                               In the

    United States Court of Appeals
                 For the Seventh Circuit
No. 14-2242

UNITED STATES OF AMERICA,
                                                   Plaintiff-Appellee,

                                  v.


CARL MORRIS,
                                                Defendant-Appellant.

         Appeal from the United States District Court for the
                    Western District of Wisconsin.
         No. 3:14-cr-00029-bbc-1— Barbara B. Crabb, Judge.


   ARGUED OCTOBER 31, 2014 — DECIDED JANUARY 5, 2015


   Before POSNER, ROVNER, and HAMILTON, Circuit Judges.

    ROVNER, Circuit Judge. Carl Morris pled guilty to one count
of distribution of crack cocaine, in violation of 21 U.S.C.
§ 841(a)(1). Although the district court sentenced him below
the guidelines range, it did so without addressing his principal
arguments in mitigation. Because we cannot determine from
2                                                 No. 14-2242

this record whether the court considered those arguments in
fashioning the sentence, we vacate and remand for re-sentenc-
ing.
                                I.
    Morris was with a friend one day when that friend sold
crack cocaine to another man. Not knowing that the buyer was
a confidential informant, Morris then called the man and
offered to sell him crack cocaine. The informant initially
requested a quarter ounce of crack from Morris. On
December 3, 2012, Morris delivered less than half that amount
(3.288 grams) to the informant but charged him for the full
amount. The informant then ordered another quarter ounce
and asked to be reimbursed for the earlier shortage. On
December 5, 2012, Morris delivered slightly more than a
quarter ounce (7.447 grams) of crack to the informant. At the
direction of his police handlers, the informant then substan-
tially increased his order, asking for an ounce and a half of
crack cocaine. Morris agreed to the sale but on December 19,
2012, he delivered an ounce and a half (45 grams) of a counter-
feit substance that contained no crack cocaine in exchange for
$1900. Morris was charged in a two-count indictment with the
first two deliveries. He eventually pled guilty to the charge
related to the second delivery.
    A probation officer prepared a Presentence Investigation
Report (“PSR”) calculating the guidelines range applicable to
the offense conduct (the December 5 delivery) as well as
relevant conduct (the December 3 delivery and the uncharged
December 19 delivery of a counterfeit substance). See U.S.S.G.
§ 1B1.3 and Application Note 9. Under Application Note 4 of
No. 14-2242                                                      3

U.S.S.G. § 2D1.1, counterfeit substances are treated the same as
controlled substances when calculating the guidelines range,
and so the PSR held Morris accountable for 55.735 grams of
crack cocaine. Guidelines sentences for drug crimes are heavily
influenced by the quantity of drugs involved and so Morris’s
sentence was driven largely by the counterfeit substance,
which accounted for more than 80% of the drug weight.
Moreover, the guidelines tables penalize crack cocaine offenses
much more harshly than powder cocaine crimes, applying an
18:1 sentencing ratio. In Morris’s case, the PSR set forth a
guidelines range of 57 to 71 months of imprisonment.
    Morris filed a sentencing memorandum arguing first that
the government had engaged in sentencing entrapment by
directing the confidential informant to order a much greater
quantity of crack cocaine than Morris had previously sold. He
contended that the record contained no evidence that he had
a history of selling or an ability to sell such a large quantity of
drugs. That he never could have filled such a large order was
bolstered, he claimed, by his resort to delivering a counterfeit
substance that contained no crack cocaine at all.
    Morris next urged the court to apply a 1:1 crack-to-powder
cocaine ratio for his offense because the guidelines disparity
was the result of political compromise rather than for any
reason founded in medical, chemical, physiological, or other
scientific or social science evidence. If the court employed a 1:1
ratio, Morris calculated that his guidelines range would drop
to 21 to 27 months. Finally, Morris noted that, if the court
removed the counterfeit drugs from the equation, his advisory
sentencing range would be 15 to 21 months. In short, the
combination of a large quantity of counterfeit drugs, an
4                                                 No. 14-2242

amount that was ordered at the government’s direction,
together with the crack/powder sentencing disparity, dramati-
cally increased the advisory guidelines range from 15-to-21
months to 57-to-71 months. Morris argued that these factors
along with his recent efforts to rehabilitate himself warranted
a sentence of 18 months imprisonment.
   At the sentencing hearing, the government agreed that a
sentence within the 57-to-71 month advisory guidelines range
might not be appropriate but characterized the 18 month
request as “woefully inadequate.” The government noted that
Morris initiated contact with the informant and offered to sell
him crack, negating any inference that Morris was entrapped.
The government characterized Morris’s use of a counterfeit
substance as an attempt to “rip off” the informant rather than
evidence that Morris could not deliver the larger amount of
crack.
    The district court judge, who had previously sentenced
Morris at a probation revocation hearing, was well-versed with
his life story. The court noted and took into account Morris’s
difficult family history, his attempts at rehabilitation, his
failures at avoiding a return to crime, his attempts at employ-
ment and education, and other factors relevant under section
3553(a). But the court did not remark on his principal argu-
ments in mitigation, which were raised in both the sentencing
memorandum and at the sentencing hearing. Namely, the
court did not address his claim that the weight of the counter-
feit substance, combined with the crack/powder disparity
unfairly drove his sentencing range significantly higher. The
court ultimately decided on a below-guidelines sentence:
No. 14-2242                                                      5

