     05-5739-cr
     United States v. Regalado


 1
 2                      UNITED STATES COURT OF APPEALS
 3
 4                           FOR THE SECOND CIRCUIT
 5
 6                                 August Term, 2007
 7
 8
 9   (Argued: December 11, 2007                    Decided: March 4, 2008
10
11                                                     Amended: May 9, 2008)
12
13                               Docket No. 05-5739-cr
14
15   - - - - - - - - - - - - - - - - - - - -X

16   UNITED STATES OF AMERICA,

17               Appellee,

18               -v.-

19   JOSE REGALADO,

20               Defendant-Appellant.

21   - - - - - - - - - - - - - - - - - - - -X

22         Before:           JACOBS, Chief Judge, POOLER and SACK,
23                           Circuit Judges.
24
25
26         Appeal from the sentence of the United States District

27   Court for the Southern District of New York (Leisure, J.),

28   following defendant’s guilty plea to conspiring to

29   distribute and possess with intent to distribute cocaine

30   base.    In light of Kimbrough v. United States, --- U.S. ---,

31   128 S. Ct. 558 (2007), we are unable to discern whether the
1    district court would have imposed a non-Guidelines sentence

2    had it been aware that “the cocaine Guidelines, like all

3    other Guidelines, are advisory only,” and that it therefore

4    had discretion to deviate from the Guidelines where

5    necessary to serve the objectives of sentencing under 18

6    U.S.C. § 3553(a).   Id. at 564, 575.   Without that

7    information, we cannot say whether there was plain error.

8    Accordingly, the case is remanded for further proceedings

9    consistent with this opinion.

10
11                               B. Alan Seidler, New York, NY,
12                               for Defendant-Appellant.
13
14                               Stephen A. Miller, Assistant
15                               United States Attorney (Michael
16                               J. Garcia, United States
17                               Attorney, Southern District of
18                               New York, on the brief, Daniel
19                               A. Braun, Assistant United
20                               States Attorney, of counsel),
21                               United States Attorney’s Office
22                               for the Southern District of New
23                               York, New York, NY, for
24                               Appellee.
25
26   PER CURIAM1
27
28       Jose Regalado appeals from the sentence of 262 months’

29   imprisonment imposed by the United States District Court for


         1
          After due consideration of the government’s petition
     for rehearing, which is denied, we have sua sponte amended
     our opinion.
                                     2
1    the Southern District of New York (Leisure, J.), following

2    his May 1, 2003 guilty plea to conspiring to distribute and

3    possess with intent to distribute cocaine base.     In light of

4    Kimbrough v. United States, --- U.S. ---, 128 S. Ct. 558

5    (2007), we are unable to discern whether the district court

6    would have imposed a non-Guidelines sentence had it been

7    aware that “the cocaine Guidelines, like all other

8    Guidelines, are advisory only,” and that it therefore had

9    discretion to deviate from the Guidelines where necessary to

10   serve the objectives of sentencing under 18 U.S.C. §

11   3553(a).   Id. at 564, 575.   We remand the case to the

12   district court for further proceedings necessary to

13   determine whether resentencing is required. 2

14

15                            BACKGROUND

16       Regalado pleaded guilty to conspiring to distribute and

17   possess with intent to distribute cocaine base in violation

18   of 21 U.S.C. §§ 841(a)(1) and 841(b)(1)(A).     At sentencing,

19   the district court determined that Regalado distributed more

20   than 1.5 kilograms of cocaine base, which resulted in a base


         2
          Prior to filing, this opinion has been circulated to
     all members of this Court. See, e.g., United States v.
     Crosby, 397 F.3d 103, 105 n.1 (2d Cir. 2005).
                                    3
1    offense level of 38.     See U.S.S.G. § 2D1.1(c)(1) (2004).

