United States v. Serrano-Beauvaix

United States Court of Appeals
For the First Circuit

No. 02-2286
02-2682
UNITED STATES OF AMERICA,

Appellee,

v.

JOSE SERRANO-BEAUVAIX; MAHMUD JUMA-PINEDA,

Defendants, Appellants.

APPEALS FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF PUERTO RICO

[Hon. José Antonio Fusté, U.S. District Judge]

Before

Torruella, Lynch, and Lipez, Circuit Judges.

Mark Diamond for appellant Jose Serrano-Beauvaix.
George J. West for appellant Mahmud Juma-Pineda.
Thomas F. Klumper, Assistant United States Attorney, with whom
H.S. Garcia, United States Attorney, and Nelson Pérez-Sosa,
Assistant United States Attorney, Senior Appellate Attorney, were
on brief, for appellee.

March 4, 2005
 LYNCH, Circuit Judge. Jose Serrano-Beauvaix and Mahmud

Juma-Pineda were participants in a large conspiracy which

transported drugs under the protection of corrupt police officers

in the Puerto Rico Police Department. The conspiracy is described

in United States v. Flecha-Maldonado, 373 F.3d 170, 172-74 (1st

Cir. 2004), upholding the conviction of one of Serrano's and Juma's

co-conspirators.

In brief, Serrano, a former police officer who had been

expelled from the force, helped to recruit Juma, a police officer

at the time, to provide armed escort for a shipment of ten

kilograms of cocaine in October, 2000. Juma rode with the drugs

and carried a pistol. Serrano rode in another car and conducted

counter-surveillance and advised his codefendants through cell

phones. They each received a $5000 payment for their services in

the crime.

Each defendant pled guilty to charges of conspiracy to

distribute in excess of five kilograms of cocaine in violation of

21 U.S.C. §§ 841(a) and 846 (Count One), and of carrying firearms

(and aiding and abetting of same) in furtherance of a drug

trafficking crime in violation of 18 U.S.C. §§ 924(c)(1)(A)(i) and

2 (Count Three). Each defendant stipulated to being personally

responsible for one kilogram of cocaine. In the plea agreements,

each also agreed to certain sentencing enhancements and

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acknowledged that each did not qualify for safety-valve treatment

under the Sentencing Guidelines.

Serrano was sentenced to 63 months' imprisonment for

Count One and a consecutive term of 60 months for Count Three.

Juma was sentenced to 60 months' imprisonment for Count One and a

consecutive term of 60 months for Count Three.

Serrano appeals from his conviction for the firearms

count, contending that his guilty plea was procedurally flawed

under Fed. R. Crim. P. 11(b)(3).1 We reject this argument because

there was no error during the Rule 11 colloquy. Serrano and Juma

both appeal their sentences, raising a variety of arguments, most

of which were waived by their plea agreements. Serrano also raises

a claim of plain error as to his sentence under United States v.

Booker, 543 U.S. __, 125 S. Ct. 738 (2005). We reject this

argument as well because Serrano has failed to carry his burden

that there is a "reasonable probability" that he would be sentenced

more leniently under an advisory Guidelines system. See United

States v. Antonakopoulos, No. 03-1384, 2005 WL 407365, at *4 (1st

Cir. Feb. 22, 2005).

1
Rule 11(b)(3) resulted from the recodification of its
predecessor, Rule 11(f), in December of 2002. See United States v.
Ventura-Cruel, 356 F.3d 55, 60 n.5 (1st Cir. 2003). However, the
change in language between Rule 11(b)(3) and Rule 11(f) is only
stylistic. Id.

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 I.

A. Serrano's Appeal

1. The Guilty Plea To Count Three

Serrano argues for the first time on appeal that the

district court erred procedurally in accepting his guilty plea to

Count Three. His argument is that the district court failed to

"explore the factual basis of the guilty plea" as required by Fed.

R. Crim. P. 11(b)(3), which states: "Before entering judgment on a

guilty plea, the court must determine that there is a factual basis

for the plea." Serrano argues that had the district court done so,

it would have found that there was no factual basis for Serrano's

guilty plea because Serrano only admitted to providing "armed

transport" for the drug shipment, but not to having possessed a

firearm. The admission that he was "armed" was insufficient, he

now argues, because it might have meant that he was "armed with a

big stick."