     Taking into consideration the nature of the offense,
     as well as your personal history and characteristics,
     I’m persuaded that a custodial sentence of 48
     months is reasonable and no greater than necessary
     to hold you accountable, protect the community,
     provide you the opportunity for rehabilitative
     programs and achieve parity with the sentences of
     similarly-situated offenders.
R. 28, Sent. Tr. at 12. Morris appeals.
                                  II.
     On appeal, Morris contends that the district court commit-
ted procedural error when it failed to address his principal
arguments in mitigation. He asks that we vacate and remand
for resentencing. Our review of sentencing decisions generally
is limited to whether they are reasonable, applying the abuse
of discretion standard. Gall v. United States, 552 U.S. 38, 46
(2007). We first must ensure that the district court committed
no significant procedural error, including, among other things,
incorrectly calculating the guidelines range, or failing to
explain adequately the chosen sentence. Gall, 552 U.S. at 51. If
the district court erred in sentencing Morris, we will apply the
doctrine of harmless error in determining whether resen-
tencing is necessary. United States v. Olson, 450 F.3d 655, 683
(7th Cir. 2006). An error related to the validity of a defendant's
sentence is harmless only if it did not affect the district court's
choice of sentence. Olson, 450 F.3d at 683; United States v.
Schlifer, 403 F.3d 849, 854 (7th Cir. 2005).
   Before turning to the merits of Morris’s claim, we must
address the government’s claim that he waived any challenge
6                                                     No. 14-2242

to the adequacy of the district court’s treatment of his mitiga-
tion arguments. After imposing the sentence, the court asked,
“Anything further in this matter?” The government then
moved to dismiss the remaining count of the indictment and
the court granted that motion. The court then asked Morris’s
counsel if there was “anything further?” and she replied, “No,
Your Honor. Thank you.” The government cites our opinion in
Garcia-Segura for the proposition that counsel’s failure at that
point to ask for a specific ruling on the mitigation claims
operates as a waiver of those claims on appeal. See United States
v. Garcia-Segura, 717 F.3d 566 (7th Cir.), cert. denied, 134 S. Ct.
667 (2013). We disagree.
    In Garcia-Segura, we noted that it was not uncommon for a
defendant to argue on appeal that the district court had not
adequately addressed a principal argument in mitigation. We
therefore encouraged district courts to address the adequacy
of the review on the record:
     In order to ensure that defendants feel that they
     have had such arguments in mitigation addressed
     by the court and to aid appellate review, after
     imposing sentence but before advising the defen-
     dant of his right to appeal, we encourage sentencing
     courts to inquire of defense counsel whether they
     are satisfied that the court has addressed their main
     arguments in mitigation. If the response is in the
     affirmative, a later challenge for failure to address a
     principal mitigation argument under the reasoning
     of Cunningham would be considered waived. If not,
     the trial court would have the opportunity to clarify
     whether it determined that the argument was “so
No. 14-2242                                                      7

     weak as not to merit discussion,” lacked a factual
     basis, or has rejected the argument and provide a
     reason why. See Cunningham, 429 F.3d at 679. An
     affirmative answer, however, would not waive an
     argument as to the merits or reasonableness of the
     court's treatment of the issue.
Garcia-Segura, 717 F.3d at 569. In this case, the district court’s
generic inquiry of “anything further?” did not serve the
specific purpose we had in mind in Garcia-Segura. The point of
Garcia-Segura was to “make[] it possible to correct a genuine
Cunningham procedural error on the spot, at the end of the
sentencing hearing in the district court.” United States v.
Donelli, 747 F.3d 936, 941 (7th Cir. 2014). A general inquiry of
whether the parties have any further business before the court
is certainly useful; in this instance, the government used that
opportunity to move to dismiss the remaining count of the
indictment. But that blanket query did not alert Morris’s
counsel that she needed to do something further to preserve
her sentencing arguments, as we envisioned in Garcia-Segura.
We again encourage courts to ask defense counsel “whether
they are satisfied that the court has addressed their main
arguments in mitigation.” Garcia-Segura, 717 F.3d at 569. See
also Donelli, 747 F.3d at 940-41 (Cunningham procedural error
waived where the court asked whether counsel required
further elaboration of the court’s reasons for the sentence and
counsel replied in the negative). But there was no waiver here.
Morris’s lawyer did everything necessary to preserve the issue
for appeal. See Fed. R. Crim. P. 51; United States v. Bartlett, 567
F.3d 901, 910 (7th Cir. 2009) (noting that the rules do not
require a litigant to complain about a judicial choice after it has
8                                                     No. 14-2242

