* Judge Pickering was a member of the original panel but

resigned from the Court on December 8, 2004 and therefore did not

participate in this decision. This matter is being decided by a

quorum. 28 U.S.C. § 46(d).

United States Court of Appeals

Fifth Circuit

FILED

May 20, 2005

Charles R. Fulbruge III

Clerk

REVISED JULY 1, 2005

IN THE UNITED STATES COURT OF APPEALS

FOR THE FIFTH CIRCUIT

_____________________

No. 03-30437 

_____________________

UNITED STATES OF AMERICA

Plaintiff - Appellee

v.

FRANCISCO D PINEIRO, also known as Frank Pineiro

Defendant - Appellant

_________________________________________________________________

Appeal from the United States District Court

for the Western District of Louisiana

_________________________________________________________________

ON REMAND FROM THE SUPREME COURT OF THE UNITED STATES

Before KING, Chief Judge, and BARKSDALE, Circuit Judge.*

PER CURIAM:

Defendant Francisco D. Pineiro was convicted in the United

States District Court for the Western District of Louisiana of

violating the federal controlled-substances laws. During

sentencing, the district judge made various fact findings to

determine Pineiro’s sentencing range under the then-mandatory
1 Pineiro was also convicted of: (1) possessing and aiding

and abetting possession with intent to distribute approximately

three-fourths of a pound of marijuana in violation of 21 U.S.C.

§ 841(a)(1) and 18 U.S.C. § 2; and (2) possessing and aiding and

abetting possession with intent to distribute approximately

twenty-one pounds of marijuana in violation of 21 U.S.C.

§ 841(a)(1) and 18 U.S.C. § 2. 

2

U.S. Sentencing Guidelines. Pineiro objected to these judge-made

findings. His objections were overruled, and he subsequently

appealed his sentence to this court. Reasoning that the holding

in Blakely v. Washington, 124 S. Ct. 2531 (2004), did not apply

to the U.S. Sentencing Guidelines, we affirmed Pineiro’s

sentence. United States v. Pineiro, 377 F.3d 464 (5th Cir.

2004). Pineiro then filed a petition for certiorari to the

Supreme Court. The Supreme Court granted certiorari, vacated

this court’s judgment, and remanded the case for further

consideration in light of United States v. Booker, 125 S. Ct. 738

(2005). Because we find that the Sixth Amendment Booker error

was not harmless, we now VACATE Pineiro’s sentence and REMAND to

the district court for resentencing. 

I. BACKGROUND

Pineiro was convicted by a jury of conspiracy to distribute

“less than 50 kilograms” of marijuana and “50 grams or less” of

cocaine, in violation of 21 U.S.C. §§ 841(a)(1) and 846.1 The

Presentence Investigation Report (“PSR”) indicated that Pineiro

was responsible for drug amounts much greater than the amounts

found by the jury. Specifically, the PSR stated that Pineiro was
2 Pineiro was also sentenced to sixty months on each of

the possession with intent to distribute convictions, with the

sentences to run concurrently.

3

responsible for 453.6 kilograms of marijuana and 1,048.95 grams

of cocaine. Based on these quantities of drugs, the PSR

concluded that Pineiro’s base offense level for the conspiracy

conviction was twenty-eight. See UNITED STATES SENTENCING GUIDELINES

[hereinafter “U.S.S.G.” or the “Guidelines”] § 2D1.1(c). The PSR

further recommended that Pineiro receive a four-level sentence

enhancement under U.S.S.G. § 3B1.1(a) for being an “organizer or

leader” of the conspiracy. The resulting total offense level of

thirty-two, when combined with Pineiro’s criminal history

category of I, yielded a Guidelines range of 121 to 151 months. 

Pineiro objected to the PSR on several grounds. First, he

objected to the base offense level of twenty-eight, arguing that

using the larger drug quantities would violate the rule

articulated in Apprendi v. New Jersey, 530 U.S. 466 (2000). 

Second, he objected to the four-level “organizer or leader”

enhancement on the ground that the evidence at trial did not

support such a factual finding, but he did not raise a

constitutional claim regarding this enhancement. The district

court overruled Pineiro’s objections and sentenced him to 121

months on the conspiracy conviction.2 Pineiro appealed his

sentence to this court. 
3 As to the sentence enhancement for being a leader or

organizer, Pineiro did not claim that his fact-based objection to

the PSR was sufficient to preserve the constitutional issue; he

did, however, claim that the district court committed reversible

plain error in light of Blakely. 

4

While Pineiro’s appeal was pending before us, the Supreme

Court decided Blakely. At our request, the parties submitted

supplemental briefing to assess Blakely’s impact. Pineiro

contended that the Supreme Court’s holding in Blakely applied to

the Guidelines and that his sentence must be vacated and the case

remanded for resentencing.3 This court disagreed and affirmed

Pineiro’s sentence. Pineiro, 377 F.3d at 464. Pineiro then

filed a petition for certiorari. 