We review a Rule 11 challenge raised for the first time

on appeal only for plain error. United States v. Vonn, 535 U.S.

55, 74-76 (2002); United States v. Cheal, 389 F.3d 35, 40 (1st

Cir. 2004); see also United States v. Mills, 329 F.3d 24, 27 (1st

Cir. 2003) ("An error not objected to at the plea hearing is

reversible only where the error is plain, affects the defendant's

substantial rights, and seriously affects the fairness of the

proceeding."). As to the underlying issue of compliance with the

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Rule, "[o]n a plea, the question under Rule 11(f) [now Rule

11(b)(3)] is not whether a jury would, or even would be likely, to

convict: it is whether there is enough evidence so that the plea

has a rational basis in facts that the defendant concedes or that

the government proffers as supported by credible evidence." United

States v. Gandia-Maysonet, 227 F.3d 1, 6 (1st Cir. 2000). In this

case, there was no error.

Serrano's argument mischaracterizes his plea colloquy by

ignoring the aiding and abetting and in furtherance of the

conspiracy aspects of the charge against him in Count Three. The

district court's Rule 11 colloquy focused on those aspects of the

charge. It is irrelevant whether there were facts to show that

Serrano was personally armed with a gun or a big stick. During the

Rule 11 colloquy, Serrano specifically agreed that in "aiding and

abetting each other a gun was possessed in furtherance of the

conspiracy" (emphasis added). Furthermore, Serrano's counsel

explained that Serrano understood that although he "did not carry

the firearm" (emphasis added), he was responsible for the

firearm(s) carried by his codefendant(s) under Pinkerton v. United

States, 328 U.S. 640 (1946). Rule 11(b)(3) is meant to "protect a

defendant who is in the position of pleading voluntarily with an

understanding of the nature of the charge but without realizing

that his conduct does not actually fall within the charge."

McCarthy v. United States, 394 U.S. 459, 467 (1969) (footnote and

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internal quotation marks omitted). The district judge ascertained

that Serrano understood that he could be held liable for the

firearms charge without having carried the gun himself and that

Serrano was aware of the gun Juma possessed as part of the "armed

escort" they provided for the drug shipment.

2. The Sentence for Count One

Serrano brings a trio of challenges to his sentence as to

Count One,2 and argues that we should remand to the district court

for resentencing in light of United States v. Booker, 543 U.S. __,

125 S. Ct. 738 (2005). First, he challenges the evidentiary

support for his criminal record and his organizer role sentencing

enhancement; second, he argues that the district court was

constrained by the mandatory Sentencing Guidelines and so

sentenced him to above the statutory minimum; third, he argues that

he should have been given the benefit of the safety valve. We take

up each challenge in turn.

2
Serrano's sentence was computed as follows: The stipulated
drug amount established a base offense level of 26. U.S.S.G. §
2D1.1(c)(7). This base offense level was enhanced by two levels
because of his role as an "organizer, leader, manager, or
supervisor" and reduced by three levels because of his acceptance
of responsibility, yielding a final offense level of 25. See
U.S.S.G. §§ 3B1.1(c), 3E1.1(a)-(b). The base offense level and the
enhancement calculations were all made a part of the plea agreement
signed by the defendant. His criminal history score was 3, which
placed him in criminal history category II. The Guidelines range
was therefore 63-78 months. U.S.S.G. Ch. 5 Pt. A. The statutory
minimum under 21 U.S.C. § 841(b)(1)(B) for the offense Serrano pled
guilty to is 60 months.

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 i. We begin with Serrano's argument that there was no

factual support for either the finding 1) that Serrano's role

during the offense was that of an "organizer, leader, manager, or

supervisor," justifying an increase in his offense level by two

levels, see U.S.S.G. § 3B1.1(c), or 2) that Serrano's criminal

history placed him in criminal history category II.3 If the

district court erred in making these findings and, as a result,

misapplied sentencing enhancements under the Guidelines so as to

cause prejudice to Serrano's sentence, the errors would justify

remand for resentencing even under pre-Booker circuit precedent.

See, e.g., United States v. Thiongo, 344 F.3d 55, 63 (1st Cir.

2003); United States v. McMinn, 103 F.3d 216, 219 (1st Cir. 1997).