been made; rather, a litigant preserves a contention for review
by informing the court before the decision is made of the action
the party wishes the court to take and the grounds for that
action).
    We turn to the merits of Morris’s claim. Morris argued that
the court should reduce his guidelines sentence because the
informant’s police handlers directed the large size of the final
purchase, because most of the drug quantity attributed to him
was a counterfeit substance, and because he was subjected to
the 18:1 crack-to-powder cocaine ratio for that counterfeit
substance. In combination, these factors subjected him to a
significantly greater sentencing range, and yet the court did
not comment on these principal arguments in mitigation. A
judge need not comment on every argument the defendant
raises. United States v. Miranda, 505 F.3d 785, 792 (7th Cir. 2007).
“[A]rguments clearly without merit can, and for the sake of
judicial economy should, be passed over in silence.” United
States v. Cunningham, 429 F.3d 673, 678 (7th Cir. 2005). But
when a court gives little or no attention to the defendant's
principal argument when that argument “was not so weak as
not to merit discussion,” we cannot have confidence that the
judge adequately considered the section 3553(a) factors.
Cunningham, 429 F.3d at 679. “[I]f anyone acquainted with the
facts would have known without being told why the judge had
not accepted the argument,” then the judge need not specifi-
cally comment on that argument. Id. See also Garcia-Segura,
717 F.3d at 568 (a sentencing court must address a defendant's
principal arguments in mitigation unless they are too weak to
merit discussion); Miranda, 505 F.3d at 792 (same).
No. 14-2242                                                        9

   We have twice held that a defendant’s argument for a
reduced ratio between crack and powder cocaine offenses is
“not so weak as to not merit discussion.” United States v.
Johnson, 643 F.3d 545, 549 (7th Cir. 2011). See also United States v.
Arberry, 612 F.3d 898, 899 (7th Cir. 2010) (same). Indeed, the
Supreme Court indicated that district courts possessed the
discretion to conclude that the crack/powder sentencing ratio
was greater than necessary to achieve sentencing goals:
     The crack cocaine Guidelines … do not exemplify
     the Commission's exercise of its characteristic insti-
     tutional role. In formulating Guidelines ranges for
     crack cocaine offenses, as we earlier noted, the
     Commission looked to the mandatory minimum
     sentences set in the 1986 Act, and did not take
     account of “empirical data and national experience.”
     See Pruitt, 502 F.3d, at 1171 (McConnell, J., concur-
     ring). Indeed, the Commission itself has reported
     that the crack/powder disparity produces dispropor-
     tionately harsh sanctions, i.e., sentences for crack
     cocaine offenses “greater than necessary” in light of
     the purposes of sentencing set forth in § 3553(a). See
     supra, at 568. Given all this, it would not be an abuse
     of discretion for a district court to conclude when
     sentencing a particular defendant that the
     crack/powder disparity yields a sentence “greater
     than necessary” to achieve § 3553(a)'s purposes,
     even in a mine-run case.
Kimbrough v. United States, 552 U.S. 85, 109-10 (2007). See also
Spears v. United States, 555 U.S. 261, 265-66 (2009) (“we now
10                                                  No. 14-2242

clarify that district courts are entitled to reject and vary
categorically from the crack-cocaine Guidelines based on a
policy disagreement with those Guidelines.”). Moreover,
Morris’s circumstances did not present a “mine-run case”
because he was subjected to a substantially increased penalty
not for delivering crack cocaine but for delivering a counterfeit
substance.
    The government concedes that the district court failed to
address Morris’s argument that his sentence was unfairly
driven by the crack/powder disparity, by the inclusion of a
large amount of a counterfeit substance in the drug calculation,
and by the actions of the informant’s police handlers. Under
Johnson and Arberry, that was a procedural error. Although it
is true that the court granted Morris a below-guidelines
sentence, it is impossible to discern from this record whether
the court credited Morris’s principal arguments in fashioning
that sentence and so we must remand. Johnson, 643 F.3d at 549
(remand is necessary to consider the defendant’s argument
regarding the crack/powder disparity even when the court
sentenced the defendant below the guidelines range). The court
may well have considered and rejected Morris’s arguments
and simply neglected to memorialize that analysis on the
record. Perhaps the court concluded, for example, that deliver-
ing a counterfeit substance presented the same risk for violence
as delivering crack cocaine. We offer no opinion on the
reasonableness of Morris’s below-guidelines sentence should
the district court decide to reimpose it. But because we cannot
No. 14-2242                                                11

determine whether the error here affected the district court's
choice of sentence, it may not be characterized as harmless.
Olson, 450 F.3d at 683; Schlifer, 403 F.3d at 854.
                              VACATED AND REMANDED.
