United States v. Cuthbertson ( 2020 )


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  •                                                                          FILED
    United States Court of Appeals
    Tenth Circuit
    UNITED STATES COURT OF APPEALS October 28, 2020
    Christopher M. Wolpert
    TENTH CIRCUIT                       Clerk of Court
    UNITED STATES OF AMERICA,
    Plaintiff - Appellee,
    No. 18-1223
    v.                                           (D.C. Nos. 1:18-CV-00173-REB &
    1:16-CR-00204-REB-DW-1)
    LEVON DANIEL CUTHBERTSON,                                (D. Colo.)
    Defendant - Appellant.
    ORDER AND JUDGMENT *
    Before BRISCOE, HOLMES, and MATHESON, Circuit Judges.
    Defendant-Appellant Levon Daniel Cuthbertson appeals from the district
    court’s denial of his motion to vacate his sentence under 
    28 U.S.C. § 2255
    . We
    granted a certificate of appealability (“COA”) on Mr. Cuthbertson’s ineffective-
    assistance-of-counsel claim. Mr. Cuthbertson argues that his trial counsel was
    ineffective for failing to argue that Hobbs Act robbery does not qualify as a crime
    *
    This order and judgment is not binding precedent, except under the
    doctrines of law of the case, res judicata, and collateral estoppel. It may be cited,
    however, for its persuasive value consistent with Federal Rule of Appellate
    Procedure 32.1 and 10th Circuit Rule 32.1. After examining the briefs and
    appellate record, this panel has determined unanimously that oral argument would
    not materially assist in the determination of this appeal. See F ED . R. A PP . P.
    34(a)(2); 10 TH C IR . R. 34.1(G). The case is therefore ordered submitted without
    oral argument.
    of violence under § 4B1.2(a) of the United States Sentencing Guidelines
    (“U.S.S.G.” or the “Guidelines”) because it proscribes threats against property.
    We agree. Exercising jurisdiction under 
    28 U.S.C. §§ 1291
     and 2253(a), we
    reverse the district court’s order denying Mr. Cuthbertson’s § 2255 motion and
    remand the case with instructions to vacate his sentence and resentence him.
    I
    In 2016, Mr. Cuthbertson pleaded guilty to two counts of being a felon in
    possession of a firearm, pursuant to 
    18 U.S.C. § 922
    (g)(1). His presentence
    report (“PSR”) listed his base offense level as 20—a six-level increase from the
    usual offense level of 14. 1 The PSR applied the enhancement because Mr.
    Cuthbertson purportedly had a prior felony conviction for a crime of
    violence—specifically, Hobbs Act robbery. See U.S.S.G. § 2K2.1(a)(4)(A)
    (applying a base offense level of 20 to unlawful-possession violations where the
    1
    The U.S. Probation Office used the 2016 edition of the Guidelines in
    calculating Mr. Cuthbertson’s sentence. Trial counsel objected to the use of the
    2016 edition. Counsel argued that use of the 2016 Guidelines, instead of the
    Guidelines in effect at the date of Mr. Cuthbertson’s offense, “would violate the
    ex post facto clause of the U.S. Constitution.” R., Vol. I, at 30 (Def.’s Objection
    to Presentence Report, dated Mar. 17, 2017). However, in the Defendant’s
    Objection to the Presentence Report, trial counsel did not explain why using the
    2016 Guidelines would violate the Ex Post Facto Clause of the U.S. Constitution.
    On appeal, Mr. Cuthbertson has not raised this particular argument, so we will not
    consider it.
    2
    defendant has a prior felony conviction for a “crime of violence”). U.S.S.G.
    § 4B1.2(a) defines “crime of violence” as:
    (a)   [A]ny offense under federal or state law, punishable by
    imprisonment for a term exceeding one year, that—
    (1)    has as an element the use, attempted use, or
    threatened use of physical force against the person
    of another [i.e., the elements clause], or
    (2)    is murder, voluntary manslaughter, kidnapping,
    aggravated assault, a forcible sex offense, robbery,
    arson, extortion, or the use or unlawful possession
    of a firearm described in 
    26 U.S.C. § 5845
    (a) or
    explosive material as defined in 
    18 U.S.C. § 841
    (c)
    [i.e., the enumerated-offenses clause].