On January 12, 2005, the Supreme Court decided Booker, in

which it held that when a sentencing judge bound by mandatory

Guidelines has increased the defendant’s sentencing range based

on facts not found by a jury or admitted by the defendant, the

sentence violates the defendant’s Sixth Amendment right to a jury

trial. Booker, 125 S. Ct. at 755-56. In its Remedy Opinion, the

Court effectively converted the Guidelines from a mandatory

regime to an advisory regime. Id. at 756. Accordingly, the

Court vacated our judgment in Pineiro, and it remanded the case

to us for further consideration in light of Booker. On March 3,

2005, we ordered the parties to file letter briefs setting forth

the disposition we should make of this appeal in light of Booker. 

In his letter brief, Pineiro argues that the district court
4 This court has previously noted that there has been some

suggestion that harmless error will not apply to preserved Sixth

Amendment Booker claims. See United States v. Akpan, No.

03-20875, 2005 WL 852416, at *12 n.55 (5th Cir. Apr. 14, 2005)

(citing United States v. Oliver, 397 F.3d 369, 381 (6th Cir.

2005)); cf. United States v. Rodriguez, No. 04-12676, 2005 WL

895174, at *20 (11th Cir. Apr. 19, 2005) (Tjoflat, J.,

dissenting). That view originates from the statement in Booker

that “in cases not involving a Sixth Amendment violation, whether

resentencing is warranted or whether it will instead be

sufficient to review a sentence for reasonableness may depend

upon application of the harmless-error doctrine.” 125 S. Ct. at

769. To conclude that cases involving Sixth Amendment Booker

error are not subject to harmless error analysis not only reads

too much into that sentence, see Rodriguez, 2005 WL 895174, at *4

(Carnes, J., concurring) (stating that drawing instruction from

Supreme Court passages through the use of a negative pregnant is

generally unsatisfactory and particularly unsatisfactory in this

case because it contradicts Booker’s clear directive that every

Booker appeal will not lead to a new sentencing hearing because

reviewing courts should apply ordinary prudential doctrines such

as plain error), but it also contradicts this court’s precedent. 

See United States v. Mares, 402 F.3d 511, 520 n.9 (stating that

harmless error applies to preserved Sixth Amendment error

claims). Furthermore, those circuits that have addressed

preserved Sixth Amendment Booker claims to date have applied

harmless error. See, e.g., United States v. Medley, No. 03-2026,

2005 WL 914848 (10th Cir. Apr. 21, 2005); United States v.

Coumaris, 399 F.3d 343, 351 (D.C. Cir. 2005). Thus, harmlesserror analysis applies.

5

committed reversible error and that this court must therefore

remand for resentencing. The government, on the other hand,

argues that the district court’s error was harmless.

II. ANALYSIS

“[I]f either the Sixth Amendment issue presented in Booker

or the issue presented in Fanfan is preserved in the district

court by an objection, we will ordinarily vacate the sentence and

remand, unless we can say the error is harmless under Rule 52(a)

of the Federal Rules of Criminal Procedure.”4 United States v.
6

Mares, 402 F.3d 511, 520 n.9 (5th Cir. 2005); see also United

States v. Olano, 507 U.S. 725, 734 (1993) (noting that harmless

error applies when a defendant makes a timely objection to an

error). Rule 52(a) states that “[a]ny error, defect,

irregularity, or variance that does not affect substantial rights

must be disregarded.” FED. R. CRIM. P. 52(a). An error affects

substantial rights (i.e., is prejudicial) if it affects the

outcome of the district court proceedings. Olano, 507 U.S. at

734; United States v. Akpan, No. 03-20875, 2005 WL 852416, at *12

(5th Cir. Apr. 14, 2005); United States v. Munoz, 150 F.3d 401,

413 (5th Cir. 1998). Consequently, an error is deemed harmless

if it did not affect the outcome of the district court

proceedings. Olano, 507 U.S. at 734; Akpan, 2005 WL 852416, at

*12; Munoz, 150 F.3d at 413. The government bears the burden of

showing that the error was harmless beyond a reasonable doubt. 

Olano, 507 U.S. at 734 (noting that the inquiry to determine

prejudice is the same between plain-error and harmless error, but

that the defendant, rather than the government, bears the burden

of persuasion with respect to prejudice under plain error

review); Chapman v. California, 386 U.S. 18, 24 (1967) (holding

that “before a federal constitutional error can be held harmless,

the court must be able to declare a belief that it was harmless

beyond a reasonable doubt”); Akpan, 2005 WL 852416, at *12. 

Thus, to show harmlessness, the government must demonstrate

beyond a reasonable doubt that the Sixth Amendment Booker error
5 In our previous opinion in this case, we concluded that

Pineiro’s Apprendi-based objection was sufficient to preserve his

Blakely challenge to his sentence. Pineiro, 377 F.3d at 467 n.4

(citing United States v. Doggett, 230 F.3d 160, 162-63, 165 (5th

Cir. 2000)).

7

did not affect the sentence that the defendant received. Akpan,

2005 WL 852416, at *12 (citing Munoz, 150 F.3d at 413, and

Chapman, 386 U.S. at 24).