2    After a four-level enhancement for Regalado’s leadership

3    role, see § 3B1.1(a), and a three-level reduction for

4    acceptance of responsibility, see § 3E1.1(a) and (b), the

5    resulting sentencing range (at criminal history category I)

6    was 262-327 months.     Regalado unsuccessfully sought a

7    downward departure based on extraordinary family

8    circumstances.   However, he did not ask the district court

9    to deviate from the Guidelines on the ground that the base

10   offense levels for crack cocaine fail to serve the

11   objectives of sentencing under § 3553(a).     Judge Leisure

12   sentenced Regalado principally to a term of 262 months’

13   imprisonment, the bottom of the Guidelines range.

14       Regalado appealed, and we remanded the case for further

15   proceedings pursuant to United States v. Crosby, 397 F.3d

16   103 (2d Cir. 2005).     On remand, the government argued that

17   the original Guidelines sentence was reasonable and should

18   not be disturbed.     Regalado’s Crosby submission requested

19   leniency, but made no argument bearing on the district

20   court’s discretion to deviate from the sentencing ranges for

21   crack cocaine offenses.     The district court reviewed its

22   original Guidelines calculation, gave renewed consideration


                                     4
1    to the 18 U.S.C. § 3553(a) factors, and discussed and

2    responded to the parties’ Crosby submissions.         It then

3    concluded that it would not have imposed a non-trivially

4    different sentence had the Guidelines been advisory rather

5    than mandatory.   It therefore declined to resentence

6    Regalado, and this appeal followed.

7

8                              DISCUSSION

9                                    I

10       The Guidelines’ drug quantity table sets base offense

11   levels for crack and powder cocaine offenses.         See U.S.S.G §

12   2D1.1.   In Kimbrough v. United States, --- U.S. ----, 128 S.

13   Ct. 558 (2007), the Supreme Court held that “the cocaine

14   Guidelines, like all other Guidelines, are advisory only.”

15   Id. at 564.   Although a sentencing judge must “give

16   respectful consideration to the Guidelines” among “the array

17   of factors warranting consideration,” the judge also has

18   discretion to determine that “in the particular case, a

19   within-Guidelines sentence is ‘greater than necessary’ to

20   serve the objectives of sentencing.”       Id. at 564, 570

21   (citing 18 U.S.C. § 3553(a)).       “In making that

22   determination, the judge may consider the disparity between


                                     5
1    the Guidelines’ treatment of crack and powder cocaine

2    offenses,” so long as the court does not “purport to

3    establish a ratio of its own.”     Kimbrough, 128 S. Ct. at

4    564, 575.    Kimbrough thus emphasized the broad discretion of

5    a district court “‘to tailor [a] sentence in light of other

6    statutory concerns.’”    Id. at 570 (quoting United States v.

7    Booker, 543 U.S. 220, 245-46 (2005)).

8        In our review, we owe deference to that discretion.

9    Kimbrough, 128 S. Ct. at 576 (“The ultimate question in

10   Kimbrough’s case is . . . ‘whether the District Judge abused

11   his discretion in determining that the § 3553(a) factors

12   supported a sentence of [15 years] and justified a

13   substantial deviation from the Guidelines range.’”) (quoting

14   Gall v. United States, --- U.S. ----, 128 S. Ct. 586, 600

15   (2007) (alteration in original)).     As the Supreme Court

16   recently explained in Gall v. United States, “the appellate

17   court must review the sentence under an abuse-of-discretion

18   standard.”   128 S. Ct. at 597.    First, we “ensure that the

19   district court committed no significant procedural error,”

20   such as “treating the Guidelines as mandatory . . . .”        Id.

21   Next, we review the substantive reasonableness of the

22   sentence for abuse of discretion.     Id.   Such review should


                                    6
1    “take into account the totality of the circumstances,

2    including the extent of any variance from the Guidelines

3    range. . . . It may consider the extent of the deviation,

4    but must give due deference to the district court’s decision

5    that the § 3553(a) factors, on a whole, justify the extent

6    of the variance.”     Id.   Furthermore, we may not reverse the

7    district court simply because we would have imposed a

8    different sentence.     Id.