    Mr. Cuthbertson’s counsel objected to the PSR recommendation, arguing
    that Hobbs Act robbery is not a crime of violence under § 4B1.2(a) because it can
    be committed with de minimis force and it does not require the use of physical
    force. The government responded with two counter-arguments for why Hobbs
    Act robbery is a crime of violence: first, it involves the necessary amount of
    physical force to qualify under the elements clause, § 4B1.2(a)(1); and second, it
    qualifies as generic robbery under the enumerated-offenses clause, § 4B1.2(a)(2).
    Notably, the government did not argue that Hobbs Act robbery is “extortion”
    under the enumerated-offenses clause. Mr. Cuthbertson’s trial counsel did not
    reply to the government’s arguments in writing. At sentencing, he merely
    reiterated the same arguments he had already made in his objection to the PSR.
    3
    The district court sided with the government and held that Hobbs Act
    robbery is a crime of violence under both the elements and enumerated-offenses
    clauses. Consequently, the applicable Guidelines range was 84-to-105 months’
    imprisonment instead of 46-to-57 months. The district court ultimately sentenced
    Mr. Cuthbertson to 87 months’ imprisonment. He did not file a direct appeal.
    Six months later, we decided United States v. O’Connor, 
    874 F.3d 1147
    (10th Cir. 2017). In O’Connor, we held that Hobbs Act robbery is not a
    Guidelines crime of violence under either the elements or the enumerated-
    offenses clauses of § 4B1.2(a). See 874 F.3d at 1158. We concluded that Hobbs
    Act robbery is not categorically a crime of violence under the elements clause
    because it “criminalizes conduct involving threats to property,” id., whereas the
    elements clause is limited to the “use, attempted use, or threatened use of physical
    force against the person of another,” id. at 1150 (emphasis added). And we found
    that Hobbs Act robbery is not categorically a crime of violence under the
    enumerated-offenses clause as “robbery” because it “encompasses threats to
    property,” whereas “generic robbery excludes threats that are limited to property.”
    Id. at 1155. 2
    2
    We further held that Hobbs Act robbery also was not “extortion”
    under the enumerated-offenses clause. We determined that reasonable minds
    could disagree over whether “extortion” in § 4B1.2(a)(2) included threats to
    property. O’Connor, 874 F.3d at 1156–57. Thus, we found that the definition of
    (continued...)
    4
    Following our decision in O’Connor, Mr. Cuthbertson received a letter
    from an attorney in the Office of the Federal Public Defender for Colorado
    claiming that his trial counsel’s performance was constitutionally ineffective for
    failing to argue “that crimes of violence have to involve violence against a person
    or that Hobbs Act [r]obbery can be committed by using violence against
    property.” R., Vol. I, at 75 (Ex. A to § 2255 Pet., filed Jan. 22, 2018). The letter
    attributed this failure by trial counsel to “sloppiness and negligence.” Id. at 76.
    The author of the letter was not Mr. Cuthbertson’s trial counsel. After receiving
    the letter, Mr. Cuthbertson filed a pro se motion to vacate under 
    28 U.S.C. § 2255
    , claiming ineffective assistance of counsel on the same grounds explained
    in the letter.
    The district court denied the motion, holding that “[c]ounsel cannot be
    deemed to have been constitutionally ineffective because counsel failed to divine
    at the time of sentencing the future holding of the Tenth Circuit in [O’Connor].”
    
    Id. at 98
     (Dist. Ct. Order, dated Apr. 19, 2018). The court then denied Mr.
    Cuthbertson’s request for a COA. The court also certified under 
    28 U.S.C. § 1915
    (a)(3) that any appeal from the order would not be taken in good faith, and
    2
    (...continued)
    extortion was ambiguous, and we applied the rule of lenity to interpret it to
    exclude threats of injury to property. 
    Id.
     at 1157–58. As a result, we concluded
    that Hobbs Act robbery categorically exceeds the extortion offense under the
    enumerated-offenses clause. 
    Id. at 1158
    .
    5
    it denied Mr. Cuthbertson’s motion for leave to proceed in forma pauperis. 
    Id.
     at
    98–99. Mr. Cuthbertson filed a notice of appeal.
