                                                                         FILED
                                                             United States Court of Appeals
                                                                     Tenth Circuit

                                                                     July 29, 2008
                                                                 Elisabeth A. Shumaker
                     UNITED STATES COURT OF APPEALS                  Clerk of Court

                                   TENTH CIRCUIT


 UNITED STATES OF AMERICA,

          Plaintiff-Appellee,
                                                        No. 07-2018
 v.                                             (D.C. No. CR-05-1599 MCA)
                                                          (D.N.M.)
 ANTHONY DEWAYNE HASSON,

          Defendant-Appellant.


                                ORDER AND JUDGMENT *


Before LUCERO, TYMKOVICH, and GORSUCH, Circuit Judges.


      Anthony Dewayne Hasson appeals his conviction on one count of

conspiracy to distribute controlled substances and one count of conspiracy to

launder money, as well as his resulting sentence of 292 months’ imprisonment.

As to his convictions, Hasson urges that the district court erred in refusing to

allow him to withdraw his guilty plea and that he received constitutionally

deficient representation in entering the plea. With respect to his sentence, he



      *
        This order and judgment is not binding precedent, except under the
doctrines of law of the case, res judicata, and collateral estoppel. This court
generally disfavors the citation of orders and judgments; nevertheless, an order
and judgment may be cited under the terms and conditions of 10th Cir. R. 32.1.
maintains that the district court miscalculated his sentencing range by adding a

relevant specific offense characteristic to his base offense level after, rather than

before, grouping his separate counts of conviction.

      Because we conclude that the district court did not abuse its discretion in

refusing to allow Hasson to withdraw his plea and that his claim of ineffective

assistance of counsel is not properly pursued on direct appeal, we affirm his

convictions. We reverse and remand his sentence, however, because the district

court miscalculated Hasson’s sentencing range by grouping the distinct counts of

conviction before applying a specific offense characteristic relating to only one of

the counts, in contravention of U.S.S.G. § 1B1.1. Our jurisdiction arises under 28

U.S.C. § 1291 and 18 U.S.C. § 3742.

                                           I

      On July 26, 2005, Hasson, along with six codefendants, was indicted by a

grand jury in New Mexico on charges that he: (1) conspired to distribute more

than 1000 kilograms of marijuana and more than 5 kilograms of cocaine, in

violation of 21 U.S.C. §§ 841(a)(1), (b)(1)(A), and 846 (“Count 1”); (2) engaged

in a continuing criminal enterprise, in violation of 21 U.S.C. § 848(a), (c), and 18

U.S.C. § 2 (“Count 2”); and (3) conspired to launder money, in violation of 18

U.S.C. §§ 1956(a)(1)(A)(i), (a)(1)(B)(i), (h), and 1957 (“Count 3”). 1 Although he

      1
       Given the number of defendants and the 20,000 to 30,000 pages of
expected discovery, the district court designated this case as complex pursuant to
18 U.S.C. § 3161(h)(8)(B)(ii).

                                          -2-
initially pleaded not guilty to the charges, Hasson later entered into a plea

agreement with the government, in which he consented to plead guilty to Counts 1

and 3 in exchange for the government’s agreement to dismiss Count 2. 2

      The signed plea agreement contained several nonbinding stipulations

between the parties regarding the sentence calculation, three of which are relevant

to this appeal. First, the base offense level calculation under the United States

Sentencing Guidelines (“Guidelines”) for Count 1 would be set at 34, because of

Hasson’s “involvement in, or awareness of, the distribution of between 3,000 and

10,000 kilograms of marijuana.” See U.S.S.G. §§ 1B1.3, 2D1.1 (2005). Second,

the base offense level for Count 3 would be set at 32, based on Hasson’s

“laundering of the proceeds of between 1,000 and 3,000 kilograms of marijuana.”

See §§ 1B1.3, 2S1.1(a), 2D1.1(c). Finally, the parties agreed that Hasson “has

clearly demonstrated an affirmative acceptance of personal responsibility for [his]

criminal conduct,” and that he therefore would receive a three-level reduction in

the total offense level. See § 3E1.1. On August 23, 2006, Hasson went before

the district court and changed his plea to guilty in accordance with the terms of




      2
        Although Count 1 of the indictment alleged that Hasson had intentionally
conspired to distribute both cocaine and marijuana, Hasson pleaded guilty only to
conspiring to distribute marijuana.