Serrano has waived his challenge to his organizer role

enhancement. The plea agreement stipulated that Serrano "helped

[another codefendant] contact and recruit a police officer to

assist in the escort of the cocaine shipment." The plea agreement

also included the stipulation that Serrano's offense level would be

adjusted upwards by two levels under § 3B1.1 because he "recruited

one of his co-defendants." The district judge ascertained that

Serrano understood and agreed to this adjustment. At sentencing,

3
Without the role-enhancement, Serrano's final offense level
would have been 23, and combined with a criminal history category
of II, would have produced a Guidelines sentencing range of 51-63
months. U.S.S.G. Ch. 5 Pt. A. Similarly, if Serrano's criminal
history category had been I, that, combined with a final offense
level of 25, would have produced a Guidelines range of 57-71
months. Id.

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Serrano made no objection to the finding that he recruited a

codefendant.

As for Serrano's criminal history, "[o]nce the government

establishes the existence of a prior conviction, the burden shifts

to the defendant to show that the earlier conviction was

constitutionally infirm or otherwise inappropriate for

consideration." United States v. Barbour, 393 F.3d 82, 93 (1st

Cir. 2004). At Serrano's detention hearing, his counsel stipulated

to a criminal conviction in Humacao for violating Puerto Rico

weapons laws. Serrano's pre-sentencing report (PSR), "which can be

used to satisfy the government's 'modest' burden," id. (quoting

United States v. Gray, 177 F.3d 86, 89 (1st Cir. 1999)), detailed

Serrano's prior conviction in commonwealth court in Humacao for

violating Puerto Rico weapons laws and calculated his criminal

history score to be 3. Serrano made no objection to his criminal

history score in the PSR at his sentencing hearing. Serrano

conceded that "the probation officer has to follow what convictions

[Serrano] has in the police of Puerto Rico records." In fact, the

only "correction" that Serrano's counsel wished to make to the PSR

was to "reference . . . the actual number of the criminal case in

Humacao," and the court agreed. Serrano admitted to this

conviction at the sentencing hearing, but suggested as a

"mitigating argument" that he had a "solid alibi defense." The

district court properly rejected this argument.

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 ii. Serrano next argues that his sentence on Count One should

be vacated and the case remanded for resentencing because the

district court was clearly constrained by the Guidelines during

sentencing and imposed the 63-month term, which was above the

statutory minimum of 60 months, and was at the bottom of the

applicable Guidelines range. Post Booker, Serrano argues, the

district court could have (and would have) sentenced him to the

statutory minimum of 60 months. Serrano made no arguments in the

district court questioning the constitutionality of the Guidelines

or the application of the Guidelines to his sentence under Apprendi

v. New Jersey, 520 U.S. 466 (2000), or Blakely v. Washington, 542

U.S. __, 124 S. Ct. 2531 (2004), so the Booker issue was not

preserved. See Antonakapolous, 2005 WL 407365, at *6.

We have recently set forth the applicable framework for

review of unpreserved Booker claims in Antonakopoulos. Utilizing

the four-prong test in United States v. Olano, 507 U.S. 725 (1993),

there must be (1) an error (2) that is plain, and it (3) affects

substantial rights and (4) seriously impairs the fairness,

integrity, or public reputation of judicial proceedings.

Antonakopoulos, 2005 WL 407365, at *4. The first two prongs of the

plain error test are met whenever the district court treated the

Guidelines as mandatory at the time of sentencing. Id. But to

meet the third prong of the test, the defendant must persuade us

that there is a "reasonable probability that the district court

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would impose a different sentence more favorable to the defendant

under the new 'advisory Guidelines' Booker regime." Id. "[I]t is

the defendant rather than the Government who bears the burden of

persuasion with respect to prejudice under plain-error analysis."

Id. at *6 (citations and internal quotation marks omitted).

Serrano relies upon the district judge's statement at the

sentencing hearing: "I have to consider the fact that I cannot

sentence him to 60 months. The lowest I can sentence him on that

particular situation is 63." This statement, he argues, makes it

"clear that the district court would have sentenced [Serrano] to 60

months in prison instead of 63 on count one." Not so. Given

Serrano's criminal history category and his role as recruiter, and

the amount of drugs involved, the court's statement was a simple

statement of fact. The statutory minimum, without the

enhancements, was 60 months. He was sentenced to 63 months, out of

a possible range of 63 to 78 months. Serrano's argument amounts to

an assertion that there was such a reasonable probability that the

judge would have totally ignored Serrano's role in the offense and

prior conviction and that our confidence in the outcome is

undermined by the fact that the judge actually considered these two

enhancements. Even post-Booker, the district court "must consult

those Guidelines and take them into account when sentencing."