9        This guidance and direction from the Supreme Court

10   confirms the broad deference that this Circuit has afforded

11   the sentencing discretion of the district courts.     See,

12   e.g., United States v. Fernandez, 443 F.3d 19, 27 (2d Cir.

13   2006); United States v. Crosby, 397 F.3d 103, 112-14 (2d

14   Cir. 2005); United States v. Fleming, 397 F.3d 95, 100 (2d

15   Cir. 2005).   However, until Kimbrough and Gall, this Circuit

16   tended to discourage district courts from deviating from the

17   crack cocaine Guidelines.     Our opinion in United States v.

18   Castillo, 460 F.3d 337 (2d Cir. 2006), may have been over-

19   read or misread to inhibit any deviation.      District courts

20   may also have been inhibited from exercising their full

21   discretion by the fact that the Sentencing Commission

22   borrowed the 100-to-1 Guidelines ratio from the mandatory


                                      7
1    minimums for drug offenses decreed by Congress.   Id. at 567

2    (explaining origin of Guidelines crack to powder ratio).

3    Therefore, when a district court sentenced a defendant for a

4    crack cocaine offense before Kimbrough, there was an

5    unacceptable likelihood of error; certainly, the court acted

6    under the influence of a widespread assumption that is now

7    known to be erroneous.   Where the defendant failed to argue

8    for such a deviation from the Guidelines range before the

9    sentencing court, it is impossible to know, ex post, whether

10   the court would have exercised its discretion to mitigate

11   the sentencing range produced by the 100-to-1 disparity.

12       In this situation, we review for plain error.   “To

13   demonstrate plain error, a defendant must show (1) error,

14   (2) that is plain at the time of appellate review, and (3)

15   that affects substantial rights.   Where these conditions are

16   met, we have the discretion to notice a forfeited error if

17   (4) it seriously affects the fairness, integrity, or public

18   reputation of judicial proceedings.”   United States v.

19   Quinones, 511 F.3d 289, 316 (2d Cir. 2007) (citing United

20   States v. Olano, 507 U.S. 725, 732 (1993); United States v.

21   Rybicki, 354 F.3d 124, 129 (2d Cir. 2003) (en banc); United

22   States v. Thomas, 274 F.3d 655, 667 (2d Cir. 2001) (en


                                   8
1    banc)).   Since the district court was, quite understandably,

2    unaware of (or at least insecure as to) its discretion to

3    consider that the 100-to-1 ratio might result in a sentence

4    greater than necessary, there was an unacceptable likelihood

5    of error.   While the risk of such error in crack sentences

6    imposed between Booker and Castillo is not so high as to

7    invariably satisfy the first step of plain error analysis,

8    it is sufficiently real to merit identification in

9    individual cases.   As we have held, “in the sentencing

10   context there are circumstances that permit us to relax the

11   otherwise rigorous standards of plain error review to

12   correct sentencing errors.”     United States v. Sofsky, 287

13   F.3d 122, 125 (2d Cir. 2002).       Such relaxation is

14   appropriate here because a sizable portion of post-Booker,

15   pre-Castillo cases where error is identified will also

16   satisfy the third and fourth plain error factors given the

17   judiciary’s long-standing concerns about the severity of the

18   crack Guidelines.   See, e.g., United States v. Moore, 54

19   F.3d 92, 99, 102 (2d Cir. 1995) (rejecting equal protection

20   challenge to crack Guidelines but commenting that “[t]he

21   statistical evidence of disparate impact and several

22   questionable passages in the legislative record are


                                     9
1    discomfiting” and that “Moore’s arguments raise troublesome

2    questions about the fairness of the crack cocaine sentencing

3    policy”); United States v. Singleterry, 29 F.3d 733, 741

4    (1st Cir. 1994) (“Although Singleterry has not established a

5    constitutional violation, he has raised important questions

6    about the efficacy and fairness of our current sentencing

7    policies for offenses involving cocaine substances.”).     The

8    unusual circumstances surrounding application of the crack

9    Guidelines in the Circuit after Booker and before Castillo

10   justify a narrow and limited exception to our general rule

11   that sentencing courts are presumed to know and follow the

12   applicable sentencing law.   See United States v. Fernandez,

13   443 F.3d 19, 30 (2d Cir. 2006); United States v. Gonzalez,

14   281 F.3d 38, 42 (2d Cir. 2002).

