? A unanimous panel decision (Judges Srinivasan, Wilkins & Sentelle) held that such a claim may be raised—at least where the defendant executed a “generic” waiver that didn’t preclude a later-asserted claim of ineffectiveness.

The appellant pleaded guilty under such a generic plea agreement to one count of conspiracy to distribute five kilograms or more of cocaine on board an aircraft registered in the United States and one count of conspiracy to distribute and possess with intent to distribute 1,000 kilograms or more of marijuana. Unhappy with the sentence, Appellant claimed on direct appeal that his counsel below had failed to push for a minor role adjustment in the Sentencing Guidelines calculations and had rendered ineffective assistance. The Government was unsympathetic and urged that the waiver of appellate rights in the plea agreement precluded any assertion of ineffective assistance. (Slip Op. at 2-4).

The Court of Appeals looked first to United States v. Guillen, 561 F.3d 527, 529-30 (D.C. Cir. 2009), which upheld the validity of so-called “anticipatory waivers,” under which a defendant can validly waive her right to appeal a sentence that has not yet been imposed, as long as her decision is “knowing, intelligent, and voluntary.” (Slip Op. at 4). “As a general matter,” the Court of Appeals pointed out, ‘“an allegation that the sentencing judge misapplied the Sentencing Guidelines or abused his or her discretio is not subject to appeal in the face of a valid appeal waiver.’” (Slip Op. at 4-5) (quoting United States v. Adams, 780 F.3d 1182, 1184 -85 (D.C. Cir. 2015) (quoting United States v. Andis, 333 F.3d 886, 892 (8th Cir.  2003) (en   banc))). Applying those principles, Judge Srinivasan wrote, the Circuit has held that an appeal waiver barred a  defendant from appealing her sentence on the grounds that the district court: imposed a substantively unreasonable sentence, erroneously declined  to permit  the  defendant  to  introduce  certain  evidence at  sentencing  or  in  limiting  cross-examination  of  the  government’s  sentencing  witnesses,  or abused  its  discretion in denying  a  downward  variance from the sentencing guidelines range. (Slip Op. at 5) (citing Adams, 780 F.3d at 1184-85, and United States v. Ortega-Hernandez, 804 F.3d 447, 451 (D.C. Cir. 2015)).

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Following a Coast Guard interdiction of the Mistby, a Colombian vessel which was bringing cocaine and marijuana to Panama, the three defendants pleaded guilty to conspiring to distribute, and possess with intent to distribute, the drugs on board, in violation of the Maritime Drug Law Enforcement Act (“MDLEA”), 46 U.S.C. § 70501 et seq., and the Controlled Substances Import and Export Act, 21 U.S.C. § 951 et seq.

On appeal the defendants argued that they were not on board the vessel when it was intercepted and that the district court lacked subject-matter jurisdiction over their prosecutions because Colombia’s assent to U.S.jurisdiction over individuals associated with the ship supposedly was limited to persons found on board the vessel. Second, appellants contended that their offense of conviction was covered by the so-called safety-valve provision, 18 U.S.C. § 3553(f), which exempts covered offenses from mandatory-minimum sentences such as the 10-year terms each of them received.

The panel (Circuit Judges Srinivasan, Millett & Sentelle) concluded that the district court had subject-matter jurisdiction under the terms of the applicable treaty between the United States and Colombia, although none of the defendants had been aboard the ill-fated boat.

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Every May and June the black-robed folks down at 3rd and Constitution like to shake off DeeCee’s early summertime torpor by reversing some matters and announcing some new legal principles. This was Circuit Judges Griffith, Srinivasan and Wilkins’ turn.

Back in 2012, the Government began investigating a notorious drug dealer, Jermaine Washington, who had recently been released from prison. After employing traditional surveillance techniques, the Government successfully applied for two wiretaps on Washington’s cell phone. The evidence presented at appellants’ trial consisted largely of recorded conversations and Washington’s interpreting language in his conversations with the three defendants. A jury convicted Stoddard and Woodruff under 21 U.S.C. §§ 841(a)(1), 841(b)(1), and 846 for conspiracy to distribute and possess with intent to distribute heroin. It acquitted Jerome Cobble, Washington’s cousin, of those charges but convicted him on a separate charge of conspiracy to launder money in violation of 18 U.S.C. § 1956(h).

In an opinion authored by Circuit Judge Wilkins, the panel concluded that Cobble’s conviction of money laundering conspiracy was based on insufficient evidence. It overruled his colleagues’ merits-based appeals with one exception. It stated that for a defendant to be sentenced based on a mandatory minimum triggered by a certain quantity of drugs, a jury must find the drug quantity attributable to the defendant on an individualized basis, not just the drug quantity attributable to the conspiracy as a whole. And based on the intervening decision in Beckles v. United States, 137 S. Ct. 886 (2017), the panel instructed the district court on remand to re-examine the career-offender enhancement meted out to Woodruff. (Slip Op. at 1-2).