Booker, 543 U.S. at __, 125 S. Ct. at 767. And so the court had to

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consider both role in the offense and his criminal history.

Serrano has failed to meet his burden.

iii. Serrano's final argument in his sentencing appeal is that

the district court committed error in denying him the benefit of

the provisions of the safety valve under 18 U.S.C. § 3553(f) and

U.S.S.G. § 5C1.2. The argument, raised for the first time on

appeal, is that but for the court's findings that Serrano had more

than one criminal history point and that Serrano was an organizer

of the criminal activity, he would have qualified for safety-valve

treatment and thus be entitled to sentencing without regard to any

statutory minimum.

The effect of Booker, if any, on the safety valve has not

been determined. See Antonakopoulos, 2005 WL 407365, at *6 n.6.

But Serrano's argument is waived because Serrano explicitly agreed

in his plea agreement that he did not qualify for safety-valve

treatment, and confirmed that he understood that he did not qualify

for the safety valve during his change of plea hearing.

B. Juma's Appeal of His Sentence

Juma first argues that the district court erred by

equating his carrying of his official police pistol during the

crime with disqualification from his entitlement to a downward

departure under the safety valve. See 18 U.S.C. § 3553(f) and

U.S.S.G. §§ 2D1.1(b)(7), 5C1.2. He argues that but for the finding

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that he carried his pistol during and in connection with the crime,

he would have qualified for safety-valve treatment and be sentenced

below the statutory minimum. Although he stipulated to having

"carried a pistol" during the escort in his plea agreement, Juma

contends that the district court erred by not considering that he

may nonetheless qualify for the safety valve because the firearm

was not clearly connected to the offense.4 See United States v.

Bolka, 355 F.3d 909, 914 (6th Cir. 2004).

This argument is waived because Juma explicitly agreed in

his plea agreement that he did not qualify for safety-valve

treatment, and confirmed that he understood that he did not qualify

for the safety valve during his change of plea hearing.

Juma's second argument is that a jury, not a judge,

should have made the factual determinations underlying his

disqualification for the safety valve and the abuse of public trust

enhancement. By pleading guilty he waived consideration of the

issues by a jury.

III.

Serrano's conviction and both defendants' sentences are

affirmed.

(Concurrence follows.)

4
During the drive to transport the drugs, Juma pulled out the
gun to clean it in plain view. Flecha-Maldonado, 373 F.3d at 173.

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 LIPEZ, Circuit Judge, with whom TORRUELLA, Circuit Judge,

joins, concurring. Recently, in United States v. Antonakopoulos,

No. 03-1384, 2005 WL 407365 (1st Cir. Feb. 22, 2005), a panel of

this court explained for the first time our standards for review of

unpreserved claims of sentencing error in the aftermath of United

States v. Booker, 543 U.S. __, 125 S. Ct. 738 (2005). That

decision is binding on subsequent panels. Eulitt v. Me. Dep't of

Educ., 386 F.3d 344, 349 (1st Cir. 2004) (in a multi-panel circuit,

newly constituted panels are bound by prior panel decisions). I

agree with the result of the application of Antonakopoulos to this

case. I write separately, however, to explain why, if I were free

to do so, I would take a different approach to reviewing

unpreserved claims of Booker error.

Before explaining my differing views, however, I want to

stress that I agree with much in Antonakopoulos. I agree with its

description of Booker error as inhering in the mandatory nature of

the sentencing guidelines, regardless of whether the sentence was

premised on any judge-found facts. I agree, too, that the

defendant has preserved a claim of Booker error if he argued below

that his sentence violated Apprendi v. New Jersey, 530 U.S. 466

(2000), or Blakely v. Washington, 542 U.S. __, 124 S. Ct. 2531

(2004), or that the guidelines were unconstitutional. I agree that

we should not remand cases automatically, either because a

defendant's sentence was enhanced on the basis of judge-found facts

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or because the sentence was imposed on the basis of mandatory

guidelines.