    On appeal, Mr. Cuthbertson argues, inter alia, that trial counsel was
    constitutionally ineffective for failing to argue that Hobbs Act robbery
    categorically exceeds both the elements and enumerated-offenses clauses because
    it can be committed against property. See Aplt.’s Opening Br. and Request for a
    COA at 14–30. We issued a COA on this ineffective-assistance-of-counsel claim.
    II
    Mr. Cuthbertson claims that trial counsel was constitutionally ineffective
    for failing to argue that Hobbs Act robbery is not a crime of violence because it
    extends to threats against property. We respond in the following steps. First, we
    explain the standard of review and the standard for claims of ineffective
    assistance of counsel announced in Strickland v. Washington, 
    466 U.S. 668
    (1984). Second, we agree that counsel was constitutionally deficient for failing to
    argue that Hobbs Act robbery is not a crime of violence under both the elements
    and enumerated-offenses clauses because it extends to threats against property.
    Third, we hold that counsel’s failure to raise these arguments prejudiced Mr.
    Cuthbertson.
    6
    A
    “In reviewing denial of a § 2255 motion for post-conviction relief where a
    COA has been granted, ‘we review the district court’s findings of fact for clear
    error and its conclusions of law de novo.’” United States v. Viera, 
    674 F.3d 1214
    ,
    1217 (10th Cir. 2012) (quoting United States v. Rushin, 
    642 F.3d 1299
    , 1302
    (10th Cir. 2011)). “A claim for ineffective assistance of counsel presents a mixed
    question of fact and law, which we review de novo.” United States v. Orange,
    
    447 F.3d 792
    , 796 (10th Cir. 2006).
    To succeed on an ineffective assistance of counsel claim, Mr. Cuthbertson
    must satisfy the two-part test set out in Strickland. Under the first part of the test,
    Mr. Cuthbertson must show that trial counsel was “deficient,” i.e., that counsel’s
    “representation fell below an objective standard of reasonableness” as measured
    by “prevailing professional norms.” Strickland, 
    466 U.S. at 688
    ; see also Harris
    v. Sharp, 
    941 F.3d 962
    , 973 (10th Cir. 2019) (“Attorneys are deficient [under
    Strickland] when their mistakes are so serious that they stop functioning as
    ‘counsel’ for purposes of the Sixth Amendment.”). Under the second part of the
    Strickland test, Mr. Cuthbertson must show “prejudice,” i.e., “a reasonable
    probability that, but for counsel’s unprofessional errors, the result of the
    proceeding would have been different.” 
    466 U.S. at 694
    . We conclude that Mr.
    Cuthbertson has succeeded in meeting this burden.
    7
    B
    Mr. Cuthbertson argues that trial counsel was constitutionally deficient for
    failing to argue that Hobbs Act robbery is not a crime of violence—under either
    the elements or enumerated-offenses clauses—because it extends to threats
    against property. The government replies that trial counsel was not deficient for
    failing to make these arguments because at the time of sentencing “no court had
    held that Hobbs Act robbery’s inclusion of threats to property placed it outside
    the crime of violence definition.” Aplee.’s Resp. Br. at 7. The government
    insists that “[b]ecause effective representation does not require clairvoyance,
    counsel is not ineffective for ‘failing to predict future law’”—specifically, our
    holding in O’Connor. Aplee.’s Resp. Br. at 10 (quoting Bullock v. Carver, 
    297 F.3d 1036
    , 1052 (2002)); see Sherill v. Hargett, 
    184 F.3d 1172
    , 1175 (10th Cir.
    1999) (“Generally, counsel is not ineffective for failing to anticipate arguments or
    appellate issues that only blossomed after defendant’s trial and appeal have
    concluded.”).
    Nonetheless, Mr. Cuthbertson argues that effective counsel would have
    been aware of these arguments at the time of sentencing because (1) it was
    obvious from the text of the statute that Hobbs Act robbery did not categorically
    fall within the elements clause, and (2) we previously had “strongly suggested” in
    United States v. Castillo, 
    811 F.3d 342
    , 347 (10th Cir. 2015), that “generic
    robbery is limited to threats against a person.” O’Connor, 874 F.3d at 1154. We
    8
    agree with Mr. Cuthbertson.
    1
    Mr. Cuthbertson first contends that trial counsel was constitutionally
    deficient for failing to argue that Hobbs Act robbery is not a crime of violence
    under the elements clause because it extends to threats against property. We
    agree and hold that reasonably competent counsel would have been aware of the
    argument and would not have failed to make it.