15       If the district court did not fully appreciate the

16   extent of its discretion to deviate from the crack

17   Guidelines range prior to Kimbrough, there was an error.

18   After Kimbrough, such error would be plain.   The remaining

19   questions are whether the likely error affects substantial

20   rights and whether the error seriously affects the fairness,

21   integrity or public reputation of judicial proceedings.    We

22   cannot address those issues on the present record.


                                   10
1                                   II

2        In United States v. Crosby we confronted an analogous

3    situation.    There, the likely error was that prior to United

4    States v. Booker, 543 U.S. 220 (2005), a district court

5    understood the Guidelines to be mandatory.        See Crosby, 397

6    F.3d at 115-16.     However, the defendant failed to object to

7    the mandatory application of the Guidelines below, and so we

8    reviewed for plain error.    Id. at 116.   We assumed that the

9    district court was influenced by the widespread assumption

10   that the Guidelines were mandatory, which was error, and we

11   saw after Booker that the error was plain.        However, we

12   could not tell whether the error affected a substantial

13   right because we could not tell on appeal whether the

14   district court would have imposed a non-trivially different

15   sentence had it recognized that the Guidelines were

16   advisory.     Accordingly, we ruled that “pre-Booker/Fanfan

17   sentences pending on direct review [require] remand to the

18   district court, not for the purpose of a required

19   resentencing, but only for the more limited purpose of

20   permitting the sentencing judge to determine whether to

21   resentence, now fully informed of the new sentencing

22   regime.”     Id. at 117 (emphasis in original).    Thus, on a


                                     11
1    Crosby remand, the district court must indicate whether, at

2    the time of the original sentence, it would have imposed a

3    non-trivially different sentence under advisory Guidelines.

4    Id. at 118.   If so, vacatur and resentencing is required.

5    Id. at 120.   If not, the district court must “place on the

6    record a decision not to resentence, with an appropriate

7    explanation,” id., and we will then review the sentence for

8    reasonableness.   United States v. Williams, 475 F.3d 468,

9    474 (2d Cir. 2007).

10       Similarly, when the sentencing of a defendant for a

11   crack cocaine offense occurred before Kimbrough, we cannot

12   tell whether the district court would have exercised its now

13   clear discretion to mitigate the sentencing range produced

14   by the 100-to-1 ratio.   If it would have, an affirmance of

15   the original sentence would “seriously affect[] the

16   fairness, integrity, or public reputation of judicial

17   proceedings,” Quinones, 511 F.3d at 316, because imposition

18   of a sentence that the district court would not have imposed

19   had it fully appreciated the extent of its discretion would,

20   in our view, “seriously undermine the public’s confidence in

21   the judicial process.”   United States v. Keigue, 318 F.3d

22   437, 445 (2d Cir. 2003) (discussing district court’s


                                   12
1    erroneous use of expired version of the Guidelines).     “This

2    is especially true given the relative ease of correcting the

3    sentencing error on remand, thus accentuating the potential

4    unfairness of allowing the district court’s error to stand.”

5    United States v. Gordon, 291 F.3d 181, 195 (2d Cir. 2002).

6        We therefore adopt the Crosby mechanism and apply it

7    here.   Where a defendant has not preserved the argument that

8    the sentencing range for the crack cocaine offense fails to

9    serve the objectives of sentencing under § 3553(a), we will

10   remand to give the district court an opportunity to indicate

11   whether it would have imposed a non-Guidelines sentence

12   knowing that it had discretion to deviate from the

13   Guidelines to serve those objectives.   If so, the court

14   should vacate the original sentence and resentence the

15   defendant.   If not, the court should state on the record

16   that it is declining to resentence, and it should provide an

17   appropriate explanation for this decision.   On appeal, if we

18   have not already done so, we will review the sentence for

19   reasonableness.