My one disagreement with Antonakopoulos is crucial,

however. I do not believe that we should require defendants

invoking unpreserved Booker error to make a specific showing of

prejudice (the reasonable probability of a different outcome) to

satisfy the third step of plain-error review. Rather, such error

should entitle the defendant to a presumption of prejudice, which

the government can then try to rebut. This approach, adopted by a

panel of the Sixth Circuit in United States v. Barnett, No. 04-

5252, 2005 WL 357015 (6th Cir. Feb. 16, 2005), is well grounded in

Supreme Court precedent and has been applied by our sister circuits

in other contexts "where the inherent nature of the error made it

exceptionally difficult for the defendant to demonstrate that the

outcome of the lower court proceeding would have been different had

the error not occurred." Id. at *9. I wish to explain further my

reasons for preferring this approach.

1. The difficulty of reconstructing
a hypothetical sentencing decision

Several courts of appeals considering unpreserved claims

of Booker error have emphasized the difficulty of speculating about

what a district-court judge would have done differently under an

advisory guidelines regime. The Fourth Circuit admitted that: "We

simply do not know how the district court would have sentenced

Hughes had it been operating under the regime established by

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Booker." United States v. Hughes, 396 F.3d 374, 381 n.8 (4th Cir.

2005). Similarly, the Sixth Circuit wrote that "even if we

conclude that the evidence is 'overwhelming and essentially

uncontroverted' we cannot know the length of imprisonment that the

district court judge would have imposed pursuant to this evidence

following Booker." United States v. Oliver, No. 03-2126, 2005 WL

233779, at *8 n.3 (6th Cir. Feb. 2, 2005) (quoting United States v

Cotton, 535 U.S. 625, 633 (2002)). The Eleventh Circuit, too,

after wondering what the district court might have done

differently, answered its own question:

The obvious answer is that we don't know. If the
district court judge in this case had the liberty of
increasing or decreasing Rodriguez's sentence above or
below the guidelines range, he might have given Rodriguez
a longer sentence, or he might have given a shorter
sentence, or he might have given the same sentence. The
record provides no reason to believe any result is more
likely than the other. We just don't know.

United States v. Rodriguez, No. 04-12676, 2005 WL 272952, at *9

(11th Cir. 2005).

Indeed, the Second Circuit found this problem so vexing

that it chose to ask the district courts directly whether, in their

judgment, "a nontrivially different sentence would have been

imposed" under advisory guidelines. United States v. Crosby, No.

03-1675, 2005 WL 240916, at *12 (2d Cir. Feb. 2, 2005). The Second

Circuit noted that

in many cases, it will be impossible to tell whether the
judge would have imposed the same sentence had the judge
not felt compelled to impose a Guidelines sentence. It

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 will also be impossible to tell what considerations
counsel for both sides might have brought to the
sentencing judge's attention had they known that they
could urge the judge to impose a non-Guidelines sentence.

Id. at *9. The court chose to solve the problem by remanding any

case with unpreserved Booker error to the district courts, which

would then decide if resentencing was required. Although I do not

favor the Second Circuit's remand approach, I understand the

concerns that motivated it. So, too, did a panel of the Sixth

Circuit in the Barnett decision.

2. Barnett and presumed prejudice in Olano

In Barnett, the court emphasized the difficulty faced by

defendants trying to demonstrate the prejudice that resulted from

the district court's application of mandatory guidelines, when

"well established case law substantially undermined any need or

incentive for sentencing courts pre-Booker to note their objections

and reservations in sentencing defendants under the then-mandatory

Guidelines." 2005 WL 357015, at *4. Consequently,

[i]t would be improper for this Court now to require
defendants such as Barnett to produce this type of
evidence--that sentencing courts had no reason to provide
under our pre-Booker case law--in order to establish that
their substantial rights have been affected. . . .
Instead of speculating as to the district court's
intentions in the pre-Booker world, and trying to apply
those intentions to predict the same court's sentence
under the post-Booker scheme, we are convinced that the
most prudent course of action in this case is to presume
prejudice. . . .

Id.

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 Barnett reads United States v. Olano, 507 U.S. 725

(1993), as suggesting that if a defendant would have extraordinary

difficulty making a specific showing of prejudice, then a

presumption of prejudice may be appropriate. Barnett, 2005 WL

357015, at *9. The government, of course, can try to rebut that

presumption. Id. at *12. The dissent in Barnett maintains,

however, that "the Supreme Court has never put its imprimatur on

the idea that we may presume prejudice in plain error review," id.

at *18. It supported that assertion by observing that Olano

devotes just a sentence to the issue and then refused to consider

it further.