    In Heard v. Addison, we concluded that when the breadth of a statute was
    “constitutionally suspect,” “minimally competent counsel would have recognized a
    likely defense based on the statute’s text” alone. 
    728 F.3d 1170
    , 1180 (10th Cir.
    2013) (emphasis added). We further held that, “[h]aving reached such a
    conclusion, any minimally competent lawyer would then have turned to case law to
    determine whether the . . . statute’s reach . . . had somehow [been] limited.” 
    Id.
     If
    “no narrowing construction” is found, we concluded that “minimally competent
    counsel would have recognized the possibility of asserting viable defenses to
    culpability under the statute.” 
    Id.
    As in Heard, we hold that effective counsel would have recognized a likely
    defense to the application of the crime-of-violence enhancement based on the text
    of § 4B1.2(a) alone. By its very terms, Hobbs Act robbery exceeds the scope of
    the elements clause. Hobbs Act robbery is “fear of injury, immediate or future, to
    [the victim’s] person or property.” 
    18 U.S.C. § 1951
    (b)(1) (emphasis added). Yet
    9
    the elements clause is explicitly limited to crimes that have “as an element the use,
    attempted use, or threatened use of physical force against the person of another.”
    U.S.S.G. § 4B1.2(a)(1) (emphasis added). In that way, the scope of Hobbs Act
    robbery categorically exceeds the scope of “crimes of violence” under the elements
    clause.
    Having recognized this potential defense, effective counsel would “have
    turned to case law to determine whether” the courts had foreclosed “the possibility
    of asserting it.” Heard, 728 F.3d at 1180. The government points to three groups
    of cases supposedly undermining this defense based on the distinction between an
    offense against a person and property. We hold that none of the three groups of
    cases undermined the potential person/property defense to the point that
    “minimally competent counsel would [not] have recognized the possibility of
    asserting [it].” Id.
    The first group consists of two cases holding that robbery under Colorado
    state law satisfies the elements clause of § 4B1.2(a) and the identical elements
    clause of the Armed Career Criminal Act. See United States v. Crump, 674 F.
    App’x 802, 803 (10th Cir. 2017) (unpublished); United States v. Harris, 
    844 F.3d 1260
    , 1270 (10th Cir. 2017). Yet the person/property distinction was not at issue
    in either case. Instead, both defendants argued that robbery under Colorado law
    did not satisfy the “physical force” factor of the elements clause. See Harris, 844
    F.3d at 1264 (“Harris limits his challenge to the elements clause’s ‘physical force’
    10
    component.”); Crump, 674 F. App’x at 803 (applying Harris to reverse the district
    court’s ruling that robbery in Colorado did not satisfy the elements clause in
    § 4B1.2(a)(1) “because robbery does not necessarily require the use or threatened
    use of physical force” (emphasis added)). Moreover, in Harris, the panel relied on
    the fact that Colorado Supreme Court precedent “undermine[d] the position that
    Colorado would prosecute threats against property, or intimidation by means not
    implicating bodily harm, as robbery.” 844 F.3d at 1270. The Harris panel thus
    concluded that Colorado robbery “has as an element the use or threatened use of
    physical force against another person.” Id. And Crump, decided by the same
    panel on the same day, relied on Harris to reach the same conclusion. 674 F.
    App’x at 803. Thus, Crump and Harris in no way undermine the person/property
    defense.
    The second group of cases consists of two Eighth Circuit decisions. These
    cases purportedly stand for the proposition that Hobbs Act robbery falls within the
    elements clause of 
    18 U.S.C. § 3559
    (c)(2)(f)(ii), which, like the elements clause of
    § 4B1.2(a)(1), requires the use or threat of physical force against a person. See
    United States v. Farmer, 
    73 F.3d 836
    , 842 (8th Cir. 1996); United States v. House,
    
    825 F.3d 381
    , 386–87 (8th Cir. 2016). But see United States v. Eason, 
    953 F.3d 1184
    , 1190 (11th Cir. 2020) (casting doubt on whether either Farmer or House
    may be construed as basing their holding solely on the alleged congruence between
    Hobbs Act robbery and § 3559(c)(2)(f)(ii)’s elements clause). These cases,
    11
    however, are neither binding nor persuasive. They are not binding because they
    are out-of-circuit, and they are not persuasive because they reach their holdings
    without much meaningful analysis and, more importantly, without any analysis
    whatsoever of the person/property defense at issue here. See Farmer, 
    73 F.3d at 842
    ; House, 825 F.3d at 386–87.