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Every time you are convinced you’re read it all, another one pops out of the hopper. Chief Judge Garland and Circuit Judges Kavanaugh and Millet’s’ eyeballs must have been bulging when they learned how the Government came across Dawayne (“Goon”) Brown and his associates in the PCP distribution trade. It turns out that one Louis Clifton walked into an MPD station and related what the per curiam decision describes as “an extraordinary story” that “[a]rmed men had taken over his apartment and were using the apartment to manufacture and sell PCP – all while Clifton continued to live there.” Mr. Clifton presented an account of enduring his unwelcome roommates, Mr. Brown and his friend, Keith Matthews, who were using his apartment for several weeks to make “dippers” of PCP-laced cigarettes and store the proceeds from selling dippers. The gendarmes then pounced and surprised Brown inside the apartment. They arrested him, seizing an Uzi, a .38-caliber revolver and PCP. (Slip Op. at 3-4).

An examination of Brown’s cell phone text messages led to Matthews’ arrest, at which point the police learned that the takeover of Clifton’s apartment was no isolated event. Brown, Matthews and several of their chums had created a PCP operation that they called “Little Mexico.” Little Mexico’s modus vivendi involved using Woodberry Village apartments to stash guns and sell PCP. (Slip Op. at 4-5).

Brown, Matthews and four others were indicted for narcotics conspiracy-related offenses. One, Ira Adona, pled guilty to the conspiracy charge. He was supposed to be sentenced separately in the Superior Court for a shooting offense and in the federal court for the PCP conspiracy.  (Two others pled guilty but didn’t appeal their sentences.)   Brown, Matthews and Marquette Boston stood trial and were duly convicted of drug and/or weapons charges. (Slip Op. at 5-6).

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Frederick (“Toby”) Miller was sentenced to terms of life imprisonment following RICO and narcotics conspiracy-related convictions that are reported in United States v. Eiland, 738 F.3d 338 (D.C. Cir. 2013) and, thanks to a hung jury in the first trial, in United States v. Miller, 738 F.3d 361 (D.C. Cir. 2013). On appeal from the first trial, the D.C. Circuit vacated various unlawful-use-of-a-communications-facility counts and affirmed the remaining counts. Miller, 738 F.3d at 387. On appeal from the second trial, the Circuit concluded that, although sufficient evidence supported Miller’s narcotics conspiracy conviction, the evidence failed to establish that he had organized or supervised five people as required for a CCE conviction. Eiland, 738 F.3d at 356–58. After affirming and reinstating Miller’s narcotics conspiracy conviction, the court vacated his sentence, and remanded the case for resentencing. Id. at 361. (Slip Op. at 7-8).

At resentencing, Miller again received a life sentence. He appealed once more and claimed, inter alia, that plain error had infected the Firearms and Role-in-the Offense enhancements, and that the District Court erred in stating that the Guidelines range for the RICO conspiracy was life, when it was in fact 360 months to life.  The Circuit Court of Appeals, in a decision written by Senior Circuit Judge Edwards, agreed and his case remanded for resentencing.

The Government fought Miller tooth-and-nail.  First, it raised two procedural defenses, the first centered around a theory that Miller had waived the enhancement claims by not making then before, and thus was barred by the law of the case doctrine from raising them at this point. These preliminary contentions, Judge Edwards retorted, were “seriously misguided.” (Slip Op. at 3-4). Miller’s “looming mandatory life sentence for his CCE conviction [had] rendered his present sentencing challenges fruitless” and “[g]iven this situation, Appellant was not obliged to raise arguments on his first appeal that were merely contingently relevant.” (Slip Op. at 4).

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Ineffective Assistance of Counsel–When the Sentencing Guidelines’ Language Controls the Commentary: United States v. Winstead, _ F.3d _ (D.C. Circuit, No. 12-3036 (May 25, 2018) 2018).

Winning an ineffective assistance of counsel claim on direct appeal is not an occurrence that happens frequently, much less through a decision that issued just seven weeks after oral argument. Aumbrey Winstead, a man with a (to be gentle) checkered past, was convicted of possession of a firearm (by a person convicted of a crime punishable by imprisonment of more than one year), possession with intent to distribute cocaine, and possession of a firearm during a drug trafficking offense. The evidence against him was, in the appellate panel’s word, “overwhelming.” (slip op. at 2). Thanks to nimble footwork by the Federal Defender’s Office, on direct appeal his thirty-year sentence as an Armed Career Criminal was found improper and his case remanded for resentencing.