That is not a fair reading of Olano. After first

positing a category of plain errors entitled to a presumption of

prejudice, the Court found no reason to place the specific plain

error cited by the defendant (the presence of alternate jurors

during jury deliberations) in that category. 507 U.S. at 735.

True, the Court declined to offer a strict definition of the

category, seeing no need to "address those errors that should be

presumed prejudicial if the defendant cannot make a specific

showing of prejudice." Id. Later, however, the Court did confront

the question of whether Olano's error would belong to such a

category, if it exists; it decided that "we see no reason to

presume prejudice here." Id. at 737. At the same time, the Court

allowed that "[t]here may be cases where an intrusion should be

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presumed prejudicial." Id. at 739. In fact, the Court framed the

basic inquiry of its decision as: "The question, then, is whether

the instant violation of Rule 24(c) prejudiced respondents, either

specifically or presumptively." Id. (emphasis added). Ultimately,

the Court did not think "that the mere presence of alternate jurors

entailed a sufficient risk of 'chill' to justify a presumption of

prejudice on that score." Id. at 741. Nevertheless, its analysis

forthrightly explored the possibility that some kinds of errors

would justify such a presumption.

Here, in appeals with unpreserved claims of Booker error,

we have been presented with such errors.1

3. Presumed prejudice in other contexts

Courts have presumed prejudice for errors that, by their

very nature, make a demonstration of prejudice exceptionally

difficult. The Sixth Circuit has presumed prejudice where

alternate jurors actually participated in the jury's deliberations

(unlike Olano, where they were merely present). See Manning v.

Huffman, 269 F.3d 720, 726 (6th Cir. 2001) ("[T]he Olano court made

it quite clear that in some situations a presumption of prejudice

is appropriate."). After all, there are "strict evidentiary

prohibitions against inquiring into the mental processes of the

1
I do not consider this approach foreclosed by Justice
Breyer's closing words commending to the courts of appeal "ordinary
prudential doctrines," like plain error. Booker, 125 S. Ct. at
769. Olano discussed presumption of prejudice in the context of
plain-error review.

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jury [that] would make it almost impossible for a defendant to show

that an alternate juror in fact prejudiced his case." Id. at 725

n.2. In Booker cases, defendants face similarly forbidding

speculation about the mental processes of a district-court judge if

given the opportunity to apply advisory sentencing guidelines.

Courts have presumed prejudice where the defendant has

been denied his right to allocution, that is, his opportunity to

present mitigating circumstances to the court before being

sentenced. In those cases, too, courts have presumed that the

defendant was prejudiced because of the extraordinary difficulty in

discerning the error's prejudicial effect. See United States v.

Reyna, 358 F.3d 344, 352-53 (5th Cir. 2004) (en banc), cert.

denied, 124 S. Ct. 2390 (2004). The Fifth Circuit noted that this

approach "avoids speculation as to what the defendant might have

said or argued to mitigate his sentence." Id. at 352. In United

States v. Adams, 252 F.3d 276 (3d Cir. 2001), the Third Circuit

stated that showing prejudice

would be an onerous burden for Adams [i.e., the
defendant] to meet. In order to prove that the error
actually "affected the outcome of the district court
proceedings," Adams would have to point to statements
that he would have made at sentencing, and somehow show
that these statements would have changed the sentence
imposed by the District Court. . . . But as the Supreme
Court explained in Olano, there may be some errors "that
should be presumed prejudicial if the defendant cannot
make a specific showing of prejudice." Olano, 507 U.S. at
735. Thus the question for us becomes: should we presume
prejudice when a district court violates a defendant's
right of allocution?

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252 F.3d at 287. The Third Circuit's answer was yes.2 In United

States v. Alba Pagan, 33 F.3d 125 (1st Cir. 1994), although we did

not explicitly use Olano's four-part test, we observed that

relieving a defendant of his burden to show prejudice can

compensate for cases where it would be extraordinarily difficult

for the defendant to do so. Consequently, we wrote that the denial

of right to allocution "ordinarily requires vacation of the

sentence imposed without a concomitant inquiry into prejudice.

This is so precisely because the impact of the omission on a

discretionary decision is usually enormously difficult to

ascertain." Id. at 130.