    The final group consists of cases from multiple circuits, including this one,
    holding that Hobbs Act robbery qualifies as a crime of violence under the elements
    clause of 
    18 U.S.C. § 924
    (c)(3)(A). See United States v. Anglin, 
    846 F.3d 954
    ,
    965 (7th Cir. 2017) (noting the “unbroken consensus” of circuits that have
    considered whether Hobbs Act robbery is a crime of violence under the elements
    clause of 
    18 U.S.C. § 924
    (c)(3)(A)), vacated on other grounds, 
    138 S. Ct. 126
    (2017); see also United States v. Moreno, 665 F. App’x 678, 681 (10th Cir. 2016)
    (unpublished) (holding that Hobbs Act robbery is a crime of violence under the
    elements clause of § 924(c)(3)(A)). Yet these cases also do not undermine the
    person/property defense. As the government itself admits, the elements clause of
    § 924(c)(3)(A)—unlike the elements clause of § 4B1.2(a)(1)—explicitly includes
    the use of force against property. See O’Connor, 874 F.3d at 1158 (“There is
    nothing incongruous about holding that Hobbs Act robbery is a crime of violence
    for purposes of 
    18 U.S.C. § 924
    (c)(3)(A), which includes force against a person or
    property, but not for purposes of U.S.S.G. § 4B1.2(a)(1), which is limited to force
    against a person.”).
    12
    Because none of these three groups of cases foreclosed the person/property
    defense, we hold that “minimally competent counsel would have recognized the
    possibility of asserting” it. Heard, 728 F.3d at 1180.
    As we further recognized in Heard, “our determination that constitutionally
    sufficient counsel would have become aware of the defense and cases we have
    discussed does not end our inquiry.” Id. at 1182. We must still determine whether
    competent counsel, after becoming aware of the person/property defense, could
    have reasonably chosen not to raise it. As the government points out, counsel is
    not required to raise every meritorious claim, see Kimmelman v. Morrison, 
    477 U.S. 365
    , 382 (1986), and may reasonably decide not to raise a “colorable”
    argument to avoid watering down a stronger one, Jones v. Barnes, 
    463 U.S. 745
    ,
    753 (1983) (“A brief that raises every colorable issue runs the risk of burying good
    arguments . . . in a verbal mound made up of strong and weak contentions.”).
    Moreover, Strickland imposes a strong presumption that a counsel made a later-
    disputed decision “in the exercise of reasonable professional judgment.” 
    466 U.S. at 690
    .
    In spite of the heavy burden imposed by Strickland, we hold that counsel
    was constitutionally deficient for failing to argue that Hobbs Act robbery is not a
    crime of violence under the elements clause because it extends to threats against
    property. Stated otherwise, Mr. Cuthbertson’s counsel represented him in an
    objectively unreasonable manner when he failed to argue the person/property
    13
    defense. Although it is true that counsel may reasonably choose not to raise a
    colorable argument to risk diverting attention away from stronger ones, we “may
    not indulge ‘post hoc rationalization’ for counsel’s decisionmaking that contradicts
    the available evidence of counsel’s actions.” Richter, 562 U.S. at 109 (quoting
    Wiggins v. Smith, 
    539 U.S. 510
    , 526–527 (2003)). Here, trial counsel raised two
    weaker arguments for why Hobbs Act robbery is not a crime of violence under the
    elements clause: specifically, (1) that it can be committed by de minimis force, and
    (2) that it can be committed by threatening force that is not physical. We cannot
    conclude that reasonable counsel would have chosen to forgo the person/property
    defense to avoid watering down these two weaker defenses. Thus, Mr.
    Cuthbertson has met his first-prong Strickland burden of showing that his
    counsel’s representation was objectively unreasonable—viz., reasonable counsel
    would not have failed to argue that Hobbs Act robbery is not a crime of violence
    under the elements clause because it proscribes threats against property.
    2
    Next, Mr. Cuthbertson argues that trial counsel was constitutionally
    deficient for failing to argue that Hobbs Act robbery is not a crime of violence
    under the enumerated-offenses clause because it categorically exceeds generic
    robbery, also by extending to threats against property. We agree.