                                          -3-
the plea agreement. The court accepted the plea and set the case over for

sentencing. 3

      Hasson’s Presentence Investigation Report (“PSR”) grouped the two counts

of conviction together under § 3D1.2(d), which requires that multiple counts be

grouped together when the offense behavior is ongoing or continuous in nature.

Relying on the stipulations in the plea agreement, the PSR then set the base

offense level for the combined counts at 34, the greater of the two base offense

levels. After grouping the counts, the PSR added two levels under

§ 2S1.1(b)(2)(B) because Hasson was convicted of violating 18 U.S.C. § 1956(h)

and four levels under U.S.S.G. § 3B1.1(a) because Hasson was alleged to have

been an organizer or leader of criminal activity that involved five or more

participants or that was otherwise extensive. Following a three-level deduction

for acceptance of responsibility, see § 3E1.1, the PSR calculated a total offense

level of 37. Taking this offense level together with Hasson’s criminal history

category of IV, the PSR yielded an advisory sentencing range of 292 to 365


      3
          In accepting Hasson’s guilty plea, the court stated:

      It is the finding of this Court . . . that this defendant is fully
      competent and capable of entering an informed plea to each of two
      counts, 1 and 3, he is aware of the nature and consequences of his
      pleas, and the pleas to Counts 1 and 3 of the indictment are
      knowing[] and voluntary pleas supported by a basis in fact containing
      each of the essential elements of the offense. I accept your pleas of
      guilty as to Counts 1 and 3, and I adjudicate you guilty of those
      offenses.

                                           -4-
months’ imprisonment for Count 1, and 240 months’ imprisonment—the statutory

maximum under 18 U.S.C. § 1956(h)—for Count 3.

       On December 11, 2006, approximately four months after the district court

accepted Hasson’s plea and only four days before his scheduled sentencing

hearing, Hasson moved to withdraw his guilty plea. He claimed that he did not

understand the consequences of his decision to plead guilty at the time he entered

his plea and that his plea was therefore not knowingly or voluntarily given.

Specifically, he maintained that although he had pleaded to participating in a

conspiracy, he had not admitted to being a leader, supervisor, manager, or

organizer of the conspiracy. Hasson also noted that the plea negotiations between

his counsel and the government contemplated a sentencing range “between 11 and

15 years,” and that the government never indicated that it would seek the

adjustments discussed in the PSR. He posited that “the government [was] seeking

to get through the sentencing process what was not negotiated in the plea

process.” 4

       At Hasson’s sentencing hearing on December 15, 2006, the district court

entertained argument on the motion to withdraw the plea. Weighing the factors

for determining whether to allow a defendant to withdraw a guilty plea, see, e.g.,

United States v. Yazzie, 407 F.3d 1139, 1142 (10th Cir. 2005), the district court

       4
       Prior to filing his motion to withdraw the guilty plea, Hasson also
challenged the sentencing adjustments noted in the PSR in a written sentencing
memorandum.

                                         -5-
found that Hasson had not made the requisite showing. It thus denied his motion

and proceeded to sentencing.

      As to the specifics of the PSR, Hasson objected to the manner in which the

two-level adjustment under U.S.S.G. § 2S1.1(b)(2)(B) was applied. He urged that

the adjustment should have been added to the original base offense level for

Count 3 only, rather than to the grouped counts, thereby yielding an adjusted base

offense level of 34, instead of 36. Hasson also challenged the leadership

adjustment under § 3B1.1(a), alleging that there was insufficient evidence in the

PSR to justify the adjustment and that without more detailed allegations regarding

the other criminal participants, he could not effectively argue against the

proposed adjustment.

      The court found that the two-level adjustment for money laundering was

properly applied. It was troubled, however, by the evidentiary basis for the

leadership adjustment, and ordered further briefing on the matter. Sentencing was

recessed until January 16, 2007.

      At the reconvened hearing, the district court found that the evidence

supported application of the leadership adjustment, and it adopted the PSR’s

calculations. As to Count 1, the court imposed a sentence of 292 months’

imprisonment, the bottom of the applicable Guidelines range, and a concurrent

240 months’ imprisonment for Count 3. Hasson now appeals from the judgment

and sentence entered against him.

                                         -6-
                                          II

      We begin with Hasson’s claim that the district court erred in denying his

motion to withdraw his guilty plea. He advances a two-fold argument. First, he

asserts that his trial counsel was constitutionally ineffective in failing to properly

advise him of the potential sentencing consequences of the plea agreement and

that he should have been able to withdraw his plea as a result of counsel’s

ineffectiveness. Second, he maintains that the district court abused its discretion

in denying his motion to withdraw his guilty plea because the relevant factors

favor withdrawal. Because the first argument is not properly pursued on direct

appeal, we dismiss it. We reject the second contention on the merits.