20       Crosby recognized that a resentencing might yield a

21   higher sentence.   That is a remote and (at most) rare

22   prospect on a remand under Kimbrough.   Nevertheless, (as in


                                   13
1    Crosby) the “remand, on a defendant’s appeal, that

2    authorizes a district judge to consider whether to

3    resentence and that permits resentencing should include an

4    opportunity for a defendant to avoid resentencing by

5    promptly notifying the district judge that resentencing will

6    not be sought.”    Crosby, 397 F.3d at 118.   Likewise, we

7    “intimate no view at this time as to whether the Ex Post

8    Facto Clause would prohibit a court from imposing a more

9    severe sentence than a defendant would have received had the

10   [cocaine] Guidelines [been considered] mandatory.”     Id. at

11   117 n.17 (citing United States v. Broderson, 67 F.3d 452,

12   456 (2d Cir. 1995)).

13

14                                 III

15        Regalado’s brief on appeal, filed pre-Kimbrough, does

16   not contest the 100-to-1 ratio.     (The arguments Regalado did

17   raise on appeal would ordinarily have been considered and

18   decided in a summary order, on the grounds set forth in the

19   margin.3 )   Because Regalado does not raise this argument on


          3
          Regalado   argues that his sentence was substantively
     unreasonable,   but we owe deference to the district court’s
     evaluation of   his personal circumstances, United States v.
     Gallante, 111   F.3d 1029, 1034 (2d Cir. 1997), and cannot
     conclude that   his sentence “exceed[s] the bounds of
                                    14
1   appeal, we would ordinarily treat it as forfeited.     United

2   States v. Pereira, 465 F.3d 515, 520 n.5 (2d Cir. 2006).        We

3   are not required to do so, however.     Sniado v. Bank Austria

4   AG, 378 F.3d 210, 213 (2d Cir. 2004).    On the circumstances

5   presented by this appeal, we think it the better course to

6   consider the argument.

7       We cannot know whether the district court would have

8   imposed a non-Guidelines sentence had it been aware (or

9   fully aware) of its discretion to deviate from the crack




    allowable discretion.” United States v. Fernandez, 443 F.3d
    19, 27 (2d Cir. 2006) (citation and internal quotation marks
    omitted). We also reject Regalado’s Sixth Amendment claim
    that his offense level was calculated based on a drug
    quantity determined by the district court because during his
    plea allocution he admitted to distributing more than 1.5
    kilograms of crack cocaine, more than the 50 grams necessary
    to trigger a ten-year mandatory minimum sentence under 21
    U.S.C. § 841(b)(1)(A). In addition, Regalado’s
    (unpreserved) due process challenge to the 100-to-1 powder
    to crack cocaine ratio underlying his sentence is without
    merit as we have repeatedly rejected similar constitutional
    challenges. See, e.g., United States v. Stevens, 19 F.3d
    93, 97 (2d Cir. 1994). As for Regalado’s ineffective
    assistance of counsel claim, he argues only that his trial
    attorney failed to raise the above constitutional challenges
    to his sentence, but “[f]ailure to make a meritless argument
    does not amount to ineffective assistance.” United States
    v. Arena, 180 F.3d 380, 396 (2d Cir. 1999). It is therefore
    “beyond any doubt” that his attorney’s assistance was not
    ineffective. United States v. Matos, 905 F.2d 30, 32 (2d
    Cir. 1990).