4. Other reasons for presuming prejudice

In addition to the difficulty of reconstructing a

hypothetical sentencing-court decision, there are three other

reasons that make the presumption of prejudice a sensible choice

for addressing unpreserved Booker error.

2
The Third Circuit has also presumed prejudice after a
constructive amendment of the indictment:

Similar to the plight of a defendant who is denied the
right of allocution, it is very difficult for a defendant
to prove prejudice resulting from most constructive
amendments to an indictment. . . . Therefore, we will
apply in the plain error context a rebuttable presumption
that constructive amendments are prejudicial (and thus
that they satisfy the third prong of plain error review).

United States v. Syme, 276 F.3d 131, 154 (3d Cir. 2002).

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 a. Difficulty of anticipating the error

Although some defendants preserved their claims of Booker

error in the way described in Antonakopoulos,3 others did not.

Perhaps they can be faulted for not doing what other defendants

did. Yet the fact remains that the status of the Guidelines was

uncertain until Booker was decided, and the adoption of the remedy

chosen in Booker for the Sixth Amendment violation (converting the

Guidelines from mandatory to advisory) surprised many in the legal

profession. Placing the burden on defendants to establish

prejudice for unpreserved errors ordinarily makes sense because

they ignored existing law that they could have invoked to avoid the

error. As the Supreme Court has explained, the "burden should not

be too easy" because the prejudice standard helps "to encourage

timely objections and reduce wasteful reversals by demanding

strenuous exertion to get relief for unpreserved error." United

States v. Dominguez Benitez, 542 U.S. __, 124 S. Ct. 2333, 2340

(2004).

Here, however, the “existing” law (the availability of

advisory guidelines) is an artifice of our rule that "a new rule

for the conduct of criminal prosecutions is to be applied

retroactively to all cases . . . pending on direct review . . .,

3
"The argument that a Booker error occurred is preserved if
the defendant below argued Apprendi or Blakely error or that the
Guidelines were unconstitutional." Antonakopoulos, 2005 WL 407365,
at *6.

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with no exception for cases in which the new rule constitutes a

'clear break' with the past." Griffith v. Kentucky, 479 U.S. 314,

328 (1987); see also Johnson v. United States, 520 U.S. 461, 467

(1997). In actuality, a demand by defendants pre-Booker that

district-court judges treat the guidelines as advisory would have

been rejected by most of them as an incorrect statement of the law.

Frankly, "it seems unfair to fault [the defendant] for failing to

raise at [sentencing] an objection based upon a rule that was not

announced until after the [sentencing] was concluded." United

States v. Barone, 114 F.3d 1284, 1294 (1st Cir. 1997) (citing

United States v. Collins, 60 F.3d 4, 7 (1st Cir. 1995)).

Perhaps defendants should be grateful that our rule of

retroactivity for cases pending on direct review allows any

possibility at all for resentencing. But the fact remains that a

greater willingness to acknowledge the likelihood of prejudice from

a dramatic change in the law like Booker does not reward

"sandbaggers" who hoard their objections to hedge against a result

not to their liking. There was no game-playing with a rule of law

not yet known.4

4
The Second Circuit has relied on an intervening change in
law to justify shifting the prejudice burden from the defendant to
the government: "In this Circuit, when the error results from an
intervening change in the law, we have applied a modified version
of the plain error doctrine whereby the burden is on the Government
to show that the error did not affect substantial rights." United
States v. Williams , No. 04-2882, 2005 WL 425212, at *5 n.7 (2d
Cir. Feb. 4, 2005); see also United States v. Viola, 35 F.3d 37,
41-42 (2d Cir. 1994), abrogated on other grounds by Salinas v.

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 b. Adminstrative burden

The administrative burdens of increased remands for

sentencing (a likely result of the presumption of prejudice

approach), while not insubstantial, would certainly be manageable,

given the limited universe of cases at issue and the relatively low

cost of correcting errors in sentencing. For example, the Second

Circuit estimated that, when Booker was decided, it had about 200

cases pending on direct review with sentences that might be

erroneous under the Supreme Court's new teaching:

Many of these will likely be remanded . . . . Some of
the remands will likely result in resentencing. We do
not regard that prospect as an undue burden on the proper
functioning of the criminal justice system in the federal
courts of this Circuit. On the contrary, we consider it
far preferable to leaving some materially erroneous