                                          A

      In contesting the district court’s denial of his motion to withdraw, Hasson

insists that his two trial attorneys were constitutionally ineffective in counseling

him with respect to the proposed plea agreement. Specifically, he claims that

because his attorneys failed to properly advise him of his potential sentencing

range, he must be allowed to withdraw the guilty plea. 5

      A plea agreement is not enforceable if it is the product of ineffective

assistance of counsel. See United States v. Edgar, 348 F.3d 867, 869 (10th Cir.

2003). But, except in rare circumstances, claims of ineffective assistance of


      5
         Hasson is not represented by the same counsel on appeal as he was in the
district court.

                                          -7-
counsel must be presented in collateral proceedings. United States v. Galloway,

56 F.3d 1239, 1240 (10th Cir. 1995) (en banc). When such claims are pursued on

direct appeal, they “are presumptively dismissible, and virtually all will be

dismissed.” Id. By encouraging collateral proceedings, this rule allows the

district court to develop the factual record and to reach an initial decision on the

merits of the claim. See Massaro v. United States, 538 U.S. 500, 505-06 (2003).

It also ensures that we have an adequate appellate record upon which to base our

decision. Galloway, 56 F.3d at 1240.

      We have, of course, permitted exceptions to this general rule, but only

where the factual record on ineffectiveness is fully developed. See, e.g., United

States v. Hamilton, 510 F.3d 1209, 1213 (10th Cir. 2007) (holding than an

ineffectiveness claim was reviewable on direct appeal where the district court

“held a lengthy hearing on the matter” and a “factual record enabling appellate

review already exist[ed]”); United States v. Carr, 80 F.3d 413, 416 n.3 (10th Cir.

1996) (reviewing a claim of ineffective assistance of counsel on direct appeal

where “[t]he district court held a lengthy hearing on the issue and then made a

specific finding that defendant’s counsel provided effective assistance”). In other

words, unless the record sufficiently describes the advice given by defendant’s

counsel concerning the plea decision, we must dismiss the Sixth Amendment

claim and leave it for consideration on collateral review. United States v. Carver,

160 F.3d 1266, 1268 (10th Cir. 1998).

                                          -8-
      Our review of the record here demonstrates that Hasson’s claim does not

fall within the narrow category of claims that require no further development.

Because Hasson did not assert this argument below, the district court never had an

opportunity to consider the ineffectiveness question, much less develop a record

on the issue. This case thus stands in stark contrast to cases such as Hamilton and

Carr, where we considered the claim of ineffectiveness on direct appeal. In

Hamilton, the district court convened “a lengthy hearing” to weigh the

ineffectiveness question and its effect on the defendant’s decision to plea

guilty—all before the case arrived in this court on direct appeal. 510 F.3d at

1213. Likewise, in Carr, the district court received testimony from the

defendant’s prior counsel and had the first cut at considering whether that

testimony showed ineffective assistance. 80 F.3d at 418. In this case, by

contrast, the district was never apprised of any concerns about Hasson’s

representation with respect to the plea agreement. As a result, the sum total of

record evidence we have on this question is Hasson’s trial attorneys’ statement in

the motion to withdraw the guilty plea that counsel “understood that the

sentencing range for [Hasson] would be between 11 and 15 years if [he] pled as

suggested in the plea agreement.” That allegation, standing alone, is insufficient

to enable meaningful appellate review of his claim. Consequently, we dismiss

this claim on direct appeal. Should Hasson intend to pursue the issue further, he

must raise it in a collateral proceeding pursuant to 28 U.S.C. § 2255.

                                         -9-
                                         B

      We turn to Hasson’s claim that the district court abused its discretion in

denying his motion to withdraw his guilty plea. Under Federal Rule of Criminal

Procedure 11(d)(2)(B), a defendant may withdraw a guilty plea before the district

court imposes sentence if he can “show a fair and just reason for requesting the

withdrawal.” In evaluating whether such a justification exists, a district court

must consider:

      (1) whether the defendant has asserted his innocence; (2) whether the
      government will be prejudiced if the motion is granted; (3) whether
      the defendant has delayed in filing the motion; (4) the inconvenience
      to the court if the motion is granted; (5) the quality of the
      defendant’s assistance of counsel; (6) whether the plea was knowing
      and voluntary; [and] (7) whether the granting of the motion would
      cause a waste of judicial resources.