Pineiro’s Apprendi-based objection to the PSR’s

drug-quantity calculations was sufficient to preserve his Booker

claim because he challenges his sentence based on the same

constitutional violation addressed by both cases.5 See Booker,

125 S. Ct. at 756-57 (reaffirming and applying to the federal

sentencing guidelines the holding in Apprendi that any fact

(other than a prior conviction) that increases the penalty of a

crime beyond the statutory maximum must be admitted by the

defendant or proved to a jury beyond a reasonable doubt); see

also United States v. Bailey, 405 F.3d 102, 113-14 (1st Cir.

2005) (reviewing a defendant’s Booker claim under plain error

because he made no arguments in the district court concerning the

constitutionality of the Guidelines or the application of the

Guidelines to his sentence under Blakely or Apprendi); United

States v. Windrix, Nos. 04-5016, 04-5020, 04-5021, 2005 WL

1023398 (10th Cir. May 3, 2005) (rejecting the government’s

argument that the defendants did not preserve their Booker

objection when they objected to the enhancements made to their
8

sentences under Apprendi); United States v. Dowling, 403 F.3d

1242, 1246 (11th Cir. 2005) (concluding that the defendant did

not preserve a Booker claim because he did not make a

constitutional objection at sentencing, which includes citing

Apprendi, the Sixth Amendment, or the defendant’s right to have

facts found by a jury instead of a judge). Accordingly, we

review for harmless error. Here, there is no question that the

district court committed Sixth Amendment Booker error by

enhancing Pineiro’s sentence pursuant to its finding that he was

responsible for a greater quantity of drugs than that for which

the jury found him responsible. See Booker, 125 S. Ct. at 738. 

The question remains whether that error was harmless. Thus, we

must ascertain whether the government has met its burden of

showing beyond a reasonable doubt that the error did not affect

the outcome of the district court proceedings, i.e., that the

district court would have imposed the same sentence absent the

error. 

The government points to evidence in the record in an

attempt to meet its burden. It first points to the fact that the

sentencing judge stated that he knew of no reason to depart

upward or downward and thus that he would adhere to the

Guidelines. It is clear, however, upon reading the sentencing

judge’s remarks in their entirety that he could find no reason to

depart upwardly or downwardly under the provisions of the thenmandatory Guidelines precisely because he was restricted by the
6 The sentencing judge stated:

Mr. Pineiro, you do understand, and I’m sure your

attorney has told you, that the Court in meting out

sentencing, this and virtually every other case that

comes before the Court, I’m bound by sentencing

guidelines [that are] prepared by the United States

Sentencing Commission. So I have to operate within those

[parameters], unless there are certain reasons why the

guidelines can be bent[. F]or example, with substantial

cooperation, the government can file a motion for a

downward departure based on substantial assistance by a

defendant, and the Court can depart. In that regard, the

Court can also depart upward in certain cases where there

are . . . aggravating circumstances not fully taken under

consideration by the guidelines. I don’t know of [any]

reason in this case why either –- there should be either

an upward or a downward departure from the guidelines.

So to that extent, the Court will adhere to the

guidelines. 

9

Guidelines.6 The judge’s statement certainly does not suggest

that even under an advisory scheme he would know of no reason to

depart upwardly or downwardly. 

Secondly, the government notes that at no point during the

sentencing hearing did the judge say that Pineiro’s Guidelines

range was too high in light of his offense, or that the court

would impose a lower sentence if not bound by the Guidelines. 

Although this argument would be persuasive under plain-error

review, this argument fails to show that the preserved error was

harmless. It is the government that must show that the

sentencing judge would have imposed the same sentence under an

advisory sentencing scheme. The judge’s silence as to whether or

not he would have imposed a different sentence under an advisory

regime does not satisfy this burden. If we were to accept this
7 Because we remand for resentencing based on the drugquantity enhancement, we do not reach Pineiro’s argument with

respect to the organizer-or-leader enhancement. 

10

argument to find that the error was harmless, we would

effectively be relieving the government of its burden and placing

it on the defendant. 

Finally, the rest of the government’s arguments simply

attempt to undercut Pineiro’s assertions that the sentencing

judge made statements tending to suggest he would have imposed a

lower sentence under an advisory scheme. First, the government

argues that the sentencing judge’s displeasure with sentencing

Pineiro was not based on the fact that he was bound by mandatory

Guidelines, but rather that Pineiro maintained his innocence,

which in turn caused his family to question the integrity of the

justice system. Second, the government asserts that the

sentencing judge’s statement that drug sentences were “pretty

harsh” was part of a larger complaint about the relatively

lenient sentences the Guidelines provided for economic crimes. 

These arguments are clearly insufficient to satisfy the

government’s arduous burden. We therefore conclude that the

government has failed to meet its burden of showing beyond a

reasonable doubt that the district court would have imposed the

same sentence under an advisory scheme.7 Thus, Pineiro is

entitled to resentencing in accordance with Booker. 

III. CONCLUSION
11

Accordingly, we VACATE the defendant’s sentence, and REMAND

for resentencing.