    Effective trial counsel would have had several reasons for knowing that
    Hobbs Act robbery is broader than generic robbery under the enumerated-offenses
    14
    clause. First, and most importantly, effective counsel would have looked to
    language in United States v. Castillo, 
    811 F.3d 342
     (10th Cir. 2015). The
    defendant in Castillo argued that his conviction for robbery under California law
    was not a crime of violence under U.S.S.G. § 4B1.2(a), and thus the district court
    erred in applying a sentencing enhancement. In our decision, we acknowledged
    the defendant’s argument that “the weight of authority and the vast majority of
    state criminal codes require a threat to a person, not merely to property, to
    constitute robbery.” Id. at 346. We also highlighted the government’s concession
    that including threats to property in “the generic definition of robbery . . . is ‘the
    minority position’ in state criminal codes.” Id. But we nonetheless still concluded
    that the robbery was a crime of violence under U.S.S.G. § 4B1.2(a) because it
    amounted to “extortion” under the enumerated-offenses clause. However, that
    ultimate holding hardly diminishes the otherwise strong implication of our
    language on generic robbery in U.S.S.G. § 4B1.2(a)—the implication that the
    reach of this offense does not extend beyond threats against persons. Indeed, that
    reasonable counsel should have discerned this meaning from Castillo’s text was
    expressly recognized later in O’Connor, where we observed the following: “We
    strongly suggested that generic robbery is limited to threats against a person in
    Castillo, although our holding did not rely on it.” 874 F.3d at 1154.
    Moreover, as telling as it is, effective counsel need not have relied solely on
    the plain text of Castillo for support for this elements-clause argument. For
    15
    example, in an unpublished Tenth Circuit panel concurrence, one of our
    colleagues, addressing Castillo, commented that “Mr. Castillo was correct about
    the differences between the California robbery statute and generic robbery.”
    United States v. Aguilar-Ramos, 645 F. App’x 777, 779 (10th Cir. 2016) (McHugh,
    J., concurring). In that way, the panel concurrence foreshadowed the conclusion
    we reached in O’Connor.
    Effective counsel also could have found support in an analogous holding by
    the Ninth Circuit in United States v. Becerril-Lopez, 
    541 F.3d 881
     (9th Cir. 2008).
    The question presented in that case was whether robbery under California law is a
    crime of violence as defined in U.S.S.G. § 2L1.2, a portion of the Guidelines on
    unlawfully entering or remaining in the United States. As in U.S.S.G. § 4B1.2(a),
    one of the enumerated offenses under U.S.S.G. § 2L1.2 is robbery. The Ninth
    Circuit concluded that robbery under California law “is broader than generic
    robbery [under U.S.S.G. § 2L1.2] . . . because it encompasses takings
    accomplished by a broader range of threats than would the generic offense.”
    Becerril-Lopez, 
    541 F.3d at 891
    . That is, robbery under California law is “broader
    because it encompasses mere threats to property, such as ‘Give me $10 or I’ll key
    your car’ or ‘Open the cash register or I’ll tag your windows.’ [California state-
    law robbery] is not, therefore, categorically ‘robbery’ as used in the [U.S.S.G.
    § 2L1.2].” Id.
    16
    In short, effective counsel would have been aware of this elements-clause
    argument, which was strongly suggested in a published Tenth Circuit case,
    acknowledged in an unpublished Tenth Circuit panel concurrence, and actually
    adopted in an analogous context in a published out-of-circuit case. Cf. Heard, 728
    F.3d at 1182, 1184 (holding that counsel was constitutionally ineffective, in a state
    court trial, for failing to discover two “unpublished decisions” by the state’s
    highest court of criminal appeals); United States v. Demeree, 108 F. App’x 602,
    605 (10th Cir. 2004) (unpublished) (holding that counsel was constitutionally
    ineffective for failing to make an argument even though “we had not yet addressed
    the issue and our sister circuits were divided”). We therefore hold that effective
    counsel would have been aware of the person/property defense to the
    government’s claim that Hobbs Act robbery is a crime of violence under the
    enumerated-offenses clause.
    Yet, as previously discussed, “our determination that constitutionally
    sufficient counsel would have become aware of the possible defenses and cases we
    have discussed does not end our inquiry.” Heard, 728 F.3d at 1182. But we
    conclude that Mr. Cuthbertson has successfully shouldered his burden of
    demonstrating that it was objectively unreasonable representation for Mr.