First, a digression for a merits-based issue that crops up with sufficient frequency that defense counsel should place this case in their trial toolbox. Based on the Circuit’s decision in United States v. Sheffield, 832 F.3d 296, 307-08 (D.C. Cir. 2016), Mr. Winstead protested that pointed out that district judge’s decision to admit prior crimes as evidence of knowledge under Federal Rules 403 and 404(b) was error because the offenses were more than a decade old. The government, invoking out-of-circuit authority, responded that the staleness of old crimes is lessened if part of the time between the defendant’s old crime and a new case was spent in prison. The panel (Garland, C.J., Edwards and Silberman JJ), found that distinction intellectually troubling but concluded that the error – if any – of admitting this evidence was harmless given the overwhelming evidence of Winstead’s guilt. (Slip Op. at 7-9).

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United States v. Diaz, 884 F.3d 911 (9th Cir. 2018): Ninth Circuit remands for improper application of Sentencing Guidelines “minor role” adjustment

Once upon a time, teenage boys called “newsies” stood on street corners hawking newspapers. Each was a knowing and integral participants in the newspaper’s business, but each played only a “minor role” in the enterprise as a whole. Section 3B1.2(b) of the Sentencing Guidelines recommends that defendants who played such a “minor role” in a criminal enterprise should receive lesser sentences than more important players.

Can a drug courier be the drug-trafficking organization’s analog to the newsie? Alejandro Diaz thought so. After pleading guilty to importation of cocaine and heroin, Mr. Diaz argued that he was entitled to a minor-role adjustment in his sentence. The district refused to grant the adjustment. The Ninth Circuit held that this was error. The Ninth Circuit noted that to properly address the minor-role issue, the district court would have had to consider that Mr. Diaz was ignorant of the type and quantity of drugs concealed in the car he tried to drive across the border, that he knew only two other participants in the enterprise, and that he was to receive a set fee of $1,000 for his work and had no ownership interest or other stake in the outcome of the drug trafficking operation. Because the district court failed to take these pertinent facts into account, the Ninth Circuit vacated Mr. Diaz’s sentence and remanded the case for resentencing.

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How often does one see a multiplicity victory? Not that often. Gary Cooper (per Judge Henderson, “not that one”), was convicted on a five-count indictment for his role in a scheme to steal from a labor union. On appeal, he successfully argued that the two charges (18 U.S.C. were in effect one and the same and therefore multiplicitous.  Because his sentence rested on an erroneous application of a U.S.S.G. § 2E5.1(b)(1) enhancement, Mr. Cooper pointed out that it was further marred. And finally, Mr. Cooper added that his 68-month sentences exceeded the statutory maximum provided for the conspiracy, wire fraud and honest services fraud counts (18 U.S.C. §§ 371, 1343, 1346)

In agreeing with Mr. Cooper, the panel (Henderson, Tatel and Williams, JJ) first examined the standard of review. Brushing aside the Government’s insistence that the multiplicity argument was forfeited, Judge Henderson found that the defense’s pretrial motion to dismiss (Rule 12(b), FED. R. CRIM. P.)  preserved the issue . (Slip. Op. at 8-9).

Moving on, and applying a de novo standard of review, Judge Henderson examined the two conspiracy counts to determine whether two counts of the same indictment charged a violation of the general conspiracy statute, 18 U.S.C. § 371?  “The question is, then, whether the counts charge ‘the same act or transaction”—i.e., the same conspiracy—at all.   (Slip. Op. at 10) (quoting and citing Blockburger v. United States, 284 U.S. 299, 304 (1932); Braverman v. United States, 317 U.S. 49,  52,54 (1942) (conspiracy  counts  are  multiplicitous  if  they  charge same agreement  under same conspiracy  statute); Ward  v. United States, 694 F.2d 654, 661 (11th Cir. 1983) (same, citing additional cases)).  Referring to United States v. Gatling, 96 F.3d 1151, 1152 (D.C. Cir. 1996), and applying the test used for double jeopardy case, viz., allegations of “common purpose, overlaps of participants and time, location where acts occurred, and interdependence,” the Circuit found that “[h]ere, all the factors point in the same direction: Counts One and Two charged the same conspiracy.” (Slip Op. at 11).

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United States v. Laney, __ F.3d __, 2018 WL 706497 (9th Cir. Feb. 5, 2018): Stipulations bearing only counsel’s e-signatures failed to show that defendants knowingly waived their right to a jury trial

Federal courts often remind us that they must “indulge every reasonable presumption against waiver of fundamental constitutional rights,” and that such waivers must be “voluntary, knowing, and intelligent” to be effective. What to do, then, when the only record confirmation that two fraud defendants waived their right to a jury trial consists of two stipulations bearing their lawyers’ electronic signatures?

Reverse, that’s what.

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