United States, 522 U.S. 52 (1997). At the same time, the Second
Circuit has wondered whether that so-called "modified version" has
been implicitly rejected by Johnson v. United States, 520 U.S. 461
(1997). See Williams, 2005 WL 425212, at *5 n.7; United States v.
Thomas, 274 F.3d 655, 688 n. 15 (2d Cir. 2001) (en banc).
Although I respect the Second Circuit's prudence, I find its
speculation puzzling. In Johnson, the district court had decided
for itself the issue of materiality in a perjury persecution,
instead of submitting it to the jury. After Johnson was convicted,
and before her appeal, the Supreme Court decided United States v.
Gaudin, 515 U.S. 506 (1995), which required materiality to be
submitted to the jury. The Supreme Court held that an appellate
court can correct an error that was not plain at trial, but became
so on appeal. Johnson confined its discussion of prejudice to
addressing petitioner's theory that her error should be considered
structural error and hence outside the ambit of Rule 52(b)
altogether. The Court was dubious. Ultimately, the Court did not
need to decide the issue because her case failed anyway at the
fourth step of the plain-error analysis because of the overwhelming
evidence of materiality. Johnson, 520 U.S. at 470. The issue of
presumed prejudice--whether justified by a change in law or by
other reasons--was simply not before the Court.

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 sentences in place simply because we cannot guess what
sentencing judges would have done.

United States v. Williams, No. 04-2882, 2005 WL 425212, at *8 (2d

Cir. Feb. 4, 2005). These cases are a closed set. As soon as the

Supreme Court issued its opinion in Booker, district courts knew to

stop sentencing defendants under mandatory guidelines, thus

ensuring that no more cases will be tainted with Booker error.

Besides the simple numbers involved, we must consider

that resentencing in cases still pending on direct review does not

undermine the judicial system's high stakes in finality. By

definition, the cases we address here are not final. Moreover,

resentencing does not pose the burden of a new trial, with its

considerable costs in time, money, and other resources. As the

Second Circuit observed in Williams, "the cost of correcting a

sentencing error is far less than the cost of a retrial. A

resentencing is a brief event, normally taking less than a day and

requiring the attendance of only the defendant, counsel, and court

personnel." Williams, 2005 WL 425212, at *8. Given what is at

stake in sentencing decisions--the potential for additional months

or even years in prison--I believe that the increased

administrative burdens are a tolerable price to pay.

c. Possibility of rebuttal

A presumption of prejudice still permits rebuttal by the

government, as Barnett acknowledges. 2005 WL 357015, at *12.

Thus, there would be no automatic remands, whether based on the

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presence of judge-found facts and the use of mandatory guidelines

or on the simple fact that mandatory guidelines were used as the

basis for sentencing after a jury’s findings or a defendant’s

admissions. Similarly, this approach also avoids treating Booker

error as a structural error that "undermin[es] the fairness of a

criminal proceeding as a whole." Dominguez Benitez, 124 S. Ct. at

2339; see also Olano, 507 U.S. at 735; Arizona v. Fulminante, 499

U.S. 279, 309-10 (1991) (providing examples of structural error).

As in cases of preserved error that we review for harmlessness, the

government will be able to argue the absence of prejudice based on

the entirety of the existing record.

Indeed, this case provides an apt example of that

prospect. Here, Serrano faced a statutory mandatory minimum of 60

months' imprisonment. After taking into account his role in the

offense and his criminal history, the guidelines required (now,

advise) a sentence within the range of 63 to 78 months, leaving

little room for modification between the mandatory minimum of the

statute and the guidelines minimum. The judge sentenced Serrano to

63 months. Even now, the district court "must consult those

Guidelines and take them into account when sentencing." Booker,

125 S. Ct. at 767. The court could have sentenced him below the 63

months of the guidelines only by totally ignoring the sentencing

factors that it is still required to consider. Thus, the

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government could show that Serrano was not harmed by the mandatory

nature of the guidelines.

5. Conclusion

Applying a presumption of prejudice in cases of Booker

error would not be an innovation. As Barnett explains, the concept

is well grounded in Olano and other circuit decisions in a variety

of contexts. Hence, this approach remains faithful to Booker's

directive to the appellate courts to review unpreserved claims for

plain error; it avoids automatic remands; and it responds fairly to

the unique problems left in Booker's wake.

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