    Cuthbertson’s counsel to fail to argue that Hobbs Act robbery is not generic
    robbery under U.S.S.G. § 4B1.2(a)(2) because it extends to threats against
    property.
    17
    The government argues that counsel could have reasonably chosen not to
    raise the defense to avoid relying on Castillo and Becerril-Lopez. According to
    the government, relying on these cases would have alerted the court to an
    alternative ground on which to rule for the government—namely, that Hobbs Act
    robbery is a crime of violence because it falls within the enumerated offense of
    extortion.
    We disagree. Prior to Mr. Cuthbertson’s sentencing hearing, the Sentencing
    Commission amended the Guidelines to include a definition of the term
    “extortion.” See U.S.S.G. § 4B1.2 cmt. n.1 (2016) (“‘Extortion’ is obtaining
    something of value from another by the wrongful use of (A) force, (B) fear of
    physical injury, or (C) threat of physical injury.”). In doing so, the Commission
    supplanted the prior generic definition of extortion in U.S.S.G. § 4B1.2(a)(2) with
    a new and narrower one. See O’Connor, 874 F.3d at 1156 (“We need not derive a
    generic definition of extortion because the Guidelines provide the applicable
    definition in Amendment 798, effective as of August 1, 2016,” which
    “‘narrow[ed]’ the long-standing generic definition of extortion.” (quoting
    Amendment 798 at 131)). Thus, at the moment of Mr. Cuthbertson’s sentencing,
    Castillo and Becerril-Lopez—which held that robbery committed by threats to
    property is generic extortion—were irrelevant to whether robbery committed by
    threats to property was extortion under U.S.S.G. § 4B1.2(a)(2). As a result, it
    would have been unreasonable for counsel to fail to argue that Hobbs Act robbery
    18
    is broader than generic robbery just so he could avoid relying on Castillo and
    Becerril-Lopez.
    ***
    Mr. Cuthbertson has shown that counsel—providing objectively reasonable
    representation—would not have failed to argue that Hobbs Act robbery is not a
    crime of violence, under both the elements and enumerated-offenses clauses,
    because it extends to threats against property. Mr. Cuthbertson therefore has met
    his burden under the first part of the Strickland test.
    C
    We now turn to the second part of the Strickland test, whether the
    ineffective assistance of counsel prejudiced Mr. Cuthbertson. Here we ask
    whether there is “a reasonable probability that, but for counsel’s unprofessional
    errors, the result of the proceeding would have been different.” Strickland, 
    466 U.S. at 694
    . We hold that Mr. Cuthbertson did suffer prejudice as a result of trial
    counsel’s failure to argue that Hobbs Act robbery is not a crime of violence
    because it extends to threats against property.
    “When, as here, the basis for the ineffective assistance claim is the failure to
    raise an issue, we must look to the merits of the omitted issue” to determine
    whether that failure was prejudicial. Orange, 
    447 F.3d at 797
    . Here, the omitted
    arguments were wholly meritorious, as shown by our two-fold holding in
    O’Connor that: “one can commit Hobbs Act robbery by threatening property
    19
    alone”; and a “generic robbery is limited to the use or threat of force against a
    person, and thus a robbery statute that punishes the use or threat of force against
    property exceeds the generic robbery definition.” O’Connor, 874 F.3d at 1153–54.
    This leaves no doubt that the omitted arguments—on both the elements and
    enumerated-offenses clauses—were meritorious, and we conclude that there is a
    reasonable probability that raising the arguments would have altered the outcome
    of the proceedings. Thus, we hold that trial counsel’s failure to raise them was
    prejudicial.
    III
    For the foregoing reasons, we hold that Mr. Cuthbertson has successfully
    established a violation of his Sixth Amendment right to counsel. Consequently,
    we REVERSE the district court’s denial of his motion under 
    28 U.S.C. § 2255
    and REMAND the case to the district court with instructions to VACATE Mr.
    Cutherbertson’s sentencing judgment and resentence him. 3
    ENTERED FOR THE COURT
    Jerome A. Holmes
    Circuit Judge
    3
    Mr. Cuthbertson’s motion to proceed in forma pauperis is granted.
    20