                                 15
1    cocaine ranges in light of the objectives of sentencing.4

2    Because we are unable to tell whether the likely procedural

3    error (i.e., unawareness of discretion to consider that the

4    100-to-1 ratio may cause a particular sentence to be

5    excessive) affected substantial rights and affected the

6    fairness, integrity or public reputation of judicial

7    proceedings, we must remand.5

8

9                                    IV

10       After additional research and experience with the

11   Guidelines, the Sentencing Commission concluded that the



         4
          This appeal presents an additional wrinkle because on
     a Crosby remand–-where the issue is whether the sentencing
     judge would have imposed a non-trivially different sentence
     had it anticipated Booker--there would have been no occasion
     for the Court to consider the harshness of the 100-to-1
     ratio. Even if the court did consider this issue, it would
     not have had to say so explicitly. However, where, as here,
     a district court declines to resentence on a Crosby remand,
     we still review the underlying sentence for reasonableness.
     United States v. Williams, 475 F.3d 468, 474 (2d Cir. 2007).
     Therefore, we must assess whether the original sentencing
     was infected by procedural error. Id.
         5
          Should Regalado appeal from the district court’s
     decision on remand, “the law of the case doctrine ordinarily
     will bar [him] from renewing challenges to rulings made by
     the sentencing court that were adjudicated by this Court–-or
     that could have been adjudicated by us had [Regalado] made
     them–-during the initial appeal” that led to a remand.
     Williams, 475 F.3d at 475.
                                     16
1    100-to-1 powder to crack ratio fails to meet the objectives

2    of sentencing because it rests on unsupported assumptions

3    about the relative harmfulness of the drugs, it punishes

4    “retail” crack dealers more harshly than “wholesale” drug

5    distributors, and it promotes an unwarranted disparity based

6    on race.    Kimbrough, 128 S. Ct. at 568 (citing United States

7    Sentencing Commission, Report to Congress: Cocaine and

8    Federal Sentencing Policy 91-103 (May 2002)).     Repeated

9    efforts by the Commission to reduce the crack to powder

10   ratio beginning in 1995 failed to induce congressional

11   action.    Kimbrough, 128 S. Ct. at 569.

12       However, the Commission recently reduced the base

13   offense level associated with each quantity of crack by two

14   levels, effective November 1, 2007.    See U.S.S.G. § 2D1.1

15   (2007); Amendments to the Sentencing Guidelines for United

16   States Courts, 72 Fed. Reg. 28571-28572 (2007).    That change

17   has been given retroactive effect because the Sentencing

18   Commission added this amendment to those listed at U.S.S.G.

19   § 1B1.10(c).   See United States v. Garcia, 339 F.3d 116, 120

20   (2d Cir. 2003).   Therefore, the district courts now have

21   jurisdiction pursuant to 18 U.S.C. § 3582(c)(2) to decide in

22   the first instance whether to modify previously-imposed


                                    17
1    sentences where the cocaine ranges on which they were based

2    have subsequently been lowered.    To invoke the district

3    courts’ jurisdiction, defendants should move for

4    modification of their sentences pursuant to 18 U.S.C. §

5    3582(c)(2) in the district courts.    (Assistance under the

6    Criminal Justice Act can be expected to be available for

7    such motions.)   In deciding whether to modify the sentence,

8    district courts must consider the factors set forth in 18

9    U.S.C. § 3553(a) anew and in light of Gall and Kimbrough to

10   the extent that they may be applicable, and relevant

11   Sentencing Commission policy statements.    See 18 U.S.C. §

12   3582(c)(2).

13       In considering the present appeal, we recognize that

14   whether we remand now or consign Regalado to seeking relief

15   by motion, the ultimate result may well be the same.      There

16   are certain factual equivalencies between deciding whether

17   one would have imposed a non-Guidelines sentence with

18   broader discretion to deviate from the Guidelines, and

19   arriving at a different sentence by a different Guidelines

20   computation entirely (which might obviate the need to

21   exercise that discretion).   At the same time, it makes

22   little sense to allow a judgment to become final even though



                                   18
1   the district court would not have imposed it in light of its

2   now better defined powers so that the same essential

3   question can be presented by motion.   Therefore, the best

4   course is to remand to the district court.

5

6                            CONCLUSION

7       The case is remanded for further proceedings consistent

8   with this opinion.




                                 19