United States v. Black, 201 F.3d 1296, 1299-1300 (10th Cir. 2000); see also

Yazzie, 407 F.3d at 1142. We review the district court’s denial of a motion to

withdraw for an abuse of discretion. United States v. Jones, 168 F.3d 1217, 1219

(10th Cir. 1999). Although a district court should generally freely allow a

defendant to withdraw a guilty plea, we will not reverse the court’s denial of such

a motion unless the defendant shows that the court acted “unjustly or unfairly.”

United States v. Kramer, 168 F.3d 1196, 1202 (10th Cir. 1999).

      Analyzing the relevant factors, the district court concluded that each

consideration weighed against allowing Hasson to withdraw his plea. We fail to

discern any abuse of discretion in that decision.

                                        -10-
      To begin with, Hasson has never asserted his legal or factual innocence to

the two counts to which he pleaded guilty. See Hamilton, 510 F.3d at 1214

(reasoning that a defendant may satisfy the first factor by asserting legal or

factual innocence). He admitted to the factual basis underpinning those counts at

his change of plea hearing, and he has not since repudiated that admission. See

id. at 1215. To be sure, his plea withdrawal was premised not on an assertion of

innocence but instead on a claim that he misunderstood his potential sentencing

exposure. That is insufficient to satisfy his burden of showing that he has

asserted either his factual or legal innocence.

      The other relevant factors also weigh against Hasson. As for prejudice to

the government, it would be required to prepare for an unanticipated trial. In a

case such as this, which the court designated as complex under 18 U.S.C.

§ 3161(h)(8)(B)(ii), the prejudice to the government is more obvious because trial

preparation would entail considerable effort. Hasson also delayed the filing of his

withdrawal motion until just days before sentencing, having waited almost four

months after entering his guilty plea. See Carr, 80 F.3d at 420 (reasoning that a

three-month delay in filing a motion to withdraw a plea weighs against the

defendant); United States Vidakovich, 911 F.2d 435, 439-40 (10th Cir. 1991)

(recognizing that a five-month delay weighs against the defendant). The fourth

and seventh factors, which consider the waste of the resources of the court and

the potential for inconvenience to it, similarly favor denying withdrawal of the

                                         -11-
plea. See United States v. Graham, 466 F.3d 1234, 1239 (10th Cir. 2006)

(recognizing that these two factors “trigger[] similar concerns”). Scheduling a

last-minute trial in a complex case would necessarily disrupt the court’s docket

and cause delays in other cases. Considering the anticipated length of a trial in

this case, which the district court estimated at approximately two weeks, the court

would suffer substantial inconvenience. Moreover, prior to accepting the plea,

the trial court had already spent a great deal of time crafting a tailored set of

pretrial deadlines. If the court were to permit the plea to be withdrawn, it would

have to retread much of the ground it had already covered. See United States v.

Siedlik, 231 F.3d 744, 750 (10th Cir. 2000).

      Although Hasson raises an allegation of ineffective assistance of counsel,

we cannot conduct a comprehensive review of that issue for the reasons

discussed. We note only that Hasson had two trial lawyers at his side when he

entered his plea, that the district court gave him numerous opportunities to

procure the counsel of his choosing, and that he never alleged below that he was

in any way dissatisfied with the attorneys who assisted him in entering the plea.

Indeed, at his change of plea hearing, Hasson responded in the affirmative to the

court’s inquiry regarding whether he was “fully satisfied with the legal advice,

with the counsel, with the services that [had] been provided to [him] in this case

by [his] attorneys.” The district court did not err in concluding that this factor

weighed against his request.

                                         -12-
      Finally, there is no indication in the record that the plea was anything but

knowingly and voluntarily given. During his change of plea hearing, Hasson

acknowledged that he was giving the plea “freely of [his] own will,” that he had

not been “forced . . . to plead guilty in this case,” and that he had read the plea

agreement and indictment. He further agreed that he had discussed the documents

with his attorneys, that he had no questions about the documents, and that he

understood all of the rights he was waiving by entering a guilty plea. We are thus

satisfied that the district court did not abuse its discretion in rejecting Hasson’s

belated attempt to withdraw his plea. His conviction is therefore affirmed.

                                          III

      We now address the final issue presented: Hasson’s challenge to the

procedural reasonableness of his sentence. Hasson maintains that the district

court miscalculated his advisory Guidelines range by grouping the two separate

counts of conviction before applying the specific-offense-characteristic increase

required by U.S.S.G. § 2S1.1(b)(2)(B) to his Count 3 base offense level. We

review the district court’s legal application of specific guidelines de novo, and

review any facts found in support of those guidelines for clear error. United

States v. Todd, 515 F.3d 1128, 1135 (10th Cir. 2008).

      As the government concedes, there is little question that the PSR

incorrectly applied the two-level increase mandated by § 2S1.1(b)(2)(B) after,

rather than before, grouping the separate counts of conviction under § 3D1.2(d).

                                         -13-
The Guidelines plainly prescribe a step-by-step process for calculating a

defendant’s total offense level. See § 1B1.1; see also United States v. Ventura,

353 F.3d 84, 92 (1st Cir. 2003) (describing offense-level calculation process).

First, when a defendant is convicted of multiple counts, the sentencing court is

obliged to separately determine the offense level for each count. See § 1B1.1(d);

see also United States v. Liddell, 492 F.3d 920, 924 (7th Cir. 2007) (“The

guidelines explicitly state that district courts should compute sentencing guideline

ranges on a count-by-count basis.”). Once the base offense level for each count

has been determined, the court must then apply any appropriate specific offense

characteristics from Chapter Two of the Guidelines, § 1B1.1(b), and then any

relevant adjustments from the first three parts of Chapter Three of the Guidelines,

§ 1B1.1(c). Only at that point may the court group various counts together, if

required, and adjust the overall offense level. § 1B1.1(d).

      In this case, the district court, relying on the PSR, transposed two of the

requisite steps and thereby miscalculated the appropriate sentencing range. By

grouping the two separate counts of conviction before it applied

§ 2S1.1(b)(2)(B)’s specific offense characteristic for Count 3, the court added two

levels to the grouped offense level that should have been added only to Count 3’s

base offense level. 6 This had the effect of overstating Hasson’s total offense level

      6
         Although the error had no net effect on the total offense level calculation
in this case and Hasson does not challenge it on appeal, we note that the PSR also
incorrectly grouped the separate counts of conviction together before applying the

                                        -14-
by two levels. As a result, Hasson’s advisory Guidelines range for Count 1 was

miscalculated as being between 292 and 365 months when it should have ranged

from 235 to 293 months. 7

      When the Guidelines range has been miscalculated, we must remand for

resentencing unless the error is harmless. See United States v. Kristl, 437 F.3d

1050, 1055 (10th Cir. 2006). Harmlessness must be proven by a preponderance of

the evidence and requires a showing that the error did not affect the district

court’s sentence selection. United States v. Conlan, 500 F.3d 1167, 1170 (10th

Cir. 2007). The burden of making this showing falls on the beneficiary of the

error—in this case, the government. Id.

      When a defendant is sentenced at the bottom of the sentencing range and

the district court committed procedural error in imposing that sentence, there is a

strong indication that, absent the error, the district court might have selected a

lesser sentence. See, e.g., United States v. Lozano, 514 F.3d 1130, 1135-36 (10th



role-in-the-offense adjustment under § 3B1.1(a). See § 1B1.1(c)-(d).
      7
        In accordance with the plea agreement’s stipulations, which the PSR and
the district court accepted, the base offense level for Count 3 was properly set at
32. It should have then been increased by 2 levels under § 2S1.1(b)(2)(B), which
would have yielded an offense level of 34 for Count 3, the same offense level as
stipulated for Count 1. Adding the role-in-the-offense adjustment under
§ 3B1.1(a) (likely to Count 1 based on the PSR) would have provided an adjusted
offense level of 38 for Count 1. By then grouping the counts in accordance with
§ 3D1.2(d) and subtracting 3 levels for Hasson’s acceptance of responsibility, the
PSR would have resulted in a total offense level of 35 for the combined counts, or
two levels lower than that indicated in the PSR.

                                         -15-
Cir. 2008); Conlan, 500 F.3d at 1170. Such is the case here. Had the district

court sentenced Hasson at the bottom of a correctly calculated Guidelines range,

he would have received a sentence of 235 months’ imprisonment, or some 57

months fewer than the sentence he received. Accordingly, we reverse and remand

for resentencing.

                                        IV

      In light of the foregoing, we AFFIRM Hasson’s convictions, but

REVERSE and REMAND his sentence to the district court with instructions to

vacate and resentence the defendant.


                                       ENTERED FOR THE COURT



                                       Carlos F. Lucero
                                       Circuit Judge




                                        